Sparking Opportunity in Commerce with Michael Kassan: The Power of People, Legacy, and the 3 C's

Summary

Brave Commerce: Sparking Opportunity in Commerce with Michael Kassan Release Date: October 22, 2024

In this compelling episode of Brave Commerce, hosts Rachel Tipograph, Founder & CEO of MikMak, and Sarah Hofstetter, President of Profitero, sit down with Michael Kassan, the visionary Founder and CEO of 3C Ventures. Kassan delves deep into his entrepreneurial journey, the foundational importance of people in business, his strategic framework—the "3 C's," and his aspirations for his legacy in the eCommerce and venture capital landscape.

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Introduction to Michael Kassan and 3C Ventures

Michael Kassan begins by sharing the genesis of 3C Ventures, an enterprise built on the pillars of Consulting, Convening, and Co-Investing. These three elements, collectively known as the "3 C's," form the backbone of his strategic approach to fostering innovation and growth within the eCommerce sector.

Michael Kassan [05:15]: "It's descriptive in my view of what I was going to be focusing on: consulting, convening, and co-investing."

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The Paramount Importance of People and Talent

A central theme of the conversation revolves around the critical role that people and talent play in the success of any organization. Sarah emphasizes the challenges of hiring, training, and retaining top talent, a sentiment echoed by Rachel.

Sarah Hofstatter [02:12]: "People. Talent. No question. You got a better answer? No."

Kassan concurs, highlighting his own experiences in building teams and the intricate process of identifying individuals who bring that indispensable "spark."

Michael Kassan [14:58]: "There's always that spark, Sarah... It's amorphous, but when you see it, you know."

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Building Legacy Through the 3 C's

The discussion shifts to Kassan's vision for his legacy. He aspires to be remembered as a "mensch"—a person of integrity and honor—who significantly contributed to the industry. Kassan reflects on how his past experiences have shaped his current endeavors and future aspirations.

Michael Kassan [09:21]: "I would like that to be the legacy, obviously with the substantive underpinnings of that."

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Learning from Regrets and the Importance of Due Diligence

Kassan openly discusses his regrets, particularly a recent transaction that did not yield the expected outcomes. This candid reflection underscores the importance of due diligence, especially when evaluating potential investments and partnerships.

Michael Kassan [10:20]: "I made a bad judgment and it's one that cost me, and I'm sad about that."

He advises founders and operators to ensure that promises are backed by capable people and to thoroughly vet the individuals involved.

Michael Kassan [13:05]: "Make sure that the promise is backed up by the people and make sure you do the proper diligence on the people."

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Hiring Philosophy: Seeking the Spark

Kassan elaborates on his unique approach to hiring, seeking individuals who exhibit a certain intangible quality—the "je ne sais quoi." He shares an anecdote about hiring Grant Gitlin, whose insightful question during an interview revealed his exceptional potential.

Michael Kassan [14:58]: "...something about that question sparked something in my mind... You see, I don't know what it is. I don't know how to describe it. It's amorphous. But when you see it, you know."

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The T's and C's Framework: Navigating Industry Trends

To articulate his focus areas, Kassan introduces the T's and C's framework:

• T's: Trust, Transparency, Talent, Technology, Transformation
• C's: Content, Commerce, Culture, Creativity, Community, Curation

This structured approach allows Kassan and his team at 3C Ventures to navigate the complex and ever-evolving landscape of eCommerce effectively.

Michael Kassan [19:00]: "Trust, transparency, talent, technology, and transformation... Content, commerce, culture, creativity, community, and curation."

---

Connector and Maven: Leveraging Industry Connections

Kassan discusses his reputation as a connector and maven within the industry. He emphasizes that while having an extensive network is advantageous, the true value lies in how one leverages these connections to drive meaningful collaborations and innovations.

Michael Kassan [17:21]: "It's what you do with it and how you understand it and how you navigate it."

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Reflections on AI and Industry Dynamics

The conversation takes a light-hearted turn as Kassan humorously references the pervasive role of AI in contemporary discussions, even making its way into synagogue sermons.

Michael Kassan [20:52]: "The drinking game is on. It's continuing in the rabbinic universe."

This anecdote underscores the ubiquitous nature of technological advancements and their integration into all facets of life and business.

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Final Insights and Legacy Aspirations

In the closing segments, Kassan shares a poignant personal reflection about his bravest and smartest decision—parenting his children and grandchildren, symbolized through the celebration of their bat and bar mitzvahs.

Michael Kassan [22:04]: "That's the bravest and smartest thing I did. But the luckiest thing I did as well because of the dividends, that's the children and the grandchildren."

He reiterates his commitment to leaving a meaningful legacy both professionally and personally.

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Conclusion

This episode of Brave Commerce offers a deep dive into Michael Kassan's strategic mindset, emphasizing the pivotal role of people, the importance of strategic focus through the 3 C's and T's and C's frameworks, and the value of building a legacy grounded in integrity and meaningful contributions to the industry. Kassan's candid reflections and seasoned insights provide invaluable lessons for entrepreneurs and marketers navigating the dynamic world of eCommerce.

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Notable Quotes

• Michael Kassan [05:15]: "It's descriptive in my view of what I was going to be focusing on: consulting, convening, and co-investing."
• Sarah Hofstatter [02:12]: "People. Talent. No question. You got a better answer? No."
• Michael Kassan [14:58]: "There's always that spark, Sarah... It's amorphous, but when you see it, you know."
• Michael Kassan [09:21]: "I would like that to be the legacy, obviously with the substantive underpinnings of that."
• Michael Kassan [13:05]: "Make sure that the promise is backed up by the people and make sure you do the proper diligence on the people."
• Michael Kassan [19:00]: "Trust, transparency, talent, technology, and transformation... Content, commerce, culture, creativity, community, and curation."
• Michael Kassan [20:52]: "The drinking game is on. It's continuing in the rabbinic universe."
• Michael Kassan [22:04]: "That's the bravest and smartest thing I did. But the luckiest thing I did as well because of the dividends, that's the children and the grandchildren."

---

For more insightful conversations and industry-leading perspectives, tune into Brave Commerce on your preferred podcast platform.

Transcript

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[Michael Kassin]

The nuance within Consulting the nuance within Convening the nuance within co investing would be much too long for this podcast for this conversation, but let it suffice to say that As I said 18 years ago, I had an opportunity to peer around a corner and see the opportunity and look at the plot of real estate, at what I characterized as the intersection of marketing, media, advertising, entertainment, sports and technology. And I found a plot of real estate there. And it was uninhabited. And that old joke we have all heard in our life, look to your left, look to your right. I did. There was nobody there, so I took the spot.

[Sarah Hofstadter]

Welcome to today's episode of Brave Commerce.

[Rachel Tippograph]

I'm Rachel Tippograph, the founder and CEO of Micmac.

[Sarah Hofstadter]

I'm Sarah Hofstadter, president of Profitero, and.

[Rachel Tippograph]

This is a show that talks about what's relevant in E commerce for the world's biggest brand brands. Sarah, what do you think is the most important asset that any company has?

[Sarah Hofstadter]

People. Talent. No question. You got a better answer? No.

[Rachel Tippograph]

Human capital, absolutely. But what comes with that is your ability to hire, correctly, train, retain. And to be perfectly honest, I have found it to be the hardest part of the job.

[Sarah Hofstadter]

I would say as well, being able to read somebody in a 45 minute interview process and doing that over and over and over again and doing it with your most junior and most senior employees. It's just. It's hard to be able to find that je ne sais quoi, whether that's hiring your talent or even finding people to work with. Think about how much you and I have done together. It sparked from a dinner where we just clicked, but that was many hours together and then multiple conversations that kind of get there. You still have to figure out, what's that spark? What's that kernel that gets you there. I remember the first time I met Michael Kasson. Yeah, it was in a conference room at 360i's early days. It was him and Wenda Millard. They had just started medialink. They were looking at the right kind of companies, both to invest in as well as to bring clients in and whatnot. And I didn't know about his reputation. I didn't know the whole Michael Kassen story. I was just relatively new to the industry. And you walk in and you know, that's somebody with the spark. It's not the name dropping. It's the understanding of when and where and how to be at the intersection. He and Wenda took an early stake in 360i before it was sold.

[Rachel Tippograph]

I've never looked into 360i's investors.

[Sarah Hofstadter]

Well, we sold the company 14 years ago, something like that. So. But this was early. This might have been like 2005 when we first met Michael and Wenza. And we can have a whole episode on the buying and selling of 360i. But he's got a lot of story. He's got a lot more stories of Mr. Kassin, some of which he has shared with us today.

[Rachel Tippograph]

Well, I have an employee at mcmac who grew up at medialink, and he is a star employee. So I really think that he does know how to pick talent. Who better to hear from on how to do it than Michael Kasson himself? So let's bring him onto the show.

[Sarah Hofstadter]

Michael Kassin, founder and CEO of 3C Ventures. We are thrilled to have you on the podcast. Thanks so much for joining us, Michael.

[Michael Kassin]

Well, Sarah and Rachel, it's a pleasure. Two people that I have great respect for. And if there's anything that I like to do, it's talk. So this is fun for me.

[Sarah Hofstadter]

Actually, I think you're a better listener than you are talker, and you're a pretty damn good talker. So let's get into it.

[Michael Kassin]

I'll tell you a story. I'm funny about these old lessons that I learned when I was young. My grandmother taught me a few, but one that she taught Me was, there's a reason you have two ears and one mouth. You should listen more than you talk.

[Sarah Hofstadter]

So it's clear that you've taken that to heart. I think my softa taught me that as well. I don't know how much I listened. Yeah, that's another story.

[Michael Kassin]

My grandmother also taught me another one, which I use a lot, and you've probably heard me use it over the years. Sarah. It was don't read people's lips, watch their feet. Don't listen to what people say, Watch what they do.

[Sarah Hofstadter]

I like that.

[Michael Kassin]

Yeah.

[Sarah Hofstadter]

Let's get into the newest information, which is you starting Three Seasons Ventures. So can you just ground everybody? What is it? And the podcast is called Brave Commerce. So if there's a commerce angle, you have bonus points.

[Michael Kassin]

Right. So as I was contemplating what's next, a tough decision for me to leave the company that I founded. Those things are tough because I'm an emotional kind of guy. And I look at from whence I came, and I think, you can't ever forget that. As we're approaching on the calendar from whence I came, what I grew up calling Columbus Day, which is now Indigenous People Day, from whence I came was from Brooklyn 71 years ago when we moved to California on what is now Indigenous People Day. So I look at from whence I came, geographically in the one case. But what I look at it professionally. I had the good fortune 18 years ago, roughly, to look around the corner and come up with the idea for my previous company. And I'm very proud of what I was able to build and the people I was able to attract and the kind of ripple I was able to have in the pond, if you will, of our industry with my previous company. So when I looked at this opportunity, I said, what am I going to do and what do I want to focus on? And I was sitting with a good friend of mine named John Miller, who many of you may know who industry Boldface name, having been around for a long time back in the day ran AOL and then News Corp, Digital Leadership and many, many other important plays in the industry. And we were sitting around in the spring, and he said, so, Michael, what do you want to do next? What are you going to do? And he took a piece of paper, and it was a proverbial whiteboard. We were at a table. So it wasn't actually a whiteboard, but it was a table that you could write on the tablecloth. So he said, so you're going to consult. So he writes the word consult. I said, yes. He said, and you're still going to do your events and you know, what you've done with the industry, with CAN and CES and Possible and all the different events. And he says, so you're going to convene. So he writes the word convene. And he says, I presume you're going to still through a family office lens and invest in things. And I said, yes. He said, so you're going to co invest. So here's a piece of paper sitting in front of me that says consult, convene and co invest. And I said, so it's the three Cs. That's how I got to three C. So it's not some mysterious, you know, story as to what it means. It was descriptive in my view of what I was going to be focusing on, consulting, convening and co investing. And I think that's a good way to describe the what and, you know, the nuance within consulting. The nuance within convening, the nuance within co investing would be much too long for this podcast, for this conversation. But let it suffice to say that, As I said, 18 years ago, I had an opportunity to peer around a corner and see the opportunity and look at the plot of real estate, at what I characterized as the intersection of marketing, media, advertising, entertainment, sports and technology. And I found a plot of real estate there, and it was uninhabited. And that old joke we've all heard in our life, look to your left, look to your right. I did. There was nobody there, so I took the spot. I have the opportunity again, Rachel and Sarah, to look around the corner. The only difference is even though I've gotten older, my eyesight's actually gotten better because I've had the experience of the things that I did and now don't want to necessarily do the same or the things that I didn't do that I want to now add in. So that's the moment that I'm at right now. I've peered around the corner. That plot of real estate is still there. There's other people around that plot of real estate. But I think I have a unique opportunity to capitalize on my experience and the connectivity and the imagination that I have around where this industry is going at this point, number one. But I have a little more. But let me take a breath because that was a long winded answer.

[Rachel Tippograph]

So playing this out 10 years from now, after you've accomplished the three Cs, what do you want the industry to say about you? What's your legacy with the three C's.

[Michael Kassin]

Whoa. That's a good question. And I'm a believer that legacy matters. But I guess the legacy that we all want is that the industry would look at me and say I was a good person and that I contributed to the industry and I saw opportunity for the industry and I tried to capitalize on that for the industry, but obviously for myself as well. Yeah, I think, number one, always, as we would say, a mensch. Okay. And I'd like that to be the legacy, obviously with the substantive underpinnings of that. But yeah, I think I would probably be very happy if that was the industry moniker that I could walk away with.

[Sarah Hofstadter]

So as we get a little nostalgic, I guess, are there any, like, leadership decisions that you regret? In hindsight, I have no doubt you will leave a Menschla mark. You already have and will continue to do so on the flip of it. Decisions you've regretted and perhaps has shaped the way you think about navigating.

[Michael Kassin]

Yeah, the last transaction that I completed, which didn't end well, is probably the biggest regret that I have because I'll be honest, because I am. I never expected to carry a different business card. I regret that transaction very, very seriously. I made a bad judgment and it's one that cost me, and I'm sad about that. So, yeah, the promise of that transaction on paper was real. The substance of it wasn't. And so, yeah, I would say that's probably in business, one of the decisions I regret the most. However, in the spiritual nature of our conversation, I also was taught, like you, when God closes a door, God opens a window. Or the other way around. So, yeah, this door closed unexpectedly. You know, my choice, but still unexpectedly. But the window that's open is very exciting to me.

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[Michael Kassin]

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[Sarah Hofstadter]

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[Rachel Tippograph]

Michael, as a fellow entrepreneur who hopefully a story like yours when you're doing diligence on the next stage of your company, what learnings do you have for operators and founders as they evaluate those possibilities?

[Michael Kassin]

Yeah, make sure that the promise is backed up by the people and make sure you do the proper diligence on the people. You know, I was on the phone with the chief Marketing Officer this morning asking me career advice. And I said, this is an analogy, but it's a good example, I think. At the Forbes CMO conference a couple of years ago, Seth Matlins was interviewing me and he said, michael, and it was a very provocative question. He said, michael, what does the CEO generally not know about the role of the cmo? And I thought that was such a brilliant question because it brings into question so many elements of what I think helps me answer your question. I said, well, that's, you know, it's interesting because I think it goes back to the job description. So what I've used that provocative question for is a great piece of new business. Always you ask that question to a CEO and you're going to get so many answers and you're going to make the CEO think about it. And I've done that frequently because I then say, well, look, it goes to the job description in the title. If you give somebody a job description of chief growth and marketing officer, does that person have the levers that they need to execute growth? That's where I'm going to go with this. So the diligence is make sure that what you write on a piece of paper in terms of integration and in terms of, you know, systems and in terms of all of that is backed up by the people that you actually have the levers. The levers would be the people.

[Sarah Hofstadter]

So with that in mind, I mean, you are de facto the most connected person in our industry. And no matter which one of the words or alliterations you use that would be to define our industry, you would still be the most connected, whichever one we were looking at. You're connected to a lot of power. And you talk about betting on people. What's your filter for how you think about, like, okay, I'm going to bet on this person. Maybe he or she is not in the inner circle at this point, but I see something. What is that? Je ne sais quoi.

[Michael Kassin]

There's always that spark, Sarah, and that's hard to put into words. It's lightning in a jar. You know, I tell the story of when I hired Grant Gitlin to be the first chief of staff, and I made up the title. And Grant was such a unique individual. He was there to interview. It was early in my previous company, and he was there for an associate job. And in the meeting, he asked me a question. He said, michael. And I'm paraphrasing because he would never have asked the question in these words, but I'm paraphrasing. He said, michael, would it be interesting for you to meet the young, hip digiratai in New York? And again, he did not say that I'm paraphrasing. I said, so are you asking me if I would want to meet Mark Zuckerberg before he was Mark Zuckerberg? And he said, yeah. I said, is that a blonde joke? Okay. I mean, I was being sarcastic. I love blondes. No kidding. But I was being sarcastic. It's kind of like, is that an IQ test? I mean, of course I would like to. Something about that question sparked something in my mind, and at that moment, I riffed on a job description of what became chief of stuff. And I had not thought about it one moment before that conversation. And I said to him, let me ask you a question. Would you be interested in this role? And I literally articulated the role in a riff. And when I finished reminding you, I asked it as a question. He looked at me and said, is that a blonde joke? And I said, you're hired. Okay. There was a spark. I saw it. How do you put that into words? Well, I did, but it's anecdotal. There's something. You see, I don't know what it is. I don't know how to describe it. It's amorphous. But when you see it, you know.

[Rachel Tippograph]

It'S just real quick, we have a shared mutual. I had coffee with Linda Boff this morning, and she brought up Grant. So, Grant, I hope your Ears are ringing.

[Michael Kassin]

He texted me last night, and I owe him a phone call. But, you know, I tell you this. Nellie Boff, Linda's daughter, was one of our mentees and, you know, interned and then worked at medialink for a very long time, so. And I have a big heart for Linda, both and the entire family, so.

[Sarah Hofstadter]

Talk about making bets. I mean, Michael, you and I met when you took an early investment in 360i. About 20 years ago. Something like that. There's something about that where you seem to be in the right place at the right time. Like, all the freaking time, you're saying it's that?

[Michael Kassin]

Well, but you know what, Sarah? Being in the right place at the right time, you have to know it.

[Sarah Hofstadter]

Yeah.

[Michael Kassin]

There was a great degree of insecurity for me early in this iteration of my career, when at the beginning of the century, people would introduce me at events and I'd speak, and they'd go, michael Kasson with the biggest Rolodex in the world. And I would be pretty insecure about that because I'd think, whoa. I think I've accomplished a few things in my life. I went to college, I went to law school, I went to graduate school. I built a couple of businesses. I've had some good fortune. And I thought, is that what I've achieved? I've achieved notoriety because of a Rolodex. The insecurity went away when I realized, it's great to have this. Okay. But it's what you do with it and how you understand it and how you navigate it. That was the special sauce that I think I brought. So my insecurity went away because I went, actually, it's a compliment.

[Sarah Hofstadter]

I certainly think it is. And especially again, it's how you use it. That's the difference between being the maven and being the connector. And I actually think you're both. To be a good connector, you need to be a maven, and to be a good maven, you need to have the right connections.

[Michael Kassin]

Well, it's worked out. Look, let me not answer a question that hasn't been asked. But going back to the words, and words matter, I identified the themes that I want to focus on in 3C, and it came back to words. About two years ago, I stumbled on something where I was asked in the role that I somehow have in this industry, and I'm going to harken back to a curb your enthusiasm episode. One of my favorites was about a dinner party, and Larry David was trying to figure out who was going to be the Middle at the dinner party.

[Rachel Tippograph]

The middler.

[Michael Kassin]

The middler, okay. I kind of think I somehow either self anointed or appointed as the middler in the industry. As such, I had to come up with the words or phrases that I would use to spark the conversation. Because if you're in that role, you got to know, what am I going to say at that dinner party, proverbially to start the conversation. So I wrote down a bunch of words and it turned out that the word started with either the letter T or the letter C. So I said I'm going to adopt these as my T's and C's. I don't mean terms and conditions. But if I have to shine a light on the areas that I want to focus on, I'm going to let the T's and C's guide me. So here you go. The T's and what I mean by this are the industry focus areas that I think we all are dealing with. The T's are trust, transparency, talent, technology and transformation. I haven't met anybody lately that's not in some sort of a transformation. Trust, obvious. Transparency, critical talent, the dearth of talent and technology, kind of duh. Obviously those are the T's, the C's. This is a gift to you, Sarah, in the profiteero part of your life, which is the C words. Content, commerce, culture, creativity, community, curation. Those are the C words. And I start with content and commerce because it's rare lately to hear the word commerce not being modified by the word content in that context, another C word, I look at it and say, if I have to tell you where 3C is going to focus, it's going to focus on those words and the manifestations of those words in practice. Trust, transparency, talent, technology and transformation. Content, commerce, culture, creativity, community and curation. I rest my case.

[Rachel Tippograph]

Maybe the ampersand is AI.

[Michael Kassin]

There you go. It's the word. Rachel, when the interweb was getting started and you'd be at a cocktail party and everyone would say, hey, do you have a website? Oh, do you have a. Oh, we need a website. I mean, I'm going back a long time today. It's, you know, the drinking game in our world is AI. By the way, I told this story publicly a while ago and it's exactly a year ago. Lynn Lewis, somebody. I'm sure we all know in the industry we had kitted around in the summer of 23 that AI was the drinking game because every conversation you had AI came up. We're sitting in temple last year now, literally a year ago in Rosh Hashanah, and I get a text from Lynn Lewis, obviously reformed temple, or she wouldn't be texting during temple, but kidding. But I get a text and says, well, the drinking game has continued. My rabbi just mention AI in his sermon. Not two hours later because of time zones in my temple, my rabbi mentions AI in his sermon. I sent Lynn Lewis back a note. I said, the drinking game is on. It's continuing in the rabbinic universe.

[Rachel Tippograph]

Well, Michael, we could literally pick your brain for decades, but we gotta ask you our famous last question, which is, what's the bravest thing you've ever done?

[Michael Kassin]

Well, I'm gonna change it to say the smartest thing I ever did, because it's the same 50 years ago. Ronnie this.

[Sarah Hofstadter]

Ronnie.

[Michael Kassin]

Yes. Wow.

[Rachel Tippograph]

Mazel dub.

[Sarah Hofstadter]

It all comes back to Ronnie. Nothing happens in a conversation without Ronnie.

[Michael Kassin]

Absolutely.

[Rachel Tippograph]

That's amazing.

[Michael Kassin]

And this December is 50 years. Well, that's it. And by the way, that was the bravest and smartest thing I did. But the luckiest thing I did as well because of the dividends, that's the children and the grandchildren.

[Sarah Hofstadter]

Oh, you should continue to have. I feel like I'm already in shul. You should continue to have nachos from your children and grandchildren.

[Michael Kassin]

You know this, I think. But literally, in the month of September, we had a bat mitzvah and a bar mitzvah one week apart.

[Sarah Hofstadter]

So beautiful.

[Michael Kassin]

I put on a suit this month more than I wanted to.

[Sarah Hofstadter]

Better for the simcha than the other one you put on the suit.

[Michael Kassin]

Exactly.

[Sarah Hofstadter]

Well, Michael, thank you so much for joining us on Brave Commerce. We can't wait to see all the awesomeness that 3C has in store. And maybe we'll even be invited to a party.

[Michael Kassin]

You know you will. Rachel and Sarah, I want to thank both of you. Appreciate it. And as I said at the beginning, I love to talk. So thanks for the opportunity.

[Sarah Hofstadter]

Truly an opportunity for everybody to use their ears and listen. So thank you.

[Rachel Tippograph]

Thank you if you enjoyed hearing from one of our industry greats. We've had many on the show, but two in particular that are part of Michael's orbits that we want to highlight. Go check out an episode that we did with Shelly Zalas or go check out a very early episode with Gary Vaynerchuk. If you like what you hear, write a review, tell a friend. Share on LinkedIn. Thanks for listening.

[Jackie Cooper]

Gifting is hard, but here's a hint. Give the gift of connection from US Cellular. Not sure what that means. Well, here's a slightly more specific hint. You can choose four free phones and get four lines for $90 a month from US Cellular. Your family wants new phones? How do we know? Well, they told us. The good news is that compared to wrapping presents, you're great at getting hints. So take the hint and get them four free phones in four lines for $90 a month. US Cellular built for us.

Hi, I'm Jackie Cooper, Global Chief Brand Officer at Edelman and the host of Touch of Truth, a new podcast launching on the Adweek Podcast Podcast Network. My dad gave me this incredibly smart piece of advice. Meet everyone once. As a result, I've met some of the most fascinating and inspiring people on the planet. Now on Touch of Truth, we're coming center stage and sharing the mic to experience stories of truth, insights and visions for the future that will challenge your way of thinking. Touch of Truth is available wherever you listen to podcasts. New episodes come out every Tuesday. I do hope to see you there.