Optimizing Life and Finances with Jack Raines

Summary

Masters in Business Podcast – “Optimizing Life and Finances” with Jack Raines

Host: Barry Ritholtz (Bloomberg Radio)
Guest: Jack Raines (Venture Capitalist, Author of Young Money)
Date: August 7, 2026

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Episode Overview

This episode features Barry Ritholtz in conversation with Jack Raines, a venture capitalist at Slow Ventures and the author of Young Money: A Field Guide to Wealth and Purpose in your 20s. The discussion explores Jack’s unconventional career path, key financial and life lessons, the pitfalls of status chasing and FIRE, principles for optimizing time and money in your 20s, and insights from his adventures in travel, writing, trading, and venture capital.

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Key Discussion Points & Insights

Jack’s Early Career and Education

• Background: Jack studied Finance and Spanish at Mercer, played college football, and attended Columbia Business School via deferred enrollment.
• No Set Plan at the Outset:

  “I feel like basically every white dude ends up studying finance unless they're dead set on going to like med school, law school, or like computer science.” (03:33, Jack)

• First Job at UPS in Corporate Finance:
  • Graduated pre-pandemic (December 2019), started work just as COVID hit, went remote after three days in the office.
  • Describes this period as “work from home purgatory”—uninspiring Zoom calls and Excel modeling, not a good environment to learn real-world job skills (04:35).

Global Travel and the Value of Timing

• Catalyst for Change: Used pandemic boredom and a successful streak trading SPACs/Warrants to fund a year of global travel.

  “It gave me more money than I expected to have at 23 or 24. I was like, I mean, it wouldn't cost that much to just go hostel hop Europe and Latin America for a year.” (06:25, Jack)

• Grandmother’s Impact: Early exposure to travel—from safari in Tanzania at 11 to service trips in college—fostered a desire for meaningful, unstructured adventure (06:31-07:09).
• Key Lesson: Life is Stage-Specific:
  • Maximized cheap, hostel-style travel while young—an experience with an “expiration date.”

  • “The biggest takeaway…was like, if I really wanted to do this trip, this was the right window to do this. Like, I optimized that phase of my life correctly … not just being aware of what you want to get out of life, but what things have deadlines.” (11:11, Jack)

On Writing and Finding a Voice

• Started as Financial Writer via Reddit/Pseudonym:
  • Burner Reddit: “Barmelo Zanthony” for trading tips/conspiracy theories; enjoyed writing as catharsis and idea generation (12:20-13:24).
• Rejected by Media Startups → Launched His Own Substack Blog:
  • Blended finance insights and travelogue, monetized via newsletters, built an audience organically.

  • “I just enjoyed it… it's a good exercise for anybody to really distill what you think — try to sit down and put pen on paper.” (13:22, Jack)

• Writing as Discovery:

  “I write to figure out what I think.” (13:46, Barry quoting Daniel Boorstin)

SPAC Trading: Wild Rides and Painful Lessons

• Rapid Success, Sudden Losses:
  • Turned $6,000 → $400,000 trading SPACs and especially warrants but ultimately lost $150,000 in a single trade (17:51-24:36).

  • “The plan was—buy SPACs near NAV, sell when they pump. That was a good strategy…The issue was I was so used to number going up, I was willing to bet the house on doing it one more time.” (25:49, Jack)

  • Learned about risk management the hard way; underscores the irreplaceable education of living through a big trading loss.
• Rite of Passage for Traders:

  “That sort of big whackage is a rite of passage…You could read that in a book, but until you've lived it, it's really challenging.” (25:13, Barry)

Venture Capital, Creator Economy, and New Models for Success

• Pivot to VC at Slow Ventures:
  • Found the job via Twitter DM, joined the San Francisco office after a rapid hiring process (29:37-33:13).
  • VC is open to non-traditional backgrounds, allows for work-life flexibility and supports parallel projects like book writing.
• VC as Sales Job/Relationship-Building:
  “Venture capital is 90% sales… you need to be talking to X number of people and there are metric hurdles…it’s a volume game.” (35:44-36:57, Jack)
• Slow Ventures’ Approach: Avoiding Hype:
  • Stay away from trendy bets (e.g., AI foundation models) and focus on long-term value, consumer tech, and creative entrepreneurs.
  • Early-stage seed/A/focus allows nimble exits and broader shot-taking (38:51-40:08).
• Investing in Creators:
  • Created $64M fund to back creators as holding companies.

  • “People who have a true cult of personality and are a subject matter expert…have a massive advantage…We literally invest in creators like holding companies where any businesses they build off their platform leverage their brand and platform.” (41:54, Jack)

Financial Philosophy: Time, Money, and Purpose

• Time vs. Money:

  “I had considered the opportunity cost of how I was spending my time and I adjusted my life accordingly…Time is finite and how and when you spend it is really important.” (48:40-49:08, Barry paraphrasing/Jack expanding)

  • “There's no saving time, there's no investing time, there is only spending time.” (54:59, Barry quoting Jack)
  • Life’s chapters have windows; optimize experiences during the proper age (“stage specificity”).
• Introspective Pandemic Years:
  • Pandemic forced personal reckoning; isolation and routine became a crucible for realizing the preciousness and fungibility of time (55:35-57:19, Jack).

  • “You become really reflective of how you’re spending your time, what you’re motivated by…At some point you ARE gonna die…Be in control of your time. Don’t be a passive participant in your own life.” (57:19, Jack)

• On Money and FIRE Movement:

  “Money is infinite and fungible. Time is neither. Young people shouldn't penny pinch so much if they have fun, interesting stuff they want to spend the money on.” (58:26-58:57, Jack)

  • Fire movement limits life and can create social isolation:

    “When you make accumulation of capital to escape the labor force an end goal, you just set yourself up to be bored…There are social costs you can’t see on a spreadsheet.” (59:16-60:19, Jack)

Embrace Being Broke (in Your 20s)

• The Advantage of Youthful Ignorance and Flexibility:

  “Many of life's adventures are adventures only because you're 22 and broke and stupid and surrounded by other broke, stupid 22-year-olds. This is a feature, not a flaw. Lean into it.” (60:19-60:39, Barry quoting Jack)

  • Jack’s year of hostel-hopping: embracing serendipity, cheap living, and small hardships as ingredients for adventure and storytelling (61:41-63:43).

On "Pursuing Your Passion"—Cautiously

• Don’t Monetize Your True Passions Too Early:

  “You shouldn't bank your income on a thing you're passionate about. The second your paycheck is dependent on that, it can feel more like a chore than a fun thing.” (64:01-65:35, Jack)

  • Build financial base with skills that pay, then use surplus time and security to pursue passions on the side.

The Barometer of Fun

• Measuring a Life Well Lived by Enjoyment and Growth:

  “If you find joy in the suck, you're probably doing the right thing… The definition of fun changes as you go through life's different stages.” (65:46-67:07, Jack)

  • Experiences that are hard can, in retrospect, be deeply fulfilling.

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Memorable Quotes & Moments (All Timestamps in MM:SS)

• "I feel like basically every white dude ends up studying finance unless they're dead set on going to like med school, law school, or like computer science." (03:33, Jack)
• "The biggest takeaway from traveling was like, if I really wanted to do this trip, this was the right window to do this...Every…thing you do in life has a expiration date for when you would enjoy it the most." (11:11, Jack)
• "The issue was I was so used to number going up, I was willing to bet the house on doing it one more time." (25:49, Jack)
• "There's no saving time, there's no investing time, there is only spending time." (54:59, Barry quoting Jack)
• "Many of life's adventures are adventures only because you're 22 and broke and stupid and surrounded by other broke, stupid 22-year-olds. This is a feature, not a flaw. Lean into it." (60:19, Barry quoting Jack)
• "You shouldn't bank your income on a thing you're passionate about...It can start feeling more like a chore than like fun." (64:01, Jack)
• “If you find joy in the suck, then you're probably doing the right thing.” (65:46-67:07, Jack)

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Important Segments & Timestamps

• [03:33] Jack describes lack of a set career plan; choosing Finance and Spanish
• [04:35] UPS remote work purgatory during COVID
• [06:25] Decision to quit job, travel globally, funded by SPAC win
• [11:11] Discussion on “stage specificity of life” and the importance of timing
• [17:51] The adrenaline and aftermath of massive SPAC trading wins/losses
• [25:13] Barry reflects on trading losses as a rite of passage
• [29:37] Pivot to VC, Slow Ventures hiring (Twitter DM story)
• [35:44] VC is mostly sales: “smiling and dialing”
• [41:54] Creator fund thesis at Slow Ventures and examples
• [48:40] Optimizing time: “I had considered the opportunity cost…”
• [54:59] The nature of time—spend it, don’t dream of saving it
• [58:26] Money is infinite and fungible; time is not
• [60:19] Embracing youthful adventures and being "broke and stupid"
• [64:01] Caution against monetizing passion too early
• [65:46] “Are you having fun yet?” as life’s metric
• [80:27] The permanent, evolving role of retail in markets; cycle acceleration

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Further Reflections & Book Recommendations

• Mentors: Coaches, writers (Morgan Housel, Tim Urban), and current boss Sam Lesson shaped Jack’s career and approach to optionality and fulfillment (68:45-73:17).
• Book/Media Faves: 1873 by Ahmed, Lords of Finance, The Infinity Machine on AI; enjoys biographies, big historical narratives, and select podcasts/films (73:23-76:37).
• Career Advice: Build a visible body of work, pursue prestige for leverage (not for its own sake), and don’t be paralyzed by status games. (77:13-80:17)

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Core Takeaways

• Optimize Experiences for Your Age: Some things can only be fully lived when young, broke, and unencumbered.
• Time is Life’s True Currency: You only get to spend it once; prioritize accordingly.
• Losses Are Lessons: High volatility—whether in trading or life—is where the true learning happens.
• Purpose, Not Just Status or Money: Don’t chase prestige for its own sake; use it as a tool for doing what matters.
• Have Fun (and Redefine Fun as You Grow): A fulfilling life blends fun, meaning, and growth—often through challenging experiences.

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For anyone in their 20s, Young Money and Jack’s journey—part adventure, part cautionary tale, part practical guide—offer a deeply relatable, actionable meditation on how to live, earn, and find purpose in a modern, distraction-filled world.

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End of summary.

Transcript

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[Barry Ritholtz]

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[Jack Raines]

Bloomberg Audio Studios Podcasts Radio

[Barry Ritholtz]

News this week on the podcast, my somewhat special guest Jack Raines is a venture capitalist and author. I've been reading his substack for a couple of years and always found it quite enter interesting. His new book Young A field Guide to Wealth and purpose in your 20s is really interesting and wise beyond its years. I wish I had access to a book like this 100 years ago when I was in my 20s. I thought this conversation was fascinating.

[Vanguard Advertiser]

I think you will also with no

[Barry Ritholtz]

further ado, my interview of Jack Raines.

[Vanguard Advertiser]

Jack Raines welcome to Bloomberg.

[Jack Raines]

I mean extra special guest is way too kind but so my special guest, my normally special guest, I I wouldn't

[Barry Ritholtz]

want to call him like my young guest. My, you know, I, I painted myself into the corner with extra special guests. Once you go that way, you can never go back.

[Jack Raines]

I'll take it.

[Barry Ritholtz]

Here's my special guest. Really? What's wrong with Jack? He's, he's a special.

[Jack Raines]

He's wearing a cowboy hat.

[Barry Ritholtz]

That's right. Well, we'll, we'll, we'll get into that in a little bit. So let's roll back so many years ago to when you're undergraduate studying finance and Spanish while playing football at Mercer. That was before you got your MBA from Columbia. Was there ever a career plan?

[Jack Raines]

Like, not really. It was just, I don't know, I feel like basically every white dude ends up studying finance unless they're dead set on going to like med school, law school, or like computer science. So it was study finance and then I was set to graduate in two and a half years because we had to take summer classes with football. And I was like, I should double major. Finance and marketing is stupid. I don't like computer science. Let's pick up Spanish because it feels like that could be marginally useful living in the South. Spanish is very assay Aussie right now, but it's like sufficient. But there was no real career path other than figure it out from there.

[Barry Ritholtz]

That's intriguing. I'm cracking up because I have so many different ways to go with this. First gig at a school was corporate finance at ups, which you described as mostly moving a mouse around the screen and trying to look busy.

[Jack Raines]

Correct.

[Barry Ritholtz]

Tell us about your experience in corporate finance.

[Jack Raines]

Yeah, I mean, to set the stage a little bit, I graduated in December 2019, which was probably the worst possible date to graduate given that Covid started like three weeks after that. So I moved to Atlanta in January or February of 2020, start working for UPS. I'm in the office for three days, my computer isn't even fully online yet. And then we're told that we're going remote for one week and then one month. And then everybody had the same experience where a year and a half later you're still remote. So I don't think it's great to be a 22 year old who's never had a real job, who's then told you're going to work from home while you have like your Xbox and all of your friends like doing the same thing. And it was actually like a terrible environment to like start learning how to be a worker. And yeah, it was just zoom calls Excel sheets like modeling out fuel cost projections and forecasts for UPS for like 2022. Yeah, I was, I was honestly bored the whole time. And to build on top of that, I had gotten into business school out of undergrad. So at Columbia I would. I went to business school at Columbia and they have a deferred enrollment program where when you're a senior in college, you apply and then you work a few years and go to business school. So I knew that I was going to go to grad school in like three years. Covid hit I was super bored working remote, just doing basically nothing. And it just kind of felt like I was in a work from home purgatory for about 18 months.

[Barry Ritholtz]

So having that window where, hey, I know where I'm going to be 18 months from now in September of 2020, blank. What led you to say, I think I'm gonna quit and just buy a one way ticket to Barcelona and travel the world. Like that's a giant leap, which not a lot of people have the nerve to make. What led to that decision?

[Jack Raines]

So like when I was a kid, I always loved to travel and my grandparents would take me everywhere.

[Barry Ritholtz]

Your grandma took you on a crazy trip you describe in the book to Savannah in Africa?

[Jack Raines]

Yeah, yeah. When I was 11, my grandma, mama Ruth, she. I'm the oldest grandkid in the family and she hit me with the idea that she wanted to take me on a trip like anywhere in the world I wanted to go. I actually didn't know if she literally meant anywhere I wanted to go somewhere crazy like Africa or Asia. And we lived in South Georgia. Initially I pitched Costa Rica and she said, you can? Yeah, she said like that's like a three hour flight. And I was like, okay, Tanzania. I like, I thought the, like I had a big map in my room as a kid. I thought it'd be cool to go to the Agora Crater and see Mount Kilimanjaro and all this stuff. So she took me and we went and we went on a two week safari and it was awesome. And then in college I studied abroad in Spain one summer, I went to France one summer with my best friend from college, I did a service trip to Ecuador. Like I always loved leaving the US and it was kind of a thing in the back of my head where I knew at some point in my 20s it would be really fun to do like a multi month trip abroad with like no itinerary other than just see other stuff. And I was sitting there, it's like you have this, you're working remote for 18 months and you're bored and then I, for better or worse, had a Fortuitous run trading SPACs and SPAC warrants during the pandemic, which gave me enough. It gave me more money than I expected to have at 23 or 24. I was like, I mean, I. I don't. It wouldn't cost that much to just go hostel hop Europe and Latin America for a year.

[Barry Ritholtz]

Yeah, I'm glad you brought that up. You're not a trust fund bud, but, baby, in any stretch of the imagination. No, you scrape together some money, you fly coach, you're staying in Hostels, you have 10 roommates in these places eating

[Jack Raines]

like McDonald's or Euros or whatever every day. It was the best. I mean, I got food poisoning one time. It was fun. It was fun.

[Barry Ritholtz]

More recently, you wrote a story about going to someone's wedding, and I think it was India, and a bunch of people got food poisoning, and it was hilarious.

[Jack Raines]

It feels a little bit like India right now. In New York. It's like the. The air quality today as of recording is pretty similar to New York.

[Barry Ritholtz]

Canadian fires are amazing. You walk out, it smells like a barbecue yellow.

[Jack Raines]

It's like we're microdosing New Delhi air right now. It's great.

[Barry Ritholtz]

It's good stuff, only without the. The E. Coli that, that you described.

[Jack Raines]

Right.

[Barry Ritholtz]

But let's. Let's bring it back to your career. So. So you do this trip, you go through a couple of dozen countries, you meet people that you're still friendly with. It was really fascinating. And you get to business school. How do you adjust? How do you make that transition?

[Jack Raines]

Yeah, it was, it. It was interesting. Like, I. In the back of my head, I kind of knew I had this start date, moving to New York in August of 2022. So I eventually quit my previous job. First job out of College in August 21st. I was kind of like, all right, let's spend a year and just have as much fun as physically possible, knowing that then we're going to go to grad school, then we'll do our career in New York and yada, yada, yada. It was, it was funny because it was at first weird. Like, being like, I. I spent basically a full year out of the country jumping around a lot, and then you're in New York and you have, like a home base and you have a business school is not a particularly strenuous thing, but you do have a set schedule where you have classes and stuff. I loved it, though. I mean, I love Columbia. Honestly. I love New York in general. Best city in the world, particularly in your 20s. And it took a couple of months to really get in the flow of like living here. And then also like you're meeting hundreds of new people like that. But actually getting integrated, not hard. It felt like a perfect fit.

[Barry Ritholtz]

Really, really interesting. So I'm curious, you learn a lot of things in both your office career or remote work from home career and business school. What did you learn about finance, money, time, while you were traveling?

[Jack Raines]

I mean, the, the, the biggest thing that really jumped out was it's something I write about a lot in the book. Like the, I call it the stage specificity of life. But by that I mean that it's, it's pretty easy to conceptualize money. Like, you're taught from like in high school how money compounds over time. If you invested and it's, you know, you should be frugal and save up money. But what, what you miss is like, what's the optimal time to spend that money on different things. And the, the example that I give a lot is like, I was 24 and like sleeping in a bunk bed in the hospital with 12 roommates or whatever. And it was actually just a hilarious setup. Like, it's just a bunch of nonsense. You have a French guy here and then like a Mexican girl here, and it's like half the, a lot of the dorms are co ed and it's like, it's like summer camp for like young ad. But then occasionally you meet somebody in their like early 30s staying in the same hostel, and it's like you can almost tell that they notice they're like, probably six or seven years too late to have done that type of trip. And like the biggest takeaway from traveling was like, if I really wanted to do this trip, this was the, like, this was the right window to do this. Like, I optimized like that phase of my life correctly for somebody who wanted to do that type of thing. And that's kind of what stuck with me the most after, is not just being aware of what you want to get out of life, but like, what things have deadlines where like, if that window of opportunity closes, you're just not going to be able to maximize your like, fulfillment or enjoyment or like, utility from that experience. Like every, basically everything you do in life has a, an expiration date for when you would enjoy it the most. And you have to, you can, you

[Barry Ritholtz]

can go cheap and cheerful in your 20s, maybe even early 30s, but not much past that.

[Jack Raines]

Correct.

[Barry Ritholtz]

So you were also writing before the trip and during the trip Tell us a little bit about your experience, what you discovered about yourself as you're writing and why you thought that might be a career path.

[Jack Raines]

So hilariously, when I was doing the whole SPAC trading thing in 2020 and 2021, I had a burner Reddit account called Barmelo Zanthony. It's a play on words on Carmelo Anthony and Xanax bars. It was my name. In my college group Me, we all had edgy, like drug related, famous and combination names. I was writing so much stuff about like, oh, like Apollo changed the background header of their website from oil rigs to windmills. I think they're going to take an EV company public through a spac and then they announce a deal with Fisker Automotive three weeks later. It was like borderline conspiracy theory stuff, but it worked. A lot of it worked. Yeah. So I like always liked just writing about like stuff I was seeing going on in markets. And then when I was, when I was traveling, I tried to get hired by the morning brewing the hustle, a few different like kind of upstart ish media companies. Nobody would hire me for lack of like professional writing experience. So I just started writing like I just launched a sub stack and started writing a newsletter. And it was like half investing in finance and half travel blog. Like detailing everything I was doing day to day, who I was meeting. And I just enjoyed it. Like it's writing something I've always found fun. I've always found it a bit cathartic, like putting your thoughts on paper. And it's a good, I don't know, I think it's like a good exercise for anybody to really like distill what you think about a thing is try to sit down and put pen on paper.

[Barry Ritholtz]

So Daniel Boorstin, the Librarian of Congress's famous quote, I write to figure out what I think.

[Jack Raines]

Yep.

[Barry Ritholtz]

And besides that though, at that hour the bars are all closed.

[Jack Raines]

Yep.

[Barry Ritholtz]

So you know, until you put it down, until you put pen to paper or fingers to keyboard, it's sort of nebulous and not distinct. Once you write it, there it is in black and white.

[Ad/Promo Voice]

Yeah.

[Jack Raines]

Yeah.

[Barry Ritholtz]

So for sure. So you, you come out of Columbia. What's the first gig you, you're doing while you're, while you're a new grad.

[Ad/Promo Voice]

So.

[Jack Raines]

So to step back a little bit, when I was still in business school, I kind of have this like, I think investing and financial markets are interesting. I really like writing. I had like monetized my newsletter fairly well, selling ads and I Was kind of trying to figure out which way I wanted to lean with it. And then I had some publishers who were like loosely interest maybe writing a book. So I wanted to leave the book writing door open. And I interned for a venture capital fund called Redpoint Ventures my first year, helping them with like building up a newsletter and like editorial strategy and all that stuff. It was like, love the team there. It was great. My takeaway from that was I should either like go do media or I should like push you get in like an investing seat somewhere, not split the middle and do like the marketing arm of an investment group. So going into my second year, Sam Rowe, you know, friend of the show, he was like contracted by Robin Hood to help them with the hiring for they were building out a media subsidiary called Sherwood News. We grabbed coffee and he was like, I don't know what your plan is after business school. I think you'd be a good fit with what they're building here. And he started telling me about it and it checked a lot of boxes of like on one hand it was kind of an upstart new media thing with like, I would have a lot of autonomy. On the other hand we were surrounded by the structure of like a big fintech company. So like media is a tough business these days and like there was a lot more stability there from like financial backing.

[Barry Ritholtz]

Tell me about having a media outlet attached to a large fintech or data services company.

[Jack Raines]

The entire pitch was just trying to like basically make a new age Bloomberg say the truth.

[Barry Ritholtz]

Did. Did you guys get any hood stock?

[Jack Raines]

Yeah, yeah, yeah.

[Barry Ritholtz]

So not terrible.

[Jack Raines]

Not terrible. I mean the issue is I only worked there for a year, so it's not like I got that much but like it. Yeah, Like I, I wish I would have. I wish I would have gotten more and I wish I would have stayed longer had I gotten more is the takeaway from that. But yeah, I ended up, I ended up joining them during my second year. I signed the book deal for that book the summer after I graduated. So about two years ago now. And then I was sitting there and I just like everything was fine but I realized after working in a like more structured media environment, I actually like, like, I like writing a blog. I like kind of free range putting stuff on the Internet. But like I didn't like the actual like, like call it 9 to 5 employed version of like financial media. And my like it kind of clicked in my head that when I was at that point of investing thing versus like media, I actually probably should have gone investing Track. But I was so hyper focused on, like, I don't want to kill a potential book deal momentum and this and that. That I took the other one and I had like a total career panic. Like two, almost two. Almost two years ago. Like fall 24.

[Barry Ritholtz]

And there is something to be said about the Daily Beast that must be fed when you're on a regular deadline. Like that stuff. Yeah, no, it's brutal. And it's why there's so much content that's so useless. Because, hey, there are minutes and hours to fill and column inches and the infinite more of the Internet, I mean, it just never stops. So that's why we have this fire hose. So you had done Young Money as a substack. You had done Sherwood for Robinhood. I'm kind of fascinated by an essay you did. How I lost $150,000 in a day trading SPACs way back in 21. Tell us about your ramp up in the spac world. And then the blow up.

[Jack Raines]

Oh, it was. I mean, it was awesome. Like, like I, like, I was. I don't know if you would have checked my like pulse or stress levels at that point. They were through the roof. But like, it was crazy. So it's like right when the pandemic hit, I thought I was like the next Michael Burry. I had like $10,000 in my checking account. Threw it all in spy puts, they tripled because obviously the market was going to tank. And I was like, yeah, I'm him. And then, you know, Bill Ackman a week later is like crying on cnbc, say the world's going to hell. And I was like, S P is going to like a thousand. Let's do it again. Let's buy more puts. You know, I actually, having not really been an adult during 08, I completely underestimated, like the Fed and quantitative easing and how that could work and how

[Barry Ritholtz]

fast that turn is.

[Jack Raines]

Like, I. My face got melted off. I shorted the actual bottom. And then I basically round trip to $10,000 to 30, back to 10. I have my tail tucked between my legs and I was like, I'm never trading a stock.

[Barry Ritholtz]

Did you ever feel the need to reach over to the wastepaper basket and throw up?

[Jack Raines]

No. But like, if it had been bigger numbers, maybe. So I'm like, I'm never going to trade stocks again. I put $6,000 and I open like a Roth IRA do my one contribution first year as a, you know, adult working, and I don't look at it for a month. And then in May My friend Jake, buddy from undergrad, was like, do you know what a SPAC is? I say, no. And he's like, well, if you buy this Desert Eagle SPAC, it'll turn into DraftKings stock in, like, two months. And I was like, so it's like, like an ipo. And he's like, I don't know, dude. I just saw on the Internet, if I buy this, you own DraftKings. And I was like, okay. I went down the rabbit hole and was looking at it, and it's like.

[Barry Ritholtz]

And it's at par. It's. It's. Before it comes out, it. Was it trading at 25 or did it trade up?

[Jack Raines]

It was trading because. So the.

[Bloomberg News Host]

The.

[Jack Raines]

The par on most SPACs is, like, 10 DOL. Trading at like, 12 or 13.

[Barry Ritholtz]

Oh, really?

[Jack Raines]

Maybe 15. But the warrants had, like, doubled or tripled, right? Because all the warrants have a strike price of 1150. So then I had, like, traded options enough. I understood, like, strike prices, expiration dates, whatever. And the thing that jumped out was that warrants don't expire for five years and they have an 1150 strike price. So I was doing the math, and I. I watched DraftKings after the merger happened. It ran up to 20. The warrants ran up to 8 or $9. You would have doubled on the stock. We would have made, like 9x on the warrants if you bought them at a dollar, like, at peak pandemic collapse. So I was like, okay, this is easy. Well, I was just like, SPACs obviously kind of seem like a bubble right now, because there had been, like, Nikolai Motors had announced a spac, and there were a couple of others. And I was just like, I bet that this thing is gonna, like. This is just gonna be a game for a little while, and if I can just pick the SPAC warrants early, I bet I can make money. So Nikolai warrants are trading at $3. I bought $6,000 worth. I made, like, 12 grand a couple of weeks later. And then I just kept rinsing, repeating SPAC warrants. And like, six months later, I've gone from six grand to 150 grand. And I was like, this is so easy. So then I.

[Barry Ritholtz]

By the way, that. That should immediately set bells off.

[Jack Raines]

I doubled down, though. It didn't set off any bells, because then I was like, okay, it did sell off one bell. I was like, warrants are risky, and if any of these deals collapse as the warrants go to zero, I should start buying the shares as close to nav. As possible. So I was in like online discord chat with a lot of other anonymous people. We built some web scrapers that will pull every SPAC SEC filing. So as soon as a filing hit the press, like trading halts. When news comes out for spac, I would get a push notification, open up the deck, skim it. If it was electric vehicles, marijuana, outer space, sports betting or renewable energy, I would go all in. Unless the, unless the like valuation. The deal was just egregious. I would go all in. And I knew that the stock would probably pop like at least 30 or 40% because they just did every time. So you get in at 11, your max loss is probably like 5% on any trade and you sell at 14 or 15. So you're basically risking 5% to make

[Barry Ritholtz]

40% asymmetrical risk reward. That's what you want.

[Jack Raines]

And I did that like seven times in a row. And then I went from 150 to 400. And like I'd only risked on any given trade like 5% of my portfolio. And they didn't all hit but like enough did that, it didn't matter. And my dad, obviously, I kept telling him what I was doing and I hit like it was February 2021. And he called me and he was like, you should probably just sell and just put it in like an index fund. And I was like, I can do this two more times. I'll have a million dollars at 24. I'm pretty sure I can get there. That, that should have been the screen.

[Barry Ritholtz]

There's the bell ringing that.

[Jack Raines]

And then when he and his brother or talking to me about potentially managing some of our family's money. You shouldn't have your 24 year old kid who just made 6000% trading SPACs touching your grandparents like retirement money. I did not, thankfully. I said, I don't feel comfortable doing that. I'm okay. I was self aware enough to know that that would have been a bad idea. So getting to how I lose the money at this point, way too many SPACs. Shaquille O' Neal has a SPAC. Paul Ryan has a SPAC. Like everybody and their mother has a SPAC. And the bubble didn't pop, it just stopped bubbling because there, there was kind of this pool of money that was chasing every hot spac. And then there's like 100 of them on the market. Somebody announces a deal, the terms are getting worse and worse.

[Barry Ritholtz]

And the value, you're watching this decay in real time.

[Jack Raines]

Yeah. And it was like by April, May of that Year, it's getting tougher and like a deal to get announced, it might jump 10%. But you're just. I was like, I was addicted to the rush. So there's a buy now, pay later company called Catapult. 80% of the revenue came from Wayfair. Obviously a pandemic Dar. And this was at the time when Square bought afterpay for like $30 billion crazy price. A firm went public at like a $30 billion valuation. And like these companies were growing slower than Catapult because Catapult was just a derivative of Wayfair, which is a pandemic darling. They were less profitable. And I was just like, catapult's gonna have their earnings in August. They've had no sell side coverage. I just need like one analyst from like Morgan Stanley or whatever to, to initiate like a buy. The stock's gonna double. I'm gonna buy a bunch of warrants, like A$50 they're going to rip. And then this thing, I'm going to make $1 million on this trade. This thing had already gone public through a spac. Like there was no floor. That deal was closed. It's a normal company, so not your

[Barry Ritholtz]

traditional SPAC trades that you've been doing before.

[Jack Raines]

It had gone public through a spac and it's just like a normal company at this point. And I, I just aped into it with like 300, I think I like $330,000 at that point just went all in. And it started like inching down and spiked back up leading up to earnings. Like I had four different times. I could have gone out with like a 10% loss. And I was just like, I was just pot committed to like, this is going to be the millionaire trade. They missed earnings so badly. The stock fell. I think the stock fell 20% before market opened on like August 11th. And the warrants immediately got cut in half by like 50%.

[Barry Ritholtz]

And that's 150 grand.

[Jack Raines]

Yeah. And I'm just, I'm looking at it, I'm looking at the like level 2 trading data and there's, there's a big buy for like, like 100,000 warrants at a dollar or whatever. And then there's the floor collapses under. And I was like, huh? I'm just gonna, like, I'm just gonna sell to that entire bid and just eat it. And like I'm getting out before like the whole thing gets rug pulled. Which was the right move because I basically liquidated my position pre market went from like $300,000. Like 150 or whatever. And I was just like, man, that sucks. Put it in the S and P and then just went to the gym and worked out for like real self loathing workout for like three hours.

[Barry Ritholtz]

You know that that sort of big whackage is a rite of passage of anybody that's ever worked on a trading desk. I don't care if you're at, you're at Jane street or if you're day trading from home. Those losses are just so seminal and so instructive and focus you on, hey, what's my risk management? What's my edge here? What am I really doing swinging for the fences? Am I really putting 50 or 100% of my portfolio into one trade? That seems kind of like you, you, you could read that in a book, but until you've lived it, it's really challenging.

[Jack Raines]

The issue for me was like the, the plan I had initially of like, buy spacs near nav, sell when they pump was like a good strategy. And if I'd stuck with that, even if it stopped working, it's like, okay,

[Barry Ritholtz]

the downside is de minimis.

[Jack Raines]

We made a bunch of money. This trade doesn't work just like park an index fund until if you move on.

[Barry Ritholtz]

Right.

[Jack Raines]

Yeah. And then like either come up with something new or just stop. The issue was I was so used to number going up, I was kind of willing to bet the house on doing it one more time. Then I'm confident if I'd hit a million, I would have walked away. That was just like a benchmark number.

[Barry Ritholtz]

Oh, you should know that when you hit a million, you would not have walked away. Junkies don't say one more hit and gamblers don't say, I just need this parlay to come in right. And then I'm good. Because you're always looking for the, for the dopamine hit, for the adrenaline.

[Jack Raines]

I would have found something else to speculate on, but I think I would have stopped trading spacs had that happened.

[Barry Ritholtz]

Coming up, we continue our conversation with Jack Reigns, discussing slow ventures and investing in creators. I'm Barry Ritholtz. You're listening to Masters in Business on Bloomberg Radio.

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[Jack Raines]

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[Barry Ritholtz]

Best cheesesteaks in town.

[Jack Raines]

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[Jack Raines]

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[Barry Ritholtz]

Not this onion I'm jabbing.

[Jack Raines]

It's just so beautiful. Oh yeah, nice.

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[Jack Raines]

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[Jack Raines]

And now get early access to our biggest sale of the year.

[Barry Ritholtz]

Save 25% on the new Comfort Next Lux for a limited time only at a Sleep number store or sleepnumber.com I'm Barry Ritholtz. You're listening to Masters in Business on Bloomberg Radio. My somewhat special guest Is that how

[Jack Raines]

you want to be?

[Barry Ritholtz]

Is that how you describe yourself?

[Jack Raines]

Marginally special.

[Barry Ritholtz]

My marginally special guest, Jack Raines is here. He is an associate at the venture capital firm Slow Ventures and the author of the book Young Money, which we'll get to in a few minutes. So I'm kind of fascinated how you pivoted into VC work. You joined Slow Ventures in San Francisco from New York. Did you relocate to San Francisco and then come back to New York? I kind of get the sensure bi coastal.

[Jack Raines]

I try to make it look bicoastal occasionally on Twitter. No, I mean the funny thing was they were hiring in New York and San Francisco and I applied for the New York job. I met with the partner in New York first and then one of the GPs in San Francisco, Sam Lesson. I get introduced to him by the guy in New York and we're on a zoom call. He'd like just come from the gym, super sweaty and disheveled looking and five minutes in.

[Barry Ritholtz]

Are you allowed to Say that. Is he okay with that?

[Jack Raines]

I think he would agree with it. Five minutes, Five minutes into the call, he's like, what do you think of San Francisco? And I said, fentanyl and homeless people. And he was like, it's a crazy answer for somebody applying a job in San Francisco. And I was just like, I didn't, like, I applied for the job in New York, and he was just kind of like, well, I thought I was interviewing you for an SF seat. And I was just like. He told me to, like, take a beat and, like, think about it. And I, I, I can't remember if I told him on the call or just texted him right after, but I was like, honestly, dude, I mean, I want the job. So I, I didn't know this is what I was applying for, but if you hire me, I'll move to San Francisco. And he was like, have you ever visited? And I said, no. So.

[Barry Ritholtz]

But I've been to 25 other countries in 50 other cities. I'm sure I can figure it out.

[Jack Raines]

Yeah. The only difference is San Francisco has so many more AI startup advertisements on the billboards, and they have Waymos, which are awesome. But, yeah, like, I mean, I.

[Barry Ritholtz]

And they are everywhere. We were just San Francisco a few months ago.

[Jack Raines]

They're so sick.

[Barry Ritholtz]

They, they're like yellow cabs in New York.

[Jack Raines]

Yeah, yeah, they're. They're incredible. I mean, the worst thing about New York is that we keep trying to, like, block Waymo's, like, let it happen. I'm. I'm so pro Waymo. I'm like Waymo's biggest fanboy. But, yeah, like, going back to fall 2024, I was in this real, like, kind of career panic. I want to get out of media. And, like, I was like, I should have gone down the investing route. And then, you know, it's like a step back. And I had, like, signed that book deal. I was like, okay, I'm going to have to write a book. I'm going to have to be able to market it. So that means I need to look at jobs where I could still have, like, bandwidth and flexibility to do so, which, like, eliminates a lot of investing stuff where there's compliance issues.

[Barry Ritholtz]

No investment banking, no. No trading on a desk, and no portfolio management or even CFA analysts, where whatever you do is disclosable and requires approval. And it's complex.

[Jack Raines]

But venture capital is, like, the biggest. Like, build your personal brand. Like, content helps you source deals. So I kind of honed in on, and I didn't have, like, an investment banking background. VC is more open to non traditional investing backgrounds. It just kind of made sense. And I had a decent network in that space from like Twitter and writing and all this stuff. So I just kind of started pounding the pavement, like reaching out to vcs. I knew in my network that may or may not be hiring and slow happened to be hiring. And I messaged, hilariously, I messaged Yoni, the partner in New York, on Blue Sky. That was back when everybody thought Twitter was going to die. And Blue sky was.

[Barry Ritholtz]

Blue sky didn't take off. But it does feel like Twitter is kind of ground to a shell of

[Jack Raines]

what it used to be. I think it's starting to come back as of like a month ago.

[Barry Ritholtz]

Oh, really?

[Jack Raines]

It feels like they changed the algorithm where you can like see your mutuals again. So people.

[Barry Ritholtz]

Oh yeah.

[Jack Raines]

Literally last week, Nikita Beer tweeted, they tweaked the algo so like you're seeing your mutual followers. And I was like, dude, that's what it should have been the whole time, right? But anyway, I basically got hired from a Twitter DM and then a last second flight to San Francisco.

[Barry Ritholtz]

Six weeks from application to starting in in sf, basically.

[Ad Details Voice]

Yeah.

[Jack Raines]

Like, I, I didn't know where to live. I went on the Facebook marketplace, found some dude with an open room and just hopped on a FaceTime with him. And I was just like, yeah, like, I guess I'll just take the other half of your apartment. And then I moved there. That was. I just put my stuff in a suitcase and just flew out.

[Barry Ritholtz]

So are you New York based today?

[Jack Raines]

I live in New York now. I moved back here a few months ago.

[Barry Ritholtz]

All right, and. And how do you, how do you work that out if your core office is San Francisco?

[Jack Raines]

So we have an office in New York too. Flatiron. So 20th and 5th. It was one of those things where we were pretty async in San Francisco. Like we, we have an office in downtown sf. I was going in probably four days a week. So like some people are going in a lot. My boss lived in the suburbs a little bit. He would come up sometimes, but I would like take the Caltrain down to like Hillsborough area and like go to his place to work from his pool house with him. It was a funny setup, but it was like we were async enough. And I also knew that like, long term I was going to want to live in New York. I just pitched them on moving back and then flying out to San Francisco like every three weeks or so. And that's the Setup I have now,

[Barry Ritholtz]

New York has a pretty robust technology.

[Ad/Promo Voice]

Yes sir.

[Barry Ritholtz]

I mean we all think of, of San Francisco for AI computer mobile tech, in Boston for health care tech. Where does New York land in that, in that list?

[Jack Raines]

It's, it's. I would, I would put New York

[Barry Ritholtz]

is the like pretty fast rising right

[Jack Raines]

on for like consumer tech. I would argue it's like number one or close to it.

[Barry Ritholtz]

And then you got a big Google office here, you got a big Microsoft office here, you got a giant Amazon office here.

[Jack Raines]

Well, and like anthropics opening like a 16,000 square foot, like they're opening a mass office in Hudson Square.

[Barry Ritholtz]

Like you're, there's some space there.

[Jack Raines]

A lot of, like, a lot of, A lot of what keeps happening is like all these AI companies start there and then as they move into like bigger and bigger, like enterprise commercial business, they expand to the east coast. And like there's a lot of like sales teams on the east coast and engineering town on the west coast. New York's also like a more social, outgoing city where a lot of the like, like sales and go to market. People would prefer to live here. San Francisco is more insular and it's like there's just engineering talent from like Stanford, Berkeley, whatever that aggregates around the bay. So it's honestly a big part of like engineers end up on the west coast and then a lot of the salespeople end up on the east coast. A lot of the customers are also on the east coast.

[Barry Ritholtz]

So really interesting. All right, so I got to start with a few quotes of yours and we'll plow through a lot of that. One of the things though that, that you said a quote of yours. Junior investing jobs at VC mega funds are really just cold calling. Yeah, I don't think a VC in those terms. Explain. Are you really just smiling and dialing

[Jack Raines]

like a little bit. It's funny, like I don't know if you read Bill Gurley's new book, Running out of Dreams, so he said something similar where venture capital is 90% sales. And it really is like.

[Barry Ritholtz]

But that's true about everything in finance and I don't know about outside but, but everything in this space is you're ultimately asking someone to trust you and give you their business.

[Jack Raines]

Yep, yep, yep. Vc, especially at the big, I guess like slow is a fairly small fund, right? Like we have like total team is like 15 or 16 people. Investment teams like nine or 10 people. But like some of the bigger funds, like I have some buddies that have worked at the like call it some combination of like the general catalyst type, A16, Z type, whatever. It's just a machine. Or like inside is like this too where like you are managing just like tens of billions of dollars or whatever and there's so much coverage that it's. I was a little tongue in cheek saying that it's like cold calling, but it is very much like you need to be talking to like X number of people and there's like metric hurdles on like touch points and stuff. Like it's not that there's no discernment or anything like that, but it's a volume game and they need to wrap

[Barry Ritholtz]

it up and they really do try and quantify it and turn it into.

[Jack Raines]

Yeah, it's you. The name of the game is you don't want to miss anything that could be something. Therefore like people should be pounding the pavement making touch points with anybody who could be starting an early stage tech company now.

[Barry Ritholtz]

Slow Ventures kind of famously avoids the trendy hot stuff. No robots, no AI foundation models. What are you looking at at work that's kind of interesting? What do you guys get to see that most people are overlooking?

[Jack Raines]

So it's funny, we actually, we actually just announced one that's like robot E doing like, like warehouses and fulfillment for e commerce companies called Cytronic. So we do occasionally touch, they don't make.

[Barry Ritholtz]

But you're not doing the human form robots, right?

[Jack Raines]

We're not doing any of the stuff that gets clowned on Twitter because you can't fold clothes or do dishes. Right. I mean it's. We're like broadly generalist. We've done everything from like we've done just to name some companies over the last 10 or 12 years, like Robinhood, Slack Allbirds, before they pivoted to being an AI GPU company back when they sold footwear. I mean we have like a hilarious one Meme Lords Technology where it's basically a software platform. It's like a basically marketing tool platform. But for creating memes. I mean we'll do a little bit of everything. We've done crypto stuff, we have done some like vertical AI stuff. We just like making our calling card. We're not chasing the AI hype. The way that we broadly think about it is there's a lot of VC deals that are trades that are now marked up a lot. But do they have terminal value and would they get supported in public markets? You don't know a lot of early stage investors that have played those and then sold when bigger funds come in. At the multibillion dollar valuations have made a lot of money. So you could argue we should have played that trading game. The bet that we're making is go for the stuff that's going to compound long term value. That could be like a standalone valuable entity.

[Barry Ritholtz]

How does the sort of dearth of IPOs, although we're in the middle of a period where there are suddenly a spate of them coming out and more and more companies choosing to stay private for longer, how does that figure into the VC calculus of hey, we eventually want an exit and we can't rely on someone else either from a bigger firm taking this over or some M and A to to give us an exit.

[Jack Raines]

It's interesting. I almost think you have to put VC in two buckets at this point where you have like we play at the really early stage, which also gives you like a lot more opportunities for exits. Whether you sell stakes to like a later stage, bigger growth, like a bigger growth investor once they're in the unicorn status or you get the acquisition or IPO. If you're getting at a company that's worth 20 or $30 million, there's just like a lot of ways you can get paid on that versus you have companies like, like Thrive is probably the most famous one where they manage like $50 billion. Now they own a massive slug of open AI. Like they take really big bets in companies that are like it's worth 10 billion or 100 billion, we think it can be worth 100 billion or a trillion. So for us we have a lot more flexibility on exits, which is like good because we can be more nimble.

[Barry Ritholtz]

You're primarily seed in A rounds, but you're not doing B rounds.

[Jack Raines]

Or we occasionally will with follow on capital, but it's like 95% C and A. So that's like that's our sweet spot. And then so I think for funds like that, I think people like a lot of early stage funds should get more creative. Where can you exit into a big growth fund coming in at like a $5 billion valuation from portfolio construction? Maybe you should. With the mega funds it's like, okay, if you're going to do that, you can't really index all of the like five or $10 billion unicorns because a lot of those, those paper marks would never get support in the public markets. But Thrive, going really deep on OpenAI or Spark Capital going really deep on Anthropic, those are going to go out at potentially trillion dollar valuations. The math works. If you invest $40 billion across a few big funds and something at a $200 billion valuation and you get a 4x or 5x, you're returning tens of billions of dollars. Right. So it's like at the early stage, should probably be looking to sell and some, some of those later stage companies coming in at the later stage. It's like stock picking. You're basically running, you have to run a concentrated book of like There might be three or four private companies at any time. Like a Space X OpenAI anthropic that could go out at a multi hundred billion dollar valuation. You have to be concentrated in those otherwise the math is going to work. If you get those right, you can like 2x3x a fund. If you don't, you won't.

[Barry Ritholtz]

Hmm, really kind of interesting. You come out of the creator economy Slow Ventures has been a player in that space. How does, how does your experience help you as a vc? And what is Slow Ventures see in that space that you know, the traditional venture capitalists overlook.

[Jack Raines]

So to give like a little more color on that, we have, we have a separate fund we raised a year ago called our Creator Fund where $64 million we invest directly in Creat, meaning like YouTubers, podcasters, could be newsletter writers. Our bet on that is that like distribution compared to like technical abilities is getting increasingly valuable where for two things. One, it's easier to build stuff like software because of AI coding assistance to the Internet is so loud now that having like a cylinder of trust from your audience gives you a massive selling advantage because it's so much harder to get attention with like like paid ads and growth hacks and all this that we, we have this and like Sam, my boss was kind of came up with this idea a few years ago that like he calls it almost investing in cults. But people who have a true like cult of personality and are a subject matter expert in a particular theme or vertical have a massive advantage on like marketing and selling. So we raised a fund where we literally invest in creators like holding companies where any businesses they build like off their platform that leverage their brand and platform and all this stuff.

[Barry Ritholtz]

These are 360 deals, covers everything that person does.

[Jack Raines]

Yep, yep.

[Barry Ritholtz]

We basically could be a podcast, could be substack, could be all of those.

[Jack Raines]

Yeah. And like we aren't really that interested in like how money they make from like ad revenue or like platform revenue or whatever. It's more so. For example, the first deal we did was with this woodworking creator named Jonathan Katz Moses and he has a like he has a massive YouTube channel. He's basically.

[Barry Ritholtz]

I know that show. It is so shockingly intriguing.

[Ad/Promo Voice]

Yeah.

[Barry Ritholtz]

Watching this guy build stuff from scratch. Yeah, he's like, it's relaxing too.

[Jack Raines]

Yeah. He's a super compelling guy, incredibly talented. And he's equally good as both a content creator and as an entrepreneur. Like, he has a business that's like making like millions of dollars of revenue.

[Barry Ritholtz]

So he builds various things and sells them.

[Jack Raines]

He.

[Barry Ritholtz]

So he also generates revenue from the YouTube.

[Jack Raines]

Right. And it's like a. Specifically has like a tool on called KM Tools. And. And we invested money in his holding company and that can go toward hiring people to help with the content development, editing, content creation. So we can increase velocity of putting out YouTube videos. Also more people to help rolling out new products and a wider product suite of tools. So the bet is that you put money in that and maybe the tool business really blows up and then Black and Decker type of company acquires it. Or maybe he launches like another business vertical office platform that we have exposure to. So it's. But his whole thing is like woodworking, woodworkers. He'll go to like a woodworking festival in Texas. People come out like to come like, get him to like sign their autographs. Like, he, he just has a lot of clout in that space. So finding people like that in different verticals that we think have like really compelling opportunities to scale big businesses through that vertical in that audience is like interesting. And historically people have been very hesitant to back creators or they back like one business. Like Mr. Beast has a bunch of different businesses. If you back Beast Burgers didn't really work that well.

[Barry Ritholtz]

Right.

[Jack Raines]

If you were backing Mr. Beast as a whole, like Jimmy's entire empire is worth like a billion dollars or whatever. So you want to be like aligned where if they want to change their focus, like our capital is still aligned with that. Like, you don't think this, this experiment's working? Move to this one.

[Barry Ritholtz]

And I think it's called cdc. If you haven't seen these computer controlled woodworking lathes and carves and they're just astonishing. People like you think of carpentry as kind of old school. It is not. It's really fascinating. Coming up, we continue our conversation with Jack Raines discussing his new book, Young Money A field guide to wealth and purpose in your 20s. I'm Barry Ritholtz. You're listening to Masters in Business on Bloomberg Radio.

[Bloomberg News Host]

The Big Take podcast from Bloomberg News keeps you on top of the biggest stories of the day.

[Barry Ritholtz]

My fellow Americans this is Liberation Day.

[Bloomberg News Host]

Stories that move markets Chair Powell opened

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[Jack Raines]

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[Ryan Reynolds]

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[Barry Ritholtz]

I'm Barry Ritholtz. You're listening to Masters in Business on Bloomberg Radio. My pretty special guest. My kind of special guest.

[Jack Raines]

Somewhat special.

[Barry Ritholtz]

Somewhat special guest. I'm gonna write that down. My somewhat special guest is Jack Raines. He is a associate at a venture capital firm and a author. I've been subscribed to his sub stack Young Money for I don't know how many years has that been around?

[Jack Raines]

Four or five years?

[Barry Ritholtz]

Let me know when you get to 30 and you'll be on to some.

[Jack Raines]

Yeah, yeah.

[Barry Ritholtz]

But his new book, Young Money A field guide to wealth and purpose in your 20s, I was really taken by it. Not only was it a fun read, but I just, I not only laughed throughout because I just recognized, oh, I did that dumb thing. But it also is so wise beyond its years. It's hard to imagine that the guy who wrote this was 2627 when he wrote it.

[Jack Raines]

27 and 28.

[Barry Ritholtz]

27, 28 now. Last year of your 20s. Yeah. So I really found it a fun, enjoyable Read about a space that I normally don't play in young money. And there's so many things to talk about with this, starting with quote.

[Vanguard Advertiser]

I had considered the opportunity cost of

[Barry Ritholtz]

how I was spending my time and I adjusted my life accordingly. So you're giving the whole game away on page 13, you basically say, hey, time is finite and how and when you spend it is really important. Tell us a little bit about how you reach that insight back when you were in your early to mid-20s.

[Jack Raines]

Yep. So I mean we talked about the SPAC trading thing earlier, but like when I was 23, mainly 23 and a little bit 24, my life basically looked like this. It was, you roll out of bed, throw on some sweatpants, grab Chick fil a for breakfast, and then you're just like kind of responding to like slack messages. You're on Zoom calls, spreadsheets, PowerPoints, and you're doing all of it from your bedroom. And it had been like that for well over a year. And then on the side like you were over here, like you know, training options. Before we jump on this, I had like my work laptop here and then I have my personal laptop here. It's like, huh, interesting. Like this stack just got announced so I was, I was spending like, I was like basically fake working while just trading stocks all day. And then like in the evenings I, you know, you have like your entire net worth and some speculative spac and you're, you can't even sleep straight because if futures tank you think you might lose a hundred thousand dollars. And so I was almost in this like self induced holding cell of like, I couldn't go anywhere really because of COVID and I was stuck at home and then I was just watching screens all day and thankfully I made some money from it. But I just became really aware around the time I was about to turn 24 that I had just spent the whole last year of my life not really doing anything. Especially like, call it like personal relationships, whatever. I was probably a pretty terrible like boyfriend, friend, checked out, son, grandson. Like, I just wasn't like, I, I was not in control of how I was spending my time at all. I was kind of like a, a prisoner to like work and Covid and stock market.

[Barry Ritholtz]

Which is kind of crazy because during the pandemic you're no longer commuting, you're no longer on the same schedule. If, if any of us had a little more prescience, we really could have taken full control of our day 100% because nobody's looking over your Shoulder at what you're doing. You could come and go as you want, as long as you got your work done. Whenever, however, everybody was fine.

[Jack Raines]

Yeah. Which is so. I mean, to the stock trading thing, I did, like, that would not have been happening if I was in the office, probably at least not as much.

[Barry Ritholtz]

But what was fascinating as I was reading this because I started out trading is you. You nailed the phrase you're a prisoner to the screen. You really can't leave your desktop if you're on a desk. At least someone could watch a position for you. Hey, I got to go. Leave for 10 minutes. Can you make sure this doesn't blow up on me? If it hits this, get me out. You could do that. But if you're doing this from your bedroom and you have a lot of positions on you, you have no other bandwidth for anything else.

[Jack Raines]

It's just push notifications on for everything. You go to the gym, you're checking your phone every two minutes. It was just, like, a little bit nauseating and exhausting. Yeah. And, like, I honestly just felt pretty, like, mentally exhausted from the, like, always being on, and I just kind of had enough. And I also found my job pretty unfulfilling, and I knew I was going to leave it in a year. And it was just like all of these things came to a head, and I was like, okay, like, let's be really intentional here about, like, how do I want to spend, like, if I know I'm going to grad school in a year, like, how do I actually want to spend the next years? Keep going in the motions of the job that I know I'm going to leave to go do something else? Is it like. Like, try to, like, trade back the money I just lost when that trade gone wrong? The thing I kind of wanted to do is, like, honestly just go have an adventure, having just been cooped up for a year and a half. And, yeah, so that, like, it was just like, all of that came to a head, and I was like, I should just. I mean, it's like the opening line of the book. Just blow up my life and go do something crazy. And that's kind of what I did. And I went to Barcelona.

[Barry Ritholtz]

You hit the eject button, you. The concept of time comes up over and over throughout the book, both generally and specifically. One of the things you write about is defining decades differently and about the opportunity cost of your 20s. A lot of people who just buckle down and grind it out through their twenties, you say that for many people, that's a trap smart 20 somethings fall into discuss that.

[Jack Raines]

So I, and I think this is especially true in the like call it hyper competitive, like New York, San Francisco, maybe like Chicago, D.C. area areas where you're surrounded by very smart people who went to really good schools and they go into like at least for like a early 20 something high paying job. But you're also objectively pretty stupid. You don't know anything. You like don't like no. 22, especially guys like, we're all pretty stupid. Yeah.

[Barry Ritholtz]

And tell me when I get to grow out of that.

[Jack Raines]

I don't know. I mean you tell me, you're sitting there and it's like, okay, like what do I optimize for? And the obvious thing is money and the like derivative of that is status. Right. Where high paying jobs are typically higher status jobs. And I think it's when you don't have anything else, it's like, like a North Star. You kind of go for like the like ambitious thing that will pay you well. That sounds impressive over and over again. And like, to be totally clear, there's nothing wrong with that. And that's also much better than like being a bum not doing anything. But you almost, if you fall into that trap of like having some expectation of what you should do without it actually being like your own original thought, like, oh, I want to go do this, you almost become, instead of being like the protagonist of your own life, you're just kind of like filling a preordained role. Like you're almost like an actor. Right. Is how I think about it in someone else's play. Right. And I think the thing like, I think the implicit bet people are making when they do that is I will earn enough money and hit a level of stability where I can hit eject, which you can do, but you can't buy back the opportunities that you would have had in your 20s when you're in your mid-30s.

[Barry Ritholtz]

So another quote, there's no saving time, there's no investing time, there is only spending time. And sentences like that is why I say this book is wise beyond its years. Because I know people who figure that out in their 50s, 60s, 70s, not in their 20s. So kudos to you for getting there. Tell us what led you to that conclusion and how much did the pandemic lockdown accidentally lead to these insights?

[Jack Raines]

I think I became much more introspective much younger because like you just, I mean I had roommates then. Like I just wasn't spending like that much time in a normal day to day and Like, I'm a. I'm a very, like, sociable guy who, like, likes to hang out with people during the day. That gets removed, and you're just in your head a lot, and you become really reflective of, like, how you're spending your time, what you're motivated by. So it was just like this. Again, I don't like this book. Probably wouldn't have happened if Covid didn't happen, because most of these, like, reflections were downstream of this whole just being, like, kind of in, like, an isolated stage of life at a point where, like, you should really just be, like, in an office grinding. So I think that was a big part of it. Hilariously, I, like, I mentioned, like, the second chapter of the book. I used to be terrified of flying, and, like, I'd fly all the time now, and I don't care. But for some reason, turbulence just, like, kicked my. When I was younger, and I. I was on a flight to Colorado about a year into the pandemic for ski trip. Plane was basically empty. It was awesome. We had a super, super turbulent takeoff, and it was just bumpy from Atlanta basically all the way to, like, Kansas City. And I was just sitting there thinking the whole time, we're totally dying. This thing's going down. We're gonna die. Like, It's. I'm. I'm 23. It's over. I'm dead. And we obviously landed. I didn't die, but, like, some. Again, totally random, but just something about that put that thought in the back of my mind, like. Like, well, like, at some point you are gonna die. It's not. Like, up until then, I just thought I was gonna live forever. Like, that's a. Not stupid.

[Barry Ritholtz]

But you don't really think about that in your 20s. When most people are in their 20s, they're immortal. You're not thinking about, well, one day I'm gonna die.

[Jack Raines]

Yeah. And that became like, a forcing function for, like, okay, let's work backwards from. I finally got over the fear of flying, but it's like, all right. Like, we are, you know, Know we're on the clock, and what do I want to do with it? And so it was like a complete fluke from a turbulent flight. Kind of forced a lot of introspection that had been bubbling under the surface for probably the prior year. I was like, all right. Like, I should be doing what I want with my time rather than just letting inertia kind of do its thing. And it was that, like, call it, like, awareness of mortality that became, like, a forcing function for basically what I've done in the last four and a half years since then. Like, be in control of your time. Don't be like a passive participant in your own life.

[Barry Ritholtz]

The difference between money and time is that money is both infinite and fungible. Time is neither. This, this is a philosophical concept.

[Jack Raines]

I consider myself a bit of a philosopher.

[Barry Ritholtz]

Okay, I'm with you. You, I'm there with you. What's your conclusion when you realize that money is both infinite and fungible?

[Jack Raines]

I think you, like, need to be really aware of how much money it takes to get what you want out of life at various life stages. To your point earlier, you can kind of scrape by in your 20s, maybe early 30s, and like, still enjoy yourself. And the older you get, the more expensive it gets. Ideally, you're making more and more money over the course of your life as well. So, like, my consumer conclusion on that is it's like counterintuitive financial advice. But like, young people shouldn't penny pinch so much if they have like, fun, interesting stuff they want to spend the money on.

[Barry Ritholtz]

The.

[Jack Raines]

The caveat to that is, like, you should put yourself in a position where there are like, high income outcomes from that over time. But, like, it's okay to be 25 and not be rich if it means, like, spending money on fun stuff with your friends. Right.

[Barry Ritholtz]

So you're not a fan of the fire movement, the early retirement movement?

[Jack Raines]

Not when it's taken to the extreme. I think that the core idea of like having enough money saved up where like, you control your own destiny, is healthy and good and admirable. I think when you make the accumulation of capital to like, escape the labor force as like an end goal, you just set yourself up to be bored. And almost beyond that, when you like over optimize for fire and your whole thing is like, I want to opt out of work work. You're probably going to hit that in your, like, early 40s when all of your peers are peak work. You're not going to be able to relate to anybody after a couple years against. There's, there's a lot of. I think when you take the fire movement too far, there's like social costs to that that are harder to see when you're looking at a spreadsheet. But it's just like. And you have to forego so many things you would probably prefer to spend money on in your 20s and 30s to hit that it's just not. I don't think you should like, go into crazy debt and you should max out your 401k if you can and all this stuff. But like, like, you just, you shouldn't pass up on life to accumulate cash to be able to opt out of another part of life. Being work is kind of my take on it.

[Ad/Promo Voice]

Now.

[Barry Ritholtz]

That makes a lot of sense. I love this quote. Many of life's adventures are adventures only because you're 22 and broke and stupid and you're surrounded by other broke, stupid 22 year olds. This is a feature, not a flaw of being young. Lean into it.

[Jack Raines]

Yep.

[Barry Ritholtz]

Tell us about how you, you saw that. What is it about being 22 and broken stupid that has to be embraced?

[Jack Raines]

So like, I mean, I spent that whole year of being, I guess I was technically 24, but I was with a lot of 22 year olds who were like, this whole like hostile hopping thing is hilarious, right? Because it's basically a bunch of kids, like studying abroad. It's a bunch of people fresh out of college, but it's a bunch of Europeans taking a gap year, a bunch of Americans fresh out of college, and then a bunch of like 23 to 26 year olds who worked for a couple years and took a break. And you're all just like in bunk beds. Everybody has a shared goal of like, I'm just trying to have cheap fun for a little while. And it makes every situation really, really funny. Like some guys like want to go from Sevilla, Spain to Paris and they're trying to game out like it's $200 to fly, but if we take a train ticket and sleep in a train station for six hours, we can get there for $12 and.

[Barry Ritholtz]

And avoid a hotel room, right?

[Jack Raines]

And avoid a hotel room and extend our European trip like eight more days, right? So.

[Barry Ritholtz]

Or you have like, you did that, right? You went from Barcelona to, to where in Europe?

[Jack Raines]

I mean, I, I covered. I was there from August to December, and then I went to Latin America a month later for a few months and back to Europe. And then that August to December thing, I think I went to like 19 different countries in four months. And it was just, there was no itinerary. I would just go somewhere and then I would meet some people and they would say, hey, dude, we're going to Prague next. You want to come? And I was like, sure, sure. I meet this guy in Prague. He's like, yo, I heard Budapest is great. I'm like, all right. And then somebody's like, we're going to Krakow, Poland next. I met a kid at a hostel in Krakow who pitched me on a startup in San Francisco a year ago, like, talking about weird stuff, small world stuff. But it was just like, I went like pure optionality for a year and it was just like, anybody I meet interesting that's doing something cool, I'm gonna go with them. Like, oh, I heard Tromso, Norway. You can see the northern lights. Let's go dog sledding up there and like do that. So the, the, the ability to just like cast a really wide net. Because when like cheap thrills are fighting, like having to sleep on a train or like have a bunk bed with a stranger, it's just like, like it's fine. Like when you're, when you're a kid, you just don't care. I, like, I'm still in my 20s now, but that would just sound awful. Like I don't want to be in a room with like 12 strangers and worry about my stuff getting stolen. That sounds terrible.

[Barry Ritholtz]

But when you're 24, you got nothing to get stolen anyway.

[Jack Raines]

Yeah, it's like, what were they gonna take my backpack? I had a couple like Zara T shirts and flip flops. Sick. Like, I'll go play poker and win 20 bucks and go buy another one. It's fine. So, and there's versions of that play out with everything, right? Like I'm, I, I, I don't think everybody has to go backpack Europe, but like, you got to San Francisco and there's like 24 year old startup founders that are sleeping in the office with a bunch of their buddies and they're having a blast. Like, they're in objectively, like horrid living conditions. They don't even notice because they're like 23 or 22 or whatever. Like, you can, you can just really lean into like adverse living conditions and find them enjoyable rather than like, they don't like, take away from your life. They create really funny stories.

[Barry Ritholtz]

I'm always fascinated by the pursue your passion recommendation that so many people make. You say pursue your passion is terrible career advice. Yeah, give us some color on that. So like, and you're giving this from someone who is pursuing their passion.

[Jack Raines]

So my, my, like, more specific take on that is you shouldn't bank your income on a thing you're passionate about. The example that I give is like, I love writing. It's a, it's a thing that, like, I've enjoyed. I'll do the rest of my life, whether it's books, blogs, like, it's something I'll always incorporate. My like, initial job out of business school was columnist, podcast, or media Guy like an, effectively a media startup. And I actually found it stressful where like every single day I had to like, put something out. And then I also was sitting there thinking, this is draining the thought of like writing. Like, I wasn't monetizing my blog, it was just a thing that I like doing. And all of a sudden now I don't have energy to work on that fun thing because I spend all that energy on the thing I'm paid to do. So the issue with like chasing your passion is one, a lot of passions aren't that lucrative. Two, the second, your paycheck is dependent on you doing that thing over and over and over again. It can start feeling more like a chore than like fun. So the, the actual advice I have is like, pursue stuff that you're pretty interested in that can pay you. Whether or not you're like, most jobs are boring for a lot of the time. So whether or not you're passionate about it, a thing that you're like interested in and like have an inclination for and have some skills at, go do that for a career and then use that to like subsidize your ability to work on the fun stuff. Like I, you know, like, writing a, writing books and blogs is like a thing I want to do independent of the financial outcomes from it. I pivoted from media to venture capital because, like, I like the offshoot opportunities of investing and tech companies. And that's just, just like a better world to be in for a career path.

[Barry Ritholtz]

Last question before we get to our favorite questions that we ask all of our somewhat special guests.

[Jack Raines]

Somewhat special guests.

[Barry Ritholtz]

How do I know I'm making the most of my time?

[Jack Raines]

So the last chapter of the book is called are you having fun yet? Which I think is like, I think fun is an underrated barometer that you're actually doing the right stuff with your life. And it sounds silly at like first glance, but my take on it is, I think the definition of fun and what you find to be fun changes as you go through life's different stages. Where when I was like 23 or 24, it was just doing dumb, hostile hopping stuff and like getting drunk all the time or whatever. And it was great. Now I get drunk a lot less of the time. It's still slightly, a little bit more refined though. But like, you know, once, once you get a little further in your career, like having real career success and making strides is like a source of like, joy and personal achievement. When I was in college and playing football, like football objectively Sucked. But like I like playing college football really sucks and anybody who's played it will tell you that. But it's like by the way the

[Barry Ritholtz]

description of the workout routines and the 6am wind sprints and, but, but when, you know, deep into the season, the coach tap reigns, we get in there.

[Jack Raines]

Yeah, it's like, it's like an incredibly like fulfill. Like it's like, like, like going from a walk on to be putting on scholarship and then like getting made team captain my senior year. Like that was a much cooler fulfilling moment than like anything I did before or after it. Like I think it was because it was really, really hard. Right. So.

[Barry Ritholtz]

And a real sense of achievement.

[Jack Raines]

Yeah, like it was, it was a, it was a hard thing and I'd like executed on it. So. But it was fun. So my kind of definition of fun is if you like find joy in the suck, then you're probably doing the right thing. And like, like that could be being like groggy and hungover like on a park mentioned Spain, but you feel like you're living out an adventure or it could be like going after like a really ambitious career and like excelling in it. And it's, you know, I think a lot of people as they get further in their careers, they keep chasing that ambition high off of that to the detriment of like their family or other parts of their life. I think a lot of young people like just start like I, I, I think the biggest mistake you can make is like keeping a prior version of you like benchmark or idea of what they should be doing with their time and trying to like force apply that to a future version.

[Barry Ritholtz]

Always evolve it over time or trying

[Jack Raines]

to pull forward a future version too early in your life at the expense of the fun stuff you want to do now. And I think just having a very, very strong sense of like what are the most important things right now that bring me fulfillment and then going after those is the recipe to a good life.

[Barry Ritholtz]

And the sequel to this Find joy in the suck is a great could be title.

[Jack Raines]

Maybe I should call like middle aged money once I get to my 30s and 40s.

[Barry Ritholtz]

Well you could do something every decade. You have a built in model.

[Jack Raines]

Young money, slightly older money.

[Barry Ritholtz]

Right.

[Jack Raines]

Middle aged money.

[Barry Ritholtz]

You got a whole run of things.

[Jack Raines]

Yeah.

[Barry Ritholtz]

All right, let's jump to our favorite questions that I ask even my somewhat special guest. Starting with you're, you're still young. Tell us about your mentors. Did anybody really help shape your career?

[Jack Raines]

Yeah, I mean the, the early mentors would have been football coaches in high school and college defensive line coach Harold Brantley. He was the man. Like he, he was, he was actually one who pushed me to the point that I could play in college in the first place. And then my college defensive line coach, Kenny Baker was like, I was. I came into college playing in a small private high school and thought I was the. And then I got to college and just got wrecked for like a good year. And I was like really bigger, faster,

[Barry Ritholtz]

stronger, or you just didn't know the game as well and didn't have the skills or some combination.

[Jack Raines]

Like, it was like I, I just had to get better. It was like better shape, better skills. I needed to get stronger and just be able to like react to the game on the field way faster. And I just wasn't. The, the processing speed and the just size weren't there yet.

[Barry Ritholtz]

People don't realize the, the quality of play at the college level. It's astounding.

[Jack Raines]

We, we played. So we played Alabama, Little Mercy University. We played Alabama and Auburn in the same year. I like you want to talk about seeing like, like, like monsters. We almost beat Auburn. We were down 7 in the fourth quarter, but Alabama Jalen Hurts Tua Mac Jones smoked us. They had Calvin Ridley all pro receiver who briefly had a gambling problem, but he's back as their punt returner. Guess who started on the punt team, was getting juked out of his shoes like 20 times because we punted so much. Me. But defensive line coach Kenny Baker was like, he, I worked really hard and he could tell I did and he was very encouraging and that like, keep the work ethic up and like, you will develop, like, you will catch up to the point that like, if you keep that work ethic, you'll be able to play. And he was right. By my third season, I was, was decent and by my last season I was objectively good. Like I was never going to be an all American, but I was like a starter and was like a very solid player. But I could have easily quit and transferred to Georgia and like, you know, done the fraternity thing in SEC school, which would have been short term more fun, but long term less fulfilling. So football coaches, post, post school, it's funny, like, especially with COVID my early mentors were like kind of people I found through Twitter. Like, I remember when I read the Psychology of Money, I thought it was like a very profound book. And I just like digested everything Morgan Housel published. And then a year after that, like, I remember when he followed me back on Twitter. I was flying from Sevilla, Spain to Manchester, England. I looked at my phone, I was like, oh, this is really cool. This is really cool. And then when I moved to New York, we like hung out in person at Collab Fund's office. And like, like, great guy, but I would say like as a somewhat career slash, just aspirational. Him and Tim Urban were like my two favorite bloggers from the kind of

[Barry Ritholtz]

like you referenced Tim Urban in the book, but I think you referenced a piece of his and I was surprised you didn't reference the piece on optionality, the sort of chart with the black lines.

[Jack Raines]

Everybody steals it on Twitter.

[Barry Ritholtz]

I find that piece to be so interesting because, you know, one of the things about getting old is some of your optionality goes away because you don't have, hey, this is a 25 year project. Do I really have 25 years? Like, what am I going to be doing at age 90? All right, maybe a 25 year project isn't the best thing for me or at age 80, best thing for me to start. But I laughed at a lot of your references because I'm familiar with many of them. They're really, really good. So you mentioned Morgan. Any other post college mentors you want to bring up?

[Jack Raines]

Yeah, I mean, I'd say my current boss, Sam Lesson, great guy. I mean, he's had a very cool career, right? He started a company in his 20s in Brooklyn, ends up getting acquired by Facebook, had a successful career at Facebook, and then co founded the venture fund I work at now. Like, he's like, it's, it's funny. I feel like a lot of people in my bubble of like the late 20s have this, like, is this what I want to do with my career? You kind of hit this inflection point of like, you should pick a thing that starts compounding and like his take has always been like, you should just want to work with like really interesting, smart people you respect and like work on interesting problems. And that's a pretty good recipe for finding career fulfillment. And you know, if a couple of things go right, like financial success, but like, it's, I don't know, he's done like a few different things and now like has like objectively, like, if my lifestyle and like life is set up kind of like His in my 40s, I'd be very cool with that. Like, he crushes.

[Barry Ritholtz]

So you mentioned Morgan's books. Tell us what you're reading now. What are some of your favorites?

[Jack Raines]

So I just started reading this book called 1873. I think it Came out pretty.

[Bloomberg News Host]

Ahmed.

[Jack Raines]

Yes.

[Barry Ritholtz]

Who won the Pulitzer for I forgot the name of the Four Central bankers that his first book was about.

[Jack Raines]

Yeah.

[Barry Ritholtz]

That is literally at the top of my queue. Ready to go. It's. How are you liking it?

[Jack Raines]

It's. I'm about halfway through and it's. It's like very good and interesting. I mean the. The thing I've. I've done this from time to time. Like I hadn't read much over the last year while I was working on that.

[Barry Ritholtz]

Yeah. Killer writing is a killer.

[Bloomberg News Host]

Yeah.

[Jack Raines]

You've.

[Ryan Reynolds]

You.

[Jack Raines]

As someone who's written books, I had so underestimated. Like, I have much more respect for other authors after going through that. Exactly.

[Barry Ritholtz]

You read books. You can't blog. You can't. It just sucks up so much bandwidth.

[Vanguard Advertiser]

Yeah.

[Jack Raines]

It's like all your free time goes to that. But something I've always liked is I've always been a big biography guy or like certain moments or events in history, because you can get the chat, GPT, whatever. People can pull a story together in 300 pages of a thing is so fascinating. And with like 8, 1873, reading about the stock market speculation in the Vienna, Austria stock market in the 1870s and then you're just pattern matching that against what I saw with retail investing in 2020, 2021, you just see human behavior playing out cyclically 150 years ago is just really, really interesting in a totally different time and market and paradigm, but it's the exact same same thing.

[Barry Ritholtz]

Lords of Finance was his first book that won the. The Pulitzer. I'm excited about that book. Any other books you want to mention?

[Jack Raines]

The Infinity Machine, the one about the DeepMind founders. It was by Sebast. Sebastian Malabi, I think. Anyway, it's like as far as AI is now the thing everybody cares about. He did a really good job of like. Like how LLMs even became a thing in the first place and how like this just group of like British researchers who've been holed up in London the whole time kind of kickstarted this whole AI boom. And even though Sam Altman, Elon Musk, they aren't like main characters at all. You're getting these interesting anecdotes of how like OpenAI came together and how there was like a bit of a coup with an open AI and then Elon leaves it. It just did a really good job of framing like the current moment in time and how we got here. But those are like. I read both of those or been reading both of those in the last Month and a half. They're great.

[Barry Ritholtz]

Interesting. What about streaming? What are you watching or. Or listening to?

[Jack Raines]

Give us your favorite hilariously on the like. On the, on the podcast front. I don't have any shows I listen to regularly, but I will selectively if there's like a guest that I find interesting. For whatever reason I've like. It's everything from tuning into like, like Josh and Michael on the Compound of Friends or like Tim Ferriss's show or. Or some of Scott Galloway's stuff. It's. I'm so much of a. I have people who I think are good interviewers. I don't care about half the people they talk to, but occasionally they'll have someone where I really want to hear that because I think they'll pull out good questions like, I don't know, like Michael Lewis on Tim Ferriss really good episode or it's. There's nothing I listen to specifically streaming. I did like that movie Obsession. I thought it was phenomenal. It was the one that like went mega viral out of Indie film that went mega viral out of nowhere.

[Barry Ritholtz]

Who directed it?

[Jack Raines]

It's what. It's the. I can't think of the guy's name. He was. Got his start on YouTube. He does a lot of short form comedy, but it like blew up and it was the one about the guy who like breaks the stick to make the girl like he makes a wish that the girl falls in love with him and then she goes full psycho. Anyway, it went like nuclear on Twitter, Instagram, TikTok, whatever. Pretty good. Good horror film. Thriller. I liked it.

[Barry Ritholtz]

Final two questions. What sort of advice would you give to a recent college grad interested in a career in either writing, content creation or venture capital?

[Jack Raines]

So my, my take on all the career stuff for that is like I think it's really. I think that one of the higher leverage things you can do is just start a blog and put your thoughts out there. Even if you have five people reading it, 50 people reading it. I think that especially with AI becoming more and more of a thing, it's easy to like resumes are becoming increasingly meaningless, both from like the odds of somebody actually looking at your job application when you send it in cold or very low, and the ability to like lie. Like you can make 100 different resumes of LLMs based on the job you're applying to now versus when I was like when I was in college. You always tweak your cover letter or resume per job and it's pretty tedious to do that when you're doing it by hand. You can make a million at once. Right. So having some like like proof of your thoughts on thing or you've articulated ideas online that show how you think. I think carry a lot more. They've always been important but like stand out a lot more now with AI or if you like AI coding assistants are really good. Like anybody can access them to build stuff. So just having a point portfolio of like written work or stuff you've built online that shows that you took interest and initiative in a thing and like put yourself out there super useful. I mean my, my take on career stuff in general is like if you can go into investment banking or consulting right out of undergrad, it's still probably the right move just from like getting trained on how to work hard. People who work at Goldman from 22 to 24 are typically more competent than other people. And for all my stuff about like you should go take risk in your 20s. The caveat on that is like you should have a couple of prestige stamps first. Like Columbia Business School was a prestige stamp for me. I enjoyed it. I learned a lot. The main reason I went was like I went to a somewhat no name undergrad. It's not like I worked at a marquee firm out of undergrad. Like you want to get a couple of like I have like somebody's de risked me as an individual. Then you go take the shot that you want to. So like I, it's like have a collection of like independent work and thoughts like you can share like in real time. And then I think it's important to get one or two prestige steps before you go jump off and do your own thing.

[Barry Ritholtz]

And yet in the book you talk about what a, what a misfocus it is hyping on status and, and why that whole game is so challenging.

[Jack Raines]

So my, the status thing's so nuanced. I think that if you treat status as an ends to itself, you're going to be incredibly disappointed. I think if you treat status as a thing that like you can acquire and leverage to actually do an end. Yes, like if the trade is I'm going to go to an incredibly competitive school and spend two to four years working in some version of like Goldman, Blackstone, McKinsey, whatever and I can come out of that and do anything that's very much worth it. But you don't want to be the person who, who like 10 or 15 years into their career never really figured out their thing so kept chasing status as like a vanity project makes, makes A lot sense. It's like I say status as diminishing returns or like once you have enough of gets marginal. After that you're good.

[Barry Ritholtz]

And our final question. What do you know about the world of investing today? Might have been useful back when you were locked in your bedroom trading SPACs.

[Jack Raines]

I underestimated how much retail investing is like a permanent fixture in the market today. I think it compounds from like and this is all like public market stuff. But like pod shops trading quarter by quarter are like more and more of a thing. Passive investing is more and more of a thing. You could argue that true like like price setters being like fundamental long short funds or and like long only mutual funds are less of a thing. So it's created this thing where you have like, like a lot of like very short term trading on like whatever alternative data, quarter by quarter data and then you have a lot of passive stuff and then a really big active group is like retail investing is a thing like GameStop I thought was a one off fluke. It wasn't like open door, short squeeze out of nowhere. You're seeing like random companies will just pop off like 500% which makes it like. Dan Sondheim was on a podcast with the Collison brothers, the stripe founders a couple months ago. He was talking about how they changed like how they position their shorts now D1 capital. Because you just, you could be fundamentally right. But guess what? Fundamentals don't matter if the borrow rates through the roof and the stock like eight X's and you get blown up right? Like like ask the Gabe the Melvin Capital guy about fundamentals when his fund got blown up right. Like it. At the end of the day the only thing that matters is making money. And I, I really thought a lot of that was a 2020, 2021 thing. And it was Covid and people were at home. We're seeing so much stuff with like random speculative like nuclear reactor. Like a company OCLO went public through a spac. It was like a Sam Altman backed company. It was worth like $40 billion. I don't think they have a functional reactor yet.

[Barry Ritholtz]

Like are you suggesting that sites like Reddit, Wall street bets still carry the influence they used to or has that attenuated and it's spread out to different areas.

[Jack Raines]

I would argue that they almost carry more weight because I think that like really I think there's. This is pure speculation but I think that they're now increasingly thing that like call it like institutional traders, quant funds, whatever will like look at as a data source where if something spikes on one of these sites they'll play the momentum and like it makes these bubbles go even further than they used to. And everything happens so fast now because like the speed that information moves on the Internet is just instantaneous. That like a bubble that might take like months to build up and then collapse could happen within a week both ways. So it's just like the, the whole like Internet spread of information faster and faster. It's all a derivatives like retail investors getting in the market and then yapping about stuff online that's just never going to stop.

[Bloomberg News Host]

Right.

[Barry Ritholtz]

And it's so funny because everything old is new again. Back in the day of the Yahoo

[Jack Raines]

message board it's like the late 90s. Yeah, yeah.

[Barry Ritholtz]

Like I Omega and and that's what of stuff. Nothing has changed. It's just how much faster.

[Jack Raines]

And it's like zero commissions now. It's like the there's.

[Barry Ritholtz]

And it's in your pocket. You don't have oh let me go home and call my broker doesn't.

[Jack Raines]

And now there's like oh, we have prediction markets and sports betting on your phone. We have removed all friction from people putting money at risk to do stuff.

[Barry Ritholtz]

And we've made regardless of how dumb or speculative it might be and the

[Jack Raines]

speed at which you can communicate what you're doing is now also instantaneous and free. So you just have people constantly going risk on. On whatever for whatever reason and then everybody else knows it. That's just, that's only going to keep accelerating.

[Barry Ritholtz]

Except it kind of sounds like a very late stage bull market.

[Jack Raines]

Could have said that in 21 and we were right. 22 is kind of a bear market. Then I happened. So it's like I think that, I just think market cycles in general will keep happening faster and faster because it'll collapse. People get blown up and somebody starts running. Another thing, I just think it's going to get more and more violent.

[Barry Ritholtz]

I have a pet thesis that the giant reset, the giant fiscal stimulus and crash and recovery in 2020 was like a reset and extended the bull market. Another.

[Jack Raines]

I agree with that.

[Barry Ritholtz]

Ten years it's. But anyway, Jack, you. You were more than a somewhat special guest.

[Jack Raines]

Thanks.

[Barry Ritholtz]

This was really great. Thank you for being so generous with your time. We have been speaking with Jack Raines. He is the author of Young A Field Guide to Wealth and purpose in your 20s. If you enjoy this conversation. Well check out any of the 653 we've done over the previous 12 years. You can find those at iTunes, Spot, Spotify, YouTube, Bloomberg, or wherever you find your favorite podcasts. I would be remiss if I didn't thank the crack team that helps us put these conversations together each week. Alexis Noriega is my video producer. Sean Russo is my researcher. Anna Luke is my podcast producer. I'm Barry Britholtz. You've been listening to Masters in Business on Bloomberg Radio.

[Bloomberg News Host]

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[Barry Ritholtz]

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