Why You Must Love the Problem You Solve - Caleb Avery - S6 - E11

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👤 Connect with Today’s Guest – Caleb Avery

Website: https://tilled.com
LinkedIn: https://www.linkedin.com/in/caleb-avery/

What does it really take to build a fintech company from scratch?

In this episode, Caleb Avery, Founder and CEO of Tilled, shares his journey from going door-to-door selling payment solutions at 19 to building a company redefining embedded payments with “PayFac as a Service.”

Caleb opens up about the early days of entrepreneurship, the reality of startup life, and a defining moment during COVID when he had to decide whether to go all-in on his business while supporting a growing family.

We also discuss why balance may be a myth, how to be intentional with time, and why founders must choose problems they’re willing to commit to for the long term.

What you’ll learn:

- Why most founders misunderstand “balance”
- How Caleb built a fintech company from real market needs
- The importance of being intentional with your time
- Why passion for the problem matters more than the idea
- How to think long-term as an entrepreneur

LinkedIn

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leogestetner.com/leo

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Transcript

Leo Gestetner (00:00)
Welcome to a Founder's Life. I'm your host Leo Kastetna. On the show, we dive into the real stories behind the highs and lows of entrepreneurship and how we pursue a more balanced and meaningful life along the way. This podcast is sponsored by Thanks, helping founders like us scale with reliable remote talent. Now, I'm excited today to be joined by Caleb Avery. Caleb, thanks for joining us. Can you kick things off by introducing yourself, please?

Caleb Avery (00:24)
Yeah, absolutely. So on the personal side, father of three living in Colorado on the business side, I've been in payments my entire career. That's really where I grew up, started my first company at 19 years old, going door to door, selling payments to small business owners, and then have really grown up in the payment space throughout my whole career. So between the first company and the company I'm running now tilled, I did a lot of consulting and angel investing for vertical software platforms, most

helping them leave Stripe so that they could figure out how to better monetize the payments going through their platform. And after a couple dozen of those engagements, really seeing the same problem over and over again where the companies were frustrated by either the technology, the support or the experience that they were getting from the alternatives to Stripe, I decided to go start what became Tilled and what we call PayFac as a service.

Leo Gestetner (01:14)
Excellent. tell us a little bit about, you sort of gave a little touch there, but tell us about your journey that brought you where you are today. And then also more about what Tilde is doing differently for your customers and how you're helping them.

Caleb Avery (01:27)
Yeah, absolutely. So, you know, the experience on the consulting side, if you think back 10, 12 years ago, these software companies really had no idea that they could actually generate revenue on the payments that were flowing through their platform. And so depending on your perspective, I was either the good guy or the bad guy coming in to let them know that they were leaving in some cases, millions of dollars in revenue on the table. And so the journey for me was really getting in deep with these software companies, helping them understand what the options were that were available.

things like NMI or authorized dotnet and then helping them negotiate relationships with a lot of the legacy processors. And after I kept seeing these same challenges over and over again, it felt like maybe I would be the right person to actually build a proper stripe alternative. And so for me, I set out in January of 2019 to build what became tilled. And the early days, it was really just me. So I was trying to figure out, OK, can we actually solve the technical challenges?

We solve the legal challenges. Will the banks actually allow us to go to market with this PayFac as a service model? And so we were really the first company to create this concept of PayFac as a service. And so we were the ones paving the way, which now a lot of our competitors, you know, have since come in and tried to replicate the model. But it's been a pretty incredible experience over the last seven years, just getting to work with some incredible partners and build out this business.

Leo Gestetner (02:50)
Excellent, you brought your experience of what needed to be done and like many entrepreneurs it came from your need, your understanding of what was needed. Talk to a little bit about what family looks like for you.

Caleb Avery (03:02)
So I've got three little kiddos at home so daughter about to be eight and then two rowdy little boys one six and the other is about to be three and so life at home is pure chaos with with three little kids I honestly can't can't imagine life without them but it sure sure is a lot of work

Leo Gestetner (03:19)
Yeah, but nothing quite like kids. mean, mine are now 20 and 23 and yeah, loved all of it with them and I continue to. I think that there's nothing quite like that relationship.

Caleb Avery (03:22)
It's the best.

Yeah.

I feel like this age that they're at especially is a pretty fun age. So at this point, like they actually want to spend time with me. And so I travel a ton for work. But when I am home or when I'm about to leave, they're either incredibly happy to see me or very sad that I'm leaving. And I know a lot of like my colleagues that have older kids or teenage children, you kind of lose that that connection with them. Or all of a sudden they're like, oh, I didn't realize you were out of town for, you know, two or three days. And right now I'm in that sweet spot where they just want to hang out.

they want to play, they want to have fun and it's a pretty magical time.

Leo Gestetner (04:05)
Yeah, I think whether you lose it later really depends on the relationship you have with the kids. So you lose a blind devotion. You lose, you know, the puppy dog glad you're coming home. But if you're present and purposeful, you know, I mean, the kids continue want to spend time with you and they still miss you when you're gone and you can have real quality time at any age. And I can say that firsthand.

Caleb Avery (04:11)
I love that.

Well, I guess that's what I aspire to. So maybe we're planting the seeds right now and we'll get to experience that over the next 10, 20 years.

Leo Gestetner (04:36)
Definitely. And what does health look like for you?

Caleb Avery (04:39)
Yeah, I would say for me, I spend a lot of time golfing, skiing, biking, and so trying to be outdoors as much as I can. I'm not what I would consider a gym rat. That's not my lifestyle, but try and sleep well, try and eat clean, and then get outside and do at least my version of exercise, which my preference would be golfer or skiing.

Leo Gestetner (05:03)
We're living in the right place for it.

Caleb Avery (05:04)
Colorado definitely makes it easy and I feel like especially this winter the weather was just absolutely incredible and the other reality is having three little kids we're always at a playground or we're outside kicking the ball or we're going to a ninja gym or a trampoline park and so I get no shortage of exercise just trying to keep up with the three of them.

Leo Gestetner (05:26)
Have you got the older ones skiing yet?

Caleb Avery (05:28)
you

So I have the two older ones skiing my eight year old certainly much better than the six year old, but we started them young. So I think my daughter started at three. My now six year old started at two and a half. And so we take them up on the little bunny slopes, ride the magic carpet up. And I still remember my then two and a half year old son. He saw that there was a little jump on the bunny slope and he wanted to go over the jump every single time that we were taking him.

down the mountain. And so we're finally getting to the point where they can start skiing on their own. And I feel like that's the payoff from years of either me trying to teach them or paying for ski lessons. Finally, they're they're kind of at that point where like my daughter can go up, she can ride some green trails and ski on her own all the way down. She's doing turns. And then the six year old occasionally still wants to hold my poles or if it gets a little steep, I got to carry them down. But they just love being out there.

Leo Gestetner (06:23)
and then give it a few years and they'll be skiing better than you are.

Caleb Avery (06:26)
That's honestly, that's the goal. I hope we get to that point. I feel like for me as a parent, like that's how I know I've won. If they're better than me, whether it's golf, skiing, basketball, I'll be thrilled the first time that they beat me at anything.

Leo Gestetner (06:39)
I definitely my kids are both substantially better skiers than I am now and I've been skiing all my life. But, know, or weightlifting, you know, I got my son into weightlifting five years ago now and I always said to him, you know, the aim is you should be lifting much heavier than I am. And, you know, he is now lifting substantially heavier than I am and, you know, you can see it. He's loving it and he's, you know, got the...

the muscular to show it.

Caleb Avery (07:05)
There's also a huge benefit to starting them young. feel like their fear factor when they're starting at two or three is almost zero. So for me, I grew up snowboarding. And so on a snowboard, I was fearless. I'd go in the terrain parks. I'd be doing jumps and rails and anything. But I switched to skiing in my 20s. And in your 20s, you realize you are breakable. You can get hurt. And you're not invincible. And so my level of fear on skis versus a snowboard is massively different.

and even though at this point I'm probably a better skier than I ever was as a snowboarder, but I started so much later in life that like my brain is like, nope, you should not go off of that jump. You should not try and do these rails. You're not five anymore. Don't do that.

Leo Gestetner (07:47)
And I don't know if it's that the little ones don't break anything, as in just their whole body's a little more flexible, or if they're so close to the ground that they can fall over, roll, and carry on going. Yeah, and what do you like to do for fun? Obviously, a lot of what we've just been talking about, but what do you like to do for fun?

Caleb Avery (07:54)
Definitely a factor. Yeah, the low center of gravity is nice.

Yeah, I would say for me, given how busy I am with work, I'm basically at the office traveling for work or I'm trying to spend time with the kids. so for me, like if I look at my hobbies and activities, skiing tends to be with the kids and golf tends to be for work. so last year, I think I got something like 25 rounds of golf and I think two of those were in Colorado. And so for me,

That's one of the, I guess, sacrifices that you make is if you want to be actively involved in the business and you want to be actively involved at home, like something has to give. I think for me, that give is the free time for me with my hobbies. And so I try and basically allow my hobbies to either be involved with work. Let's go take clients out golfing and do business on the golf course. So I'm happy, but I'm also, you know, working.

you know, let's go do activities with the kids and then I'm getting out, I'm having fun, but also getting the quality time with the kids.

Leo Gestetner (09:09)
Nice and I guess the question is when will the kids be good at golf as well?

Caleb Avery (09:13)
we'll see the two and a half year old is the most interested in golf so he is pretty much the the little mini me and so he'll have our nanny take him to go pot pot

at least twice a week and so I've got an unbelievable amount of videos on my phone of him getting holes in one at putt putt which to me I'm absolutely thrilled that he's just excited to go out and do it and I've got a little golf simulator set up in my garage and I've got videos of the little guy he could barely stand and he'd be out there just wanting to hit balls and now I've come home a couple days over the last few weeks and

My six year old has been out there by himself in the garage starting to hit balls and so to me I try not to like push that hobby or know that interest onto them and make it something that they're excited and want to get into. The byproduct of that is they're starting a little later than I would like but hopefully they'll be more excited to pick it up because it's their own interest and not dad saying we gotta go to golf camp. You gotta get out here and do this.

Leo Gestetner (10:15)
And there's no hurry they'll catch up. And how do you look at a balanced life? So for you, you've got obviously, you all the different aspects. How do you ensure that there is overall some balance? Now, I always talk about that as, you know, sometimes we're more in balance than others. None of us are permanently in balance. Sometimes there's a big deal or there's lots of work you've got to do. But how overall do you look at a balanced life?

Caleb Avery (10:36)
Yeah, I don't particularly believe in the concept of balance. I think to me, the reality of being a startup founder, CEO is that I'm inevitably spending a tremendous amount of time at the office traveling for work. Like that's where the bulk of my time is going. And so to me, I think about it more in terms of being intentional and setting boundaries with my time. And so for me, a lot of that comes down to when I am home, when I am with the kid,

It's trying to be intentional about being present and spending that time with them and not being on my phone and then a lot of it for me also comes down to I want to be that actively involved parent when I am with them and so this past weekend we went to a kids birthday party most of the parents are hanging out, know chatting amongst themselves I'm out in the bouncy castles hanging out with the kids playing and like for me That's that's my time to go spend you know with them and so it's being intentional

about, hey, this is the time that I'm dedicating to family, I'm going to go make the most of it. And then when I am working, being intentional about, OK, I'm in the office, let's get as much done as I can in the hours that I have available here. I think by being intentional in kind of which mode that I'm in and then setting those boundaries and saying, OK, hey, for the next four hours, I'm going to go be with the kids. I'm going to leave my phone in the diaper bag and be present. And I think that's what allows me to be the best

version of myself that I can whichever mode that I'm in but I still don't still feel that there's the the balance I'm not sure that that's an achievable standard

Leo Gestetner (12:06)
See, I'd argue that is the balance. The balance is that you're at some point, yes, you're working hard, but at other points you're playing hard with the kids. That to me is balance. It doesn't need to be a permanent balance. It's finding time for those different aspects in your life. And what has been a pivotal moment in your life?

Caleb Avery (12:22)
I think for me, COVID was a really interesting time, both personally and professionally. So on the personal side, my now six-year-old was about three weeks old at the start of COVID. And so that was a really, really difficult time for us where we thought we were going to have a lot of childcare to help with the second kid, because we still had another young one at home. And then I was meant to be really focusing on the business

And the childcare pretty much evaporated right at the start of COVID, because everybody was pretty worried about their own families, their own health. so I spending a lot of time at home caring for a newborn. And at the same time, I was in the middle of starting a business. And so it was a really critical time for Tilled. And if you think back to what was going on at the start of COVID, small businesses were closed. And for me,

a lot of the.

the cash to build up the early days of till came from my first business where you know still get some mailbox money today but it's all based on small business owners processing credit card transactions so start of covid all these small business owners were closed and so I'm sitting at home I've got a newborn another small baby income starting to dry up I'm trying to go build a new business and I remember having this conversation with my wife where she's like do you really believe in until does this really

something that you want to go build. At that point I had to make that decision of like, how all in am I on this business? whatever, six years later pretty glad that I stuck with it and pretty glad that she believed in me to let me keep going.

Leo Gestetner (14:00)
And that moves nicely on to the next question which is what is one piece of advice you'd give to an aspiring entrepreneur?

Caleb Avery (14:06)
Hmm. I think for me, I get a lot of inbound from entrepreneurs that are thinking about starting businesses. And one of the questions that I always ask them is like, is this a business that you'd be excited to run 10 years from now? And

Sometimes the answer is, you know, absolutely. I love the problem. I love the team. love, you know, the journey that I'm on. And sometimes you get this weird look from them where they're like, I don't want to be running this business 10 years from now. And I think for me, just having been in this business for seven years and having run, you know, my prior company before that, the reality is you have to be incredibly passionate about the problem you're solving, the market you're entering, the team, you know, you're going into battle with.

you've got to be prepared to endure that marathon of running the business because it's not a sprint. There's not a lot of businesses that, I'm going to run this for 12 or 18 months and have this incredible exit. Usually the gains and the wins come from that compounding of years and years and years grinding it out and spending the time to get there. And so that's the question that I like to ask. And I guess the advice is be prepared

to find that pace that you can sustain and make sure that you're running a business in a space that you're really passionate and excited about.

Leo Gestetner (15:25)
That's great advice. And how can people find you?

Caleb Avery (15:29)
so i'm very active on linkedin that's pretty much the only social media but i have to not gonna not gonna find me on facebook

Twitter, Instagram, none of that. But LinkedIn's a great place to find me personally and come follow Caleb Avery. You'll get a lot of business, a lot of golf, a lot of kids. If you like that combo, come follow me. If you don't, probably not a good place to follow along. And then our website, Tilde.com, is a great place if you want to learn more about Tilde, PayFact as a Service, embedded payments, monetizing payments, all those buzzwords.

Leo Gestetner (15:56)
and thank you for joining us today.

Caleb Avery (15:57)
yeah thanks so much for having me on the show really enjoyed it

Leo Gestetner (16:00)
Thank you for listening to today's episode. you enjoyed the conversation, don't forget to subscribe to channel, tell your friends and please leave a review.