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Travis (Podcast Host)
I oh, let's go. I oh, let's go.
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Travis (Podcast Host)
What's going on, everybody? Welcome back to the show. On this episode, it's just me, you and the mic and we're continuing along our series of talking about some of the lessons and takeaways I've had from previous previous guests here on the show. Of course, you can go check out all the full interviews with each and every one of these people and I highly recommend doing that if you liked what we talk about in these. Today's episode is all about my time with my buddy, Jeff Fenster. Jeff is a serial entrepreneur. And I mean that in the true sense of the word. Some people, you know, they, they build something and then they go build something else that's very similar to that last thing and then they build something else that's very similar to the last two things. I'm not saying that that doesn't make them a real entrepreneur. That's not at all what I'm saying. It's just that a lot of people use the word serial. But what's interesting to me about Jeff's journey is that he, his first version of a company was like a, a payroll software company, like an ADP competitor, which he built and then sold. His next iteration of a business was a agency that he built with Neil Patel, who's one of the, one of the smartest digital marketers out there, I think, and then sold that and then got out of that. And then in his words, his, his wife got fed up with him being at home all the time. I was basically like, you need to find something to like to, to do to, to be busy with. And so he started this acai bowl company called Everbowl. And if you think that sounds familiar, it's because my wife and I actually own an Ever bowl franchise. So Jeff is the founder of, of Everbowl. They have now over a hundred locations and, and they have done an amazing job at vertically integrating each part of the distribution process and owning the entire workflow so that they could actually build a really profitable business in this space. Because franchises themselves are not crazy profitable, believe it or not, even when they have this many locations. So lots of great memories from my time with Jeff because we've spent a lot of time together now at this point, but also from this conversation, lots of great takeaways as well. So let's go ahead and dive in. Number one, when you have a problem, stop before you solve it and look for a different angle. So Jeff became the number one sales rep at ADP in his first six months, which is crazy, cause ADP is a massive company and they have a very in depth sales training program with a lot of really good salespeople. So became number one in six months, not by doing more cold calls, but by stopping and asking, who else needs what I'm selling and how can they come to me instead? So instead of just cold calling random businesses, he found bankers, accountants, insurance agents, bookkeepers, people who were seeing brand new business owners every single day. And he built relationships with those people. And then those people became his referral pipeline. So he went from cold caller to order taker. The formula was right in front of every ADP rep, but no one stopped to question it. Jeff paused, evaluated the actual problem, and then went around the problem and figured out another solution to it. And then became the number one sales rep in ADP in six months. Again, pretty crazy considering the extent of that sales organization. And it reminds me, another friend of mine, guy by the name of John Rulin, Rest in peace. John died suddenly and tragically a couple couple years ago now, which is crazy. But John. John was a really, really good dude. He wrote a book called Giftology. Kind of became the gifting expert because he was a Cutco rep, which is also a massive sales organization. And they had their own systems and trained everybody the same way. And then he came in, was like, I wonder if I could do it like this. And so instead of just selling knife sets to homeowners, he started building relationships with real estate agents and basically would sell a set of knives to the agent, and then the agent would use them as gifts for their clients once their client got into a new home. And so he started doing that. He became the number one sales rep in all of Cutco by a long shot. And literally changed their entire training program internally because they were like, holy shit, this dude's selling so many knives doing something that we didn't tell him to do. What is he doing? So he came in, started training a lot of Cutco reps and then, and then ended up building this, this company for basically corporate gifting. So they had a ton of different clients from all types of, of corporate companies and they basically just paid them on a retainer to identify their top, their upper echelon of clients, like the top 20% of the clients that paid them the most money throughout the year. And then they would send them gifts like every quarter or once every six months or something like. So he became the gifting expert. And if you are in a space like that and you have high value clients, I highly recommend reading John's book by the way, Giftology because it gives you a framework, you know, the do's and don'ts of giving gifts, of giving good corporate gifts. And I followed that framework ever since and it's actually been really helpful for me. So anyway, that's a different conversation when we're talking about what Jeff did here and what John did. It's you, you if you have find yourself coming up against the problem before you just like use the solution that everybody's using, look for a different angle. You sometimes that ignorance can be really helpful. It's just like everybody else is doing this thing because that's just how it's always been done. That's just what we've been trained to do, which is never a good reason to continue doing something. So there's a better way then try the better way, look for a different angle, be unique, be different, stand out. Number two, which would you rather is the most honest decision framework you'll ever use? This is a tool Jeff calls out explicitly and it's one that I'm going to use myself. Whenever you're at a crossroads, whether to quit, whether to pivot, whether to take a risk, play out both worst case scenarios, not both best case scenarios. Worst case, start your own business, it fails and you go back to your day job. Worst case, you stay safe, but you're miserable for the next 20 years. So it's like you're coming up against a big decision. And instead of saying like what's the best case here on both of these, you try to allow yourself to go to the worst case scenario. And once you compare the real downsides instead of the imaginary upsides, the right move usually becomes clear. And this is what Jeff used to walk away from his six figure job at 24 with all a wife and a kid and six figures in law school debt and start his own business for the first time. It was just like which, which would you rather have? Which worst case Scenario, Would you rather have, Would you rather have this worst case scenario or this worst case scenario? And I find this to be really helpful because oftentimes the worst case scenario is not that bad. It's just that we build it up to be that bad. It's like, well, what if I fail? It's like, okay, well, let's play that out. Let's imagine you fail. What's going to happen if you fail? And for most people, again, there's extenuating circumstances and other people who don't have, you know, the privileges or blessings of maybe having family they can fall back on or a parent who can help them out or a friend's couch they can sleep on. I understand that there's some situations like that, but for the most part, the worst case scenario is really not that bad. Like, the worst case scenario is like, oh, I go try this thing for a year, didn't work out. All right, well, let me just go back to get another corporate job. Let me just like settle back into this other thing that I know how to do, and then I'll take another shot in another year or two when more financially stable or something like that. You'll just find if you do this exercise, I think that the worst case scenario is typically not as bad as you're thinking it's going to be. And try to look at the worst case scenario through your lenses versus the lens of culture and society and what the expectations of them might be on you. Because I think that's a mistake that people make where they're like, oh, worst case scenario is I'm going to fail. And then all my classmates from college are going to be secretly pointing and laughing at me because I can't afford to eat at the fancy restaurant that they're eating at because they stuck it out on, you know, on Wall street and now they're making 200 grand when they're 30. And I tried this business that failed and I'm, you know, scraping pennies together and eating peanut butter and jelly sandwiches and whatever. So it's, it's, it's worst case scenario for you. Like, to me, that was never a bad case scenario, like eating BB&J. You know, I was just always willing to be like, oh, well, you know, if my lifestyle goes down, my lifestyle goes down. What, Whatever. Like, I've been there before. It's not, it's just not a big deal. And you're probably ranking the worst case scenari on the, on the list of things to be wary of. So I like this frame a lot that Jeff called out, and I use that frame a lot.
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Travis (Podcast Host)
Number three, the golden rule of fundraising. He who has the gold makes the rules. Which you will remember from the movie, the classic film Aladdin. Jeff and his partner built a payroll company, took on private equity, got diluted round after round while the private equity firm kept putting in more money in exchange for more equity until they owned so little that what the company sold, Jeff barely made what the experience was worth. He said, you know, they were, there were 2425 year olds willing to work 2200 hour work weeks. The PE firm was smart enough to recognize that the lesson, understand your cap table before you take investment capital, understand the terms before you sign. And never, ever, ever, never assume goodwill from people whose job it is to maximize return on capital. You can't be surprised. Like, you know, it's the. They walk like a talk, walk like a duck, talk like a duck, move like a duck, they're probably a duck. It's like this same thing, like venture capitalist, private equity. Like, they have their metrics, they have their, their go. And don't be surprised when they act the way that they are supposed to act. Just understand the cap table, understand the investment capital, understand the terms before you sign. Because money is not everything and it will not solve all of your problems. And sometimes it actually injects more problems into the situation. So Jeff has now raised tens of millions of dollars for different companies that he's ran. And I like this bit of fundraising advice that he gave us. Number four, solve your own problem and you might accidentally build a business. Jeff couldn't afford to build out every Ever bowl location when he first started. So he started Ever bowl in San Diego County North North County, I believe. And it was about 300,000 a pop to build out every Everbowl location. He couldn't afford to just continue expanding ad nauseam because it was too expensive to build the location. So what he ended up doing is he built a prefabricated construction company that he called We Build. And We Build became the contractor that started building out all of the Everbowl locations. So he vert vertically integrated the construction process into his expansion with the restaurants so that it would be cheaper for him to be able to move from store to store from location location and not lose valuable time and money. And then We Build became its own spun out construction company. So now they have We Build Forever franchisees specifically who built out our location. But they also have We Build Global which now assembles entire restaurants in seven days and has landed clients like Shaquille o' Neal's Big Chicken and several other massive franchise concepts. He wasn't, he wasn't, you know, he didn't start Everbolt to destroy, to disrupt the construction industry. He was just trying to scale his own franchise. He was trying to scale his own company better and save the on the buildout costs. But solving that problem really well created an entirely separate, massively scalable company. And where a lot of the profits in the Everal Corporation actually come from are the construction arm, not necessarily even the, the food arm. And so he draws the parallel to Slack, which started as an internal communication tool for a gaming company that just wasn't working. And so the side solution that they built to solve the internal communication for them at this, this gaming company ended up becoming this, you know, juggernaut of an enterprise software company called Slack, which everybody's heard of now. So the side solution almost became like, becomes the main event. So solve your own problem and you might accidentally build a business, which is a really good rule of thumb for anything that you come across. Not just like, oh, we built a business and what else can we do to cover costs, whatever. But if you're just starting a business from scratch, you know, solve your own problem and you might accidentally build, you might accidentally build a business. If you're coming up against a problem, you can't find a solution. It's probably a sign that there's a lot of other people out there who could use a solution to the problem as well. So if you build that solution and it ends up working for you, then it might be something you could turn around and sell to other people. So solve your own problem. You might accidentally, you might accidentally build a business. Number five relationship capital compounds and it gets you meetings that you know don't make sense. It gets you, get you meetings that sometimes you find yourself in that you're like, how am I even here? Like, how do I even deserve to be in this room? And so when after Jeff sold the payroll company and he wanted to partner with Neil Patel, he didn't ask for a meeting with Neil and then pitch an idea. He sold a six figure digital marketing contract first, then called Neil and said, hey, I have a check for you. Where do I send it? That's it. So, so Neil was obviously confused, but also intrigued and then completely derailed from however he thought the call was going to go. And then within a few months were working together. So Jeff's whole career, when he looks back, is like a string of these types of moments. Finding what the person on the other end needs before they ask for anything and then showing up as the answer before anyone had to ask the question. He built solutions to the problems that they didn't even know that they had and then offered them before they knew they were even aware of the problem. And then now they are on the phone, realize they have a solution. And so he wanted to partner with Neil Patel on this, but instead of just going like, hey, I have a pitch, let's do this, he just just went and sold a six figure digital marketing contract and then was like, hey, what should we do about this? Where do I send the money? Also, how do we do this? You know? And that's what ultimately ended up building a digital marketing agency with, with Neil Patel, who's again one of the smartest marketers I've ever met. So then they sold that. Neil went on to build Neil Patel digital, which is a massive nine figure marketing agency marketing firm. And then Jeff went on to build Everbowl after that. So relationship capital compounds people. I don't know how many times I have to say it. Obviously the show before was called build your network. I have Travis makes friends, I talk a lot relationships. Relationship capital compounds. Just remember, people usually bring opportunity. Your competence is what allows you to capitalize on that opportunity. But people matter. Relationship capital matters. And it definitely compounds over the years when you build a reputation that says that you treat people the way that they should be treated. So lots of great stuff from my buddy Jeff. I highly recommend go check out the full episode I did with him on our show. As well as his own show, he's got his own podcast, the Jeff Fenster show, where he's had people like Gary Vee and Daymond John and all the best of the best on that show as well. And, and I'm a little biased because we actually helped him build out that show. So, you know, shameless plug. If you are an entrepreneur and you want a podcast that's built out for you, you know, hit me up travel.com. maybe we can work together like we did with Jeff. Anyway, that's it for this episode of the show. Thanks so much for tuning in. We'll catch you guys next time. Peace.
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Episode: SOLO | Make Money by Solving Problems Before Everyone Else with Lessons from Jeff Fenster
Host: Travis Chappell
Date: July 1, 2026
In this solo episode, host Travis Chappell distills key lessons from his extensive time with serial entrepreneur Jeff Fenster. Drawing from Jeff’s unique and varied entrepreneurial journey, Travis shares actionable strategies on unconventional problem-solving, decision-making frameworks, fundraising truths, capitalizing on personal pain points, and the compounding power of relationship building. The episode is packed with practical advice and real stories, tailored to listeners eager to make more money and live fuller lives—without giving up today’s joys for tomorrow’s promises.
[00:43 – 03:20]
Travis [02:10]: “Before you just use the solution that everybody's using, look for a different angle... Sometimes that ignorance can be really helpful.”
Actionable Takeaway:
If a standard solution isn’t working (or is just average), pause and reframe the problem. “Look for a different angle, be unique, be different, stand out.”
[03:21 – 06:50]
Travis [05:55]: “For the most part, the worst case scenario is really not that bad... You’ll just find if you do this exercise, I think that the worst case scenario is typically not as bad as you're thinking it's going to be.”
[09:34 – 11:10]
Travis [10:15]: “Money is not everything and it will not solve all of your problems. And sometimes it actually injects more problems into the situation.”
[11:11 – 13:18]
Travis [12:10]: “Solving that problem really well created an entirely separate, massively scalable company... Solve your own problem and you might accidentally build a business.”
[13:19 – 15:52]
Travis [14:37]: “People usually bring opportunity. Your competence is what allows you to capitalize on that opportunity. But people matter. Relationship capital matters. And it definitely compounds over the years...”
On Problem-Solving:
“If you find yourself coming up against the problem before you just…use the solution that everybody's using, look for a different angle.”
— Travis [02:10]
On Risk Assessment:
“Which would you rather have? Which worst case scenario would you rather have?”
— Travis [04:12] (Explaining Jeff’s crossroad decision-making)
On Taking Money:
“Never, ever, ever, never assume goodwill from people whose job it is to maximize return on capital.”
— Travis [09:50]
On Entrepreneurial Opportunities:
“Solving that problem really well created an entirely separate, massively scalable company...”
— Travis [12:11]
On Relationships:
“Relationship capital compounds, and it gets you meetings that you know don't make sense.”
— Travis [13:20]
Travis’s tone throughout is friendly, direct, and practical—a mix of frank storytelling and motivational challenge (“don’t just do what everyone else does”). He’s unashamedly pro-risk (where calculated), pro-networking, and very much about empowering individual, actionable moves toward making more money—not just budgeting or penny-pinching. The episode concludes with a plug for Jeff Fenster's podcast and an open invitation for listeners to build out their own podcasting platform.
To Listen Further:
Check out the full Jeff Fenster interview on the Travis Makes Money podcast, and give Jeff's own show (“The Jeff Fenster Show”) a listen for even deeper dives with top business leaders.