In short
David Phillips (Fondo) discusses solo founding after multiple co-founder breakups, including how he pivoted a nearly failed company (Bloomjoy) into Fondo, how to handle emotional/legal cap-table issues, and how to get early customers by building trust through “mini products” and free value.
Guest background
David Phillips is a solo founder and former accountant (Deloitte). He previously co-founded multiple startups, including a tutoring marketplace in college, a Deloitte-hackathon startup that he was fired from after raising a seed round, and a coding-bootcamp venture that was later acquired. He also invested in startups before founding Fondo.
Key claims
Solo founding is “hard mode” but builds resiliency and resourcefulness; trust is built by adding value; free help can convert into customers; enduring startup needs (like accounting) beat short-lived opportunities; when co-founders leave, prioritize cap-table functionality and move quickly with good legal counsel.
Notable examples
Restarting with $40k left after failed acqui-hire negotiations; getting first Fondo customers by offering free Delaware franchise tax filings, then pitching bookkeeping; early traction for a coding bootcamp via free teaching; initial Fondo sales wedge via The Hustle founder Sam Parr.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOThe Challenges of Co-Founding
0:45 to 4:40
David discusses his experiences with co-founders and the challenges faced.
“You're one of the first people that I met that was actually a solo founder.”
Transitioning to Solo Founding
4:40 to 7:50
David shares his decision to go solo after multiple co-founder experiences.
“Fondo has sort of achieved a lot more milestones that I had previously with my other companies.”
Refounding and Investor Relations
7:50 to 10:00
David explains the process of refounding his company and handling investors.
“And they started, you know, absorbing our customers.”
Navigating Co-Founder Breakups
10:00 to 16:43
Discussion on the emotional and logical aspects of co-founder breakups.
“So, but we just did it, you know, I just sent the email and was like, I'm going to try this idea called Fondo and I'll update you in six months if it's going well, or if I'll try something else.”
The Importance of Investor Relationships
16:44 to 18:14
Discover strategies for effective communication with investors during tough times.
“And when navigating sort of, um, a transition like this as a founder, I know that you said that you were, you know, pretty nervous about talking to your investors.”
Building Fondo: A Reflection of Experience
18:53 to 24:24
Explore how past experiences shaped the creation and success of Fondo.
“And also I think that there's something to be said about solo founders.”
Finding the Right Business Idea
24:25 to 28:00
Understand the process of filtering ideas to find the best entrepreneurial opportunity.
“I think, you know, during that moment where I was like, okay, we're going to pivot the company to something new.”
Transitioning from Past Ventures to Fondo
28:00 to 29:23
Learn how David Phillips analyzes business sustainability and market needs.
“domain that I was recently learning about.”
Finding Unique Insights for Success
29:23 to 30:58
Discover the importance of leveraging personal experiences in startup ventures.
“It's like you combine those two things and that feels like what makes Fondo special.”
The Dynamics of Working with Family
30:58 to 32:57
Explore the advantages and challenges of collaborating with family in business.
“you know, all everything, you know, when you're building a startup, you are starting from nothing, right?”
Show all 17 chapters
Acquiring the First Customers for Fondo
32:57 to 36:29
Understand the strategies David used to get the first users on board.
“There's, of course, all sorts of other, you know, things that can go wrong, right?”
Building Trust Through Value-Added Services
36:29 to 38:41
Learn how offering free services can establish trust and lead to business growth.
“I was like, oh, this is actually a really interesting wedge.”
Supporting the Startup Ecosystem
38:41 to 41:32
Discover how Fondo aims to uplift other founders and the startup community.
“I mean, I think the other thing that kind of comes to mind is sort of this like mini products or like things that are free value, um, that you can give to people that really are helpful and meaningful.”
Creating Opportunities for Founders
42:01 to 43:15
Discover how podcasting can open doors for founders and foster success.
“Um, but maybe, yeah, what, what are some of the reflections, uh, after having sort of worked on this stuff to like lift up people in the ecosystem and promote other people?”
The Bear Case for Solo Founding
43:15 to 46:56
Explore the challenges and difficulties of being a solo founder.
“The first question is the bear case for being a solo founder.”
The Case for Solo Founding
46:56 to 49:15
Learn about the benefits and unique strengths of being a solo founder.
“I think, um, you know, we haven't really talked a ton about, you know, what starting a company today looks like, right?”
The Evolving Landscape of Solo Founding
49:15 to 51:47
Understand how technology is reshaping the solo founding journey.
“Like, you know, uh, Claude Code and like Cursor and like, um, like you can, you can build things really fast.”
Transcript
Automatic transcript. May contain errors.0:00David J. Phillips:We had$40 ,000 left in the bank. I'll just like restart the company with a new idea. Had these four previous co-founding experiences that didn't quite work out. So I was like, okay, let me try this solo. Did a post on Bookface. Who needs help with Delaware Franchise Tax? We got like 100 companies to sign up for that. Pitched those 100 people on bookkeeping. And that's how we got like our first 10 customers. You need to build trust. The best way to build trust is adding value. The bear case is it's just really hard. It's really hard to start a company and make it successful, and it's even harder alone.
0:30David J. Phillips:What is the case for solo founding? When you're a solo founder, you're just forced to be even more resourceful. Default co-founders happen when you don't want to do the hard thing. Everyone has a co-founder in their pocket now. There's no excuse. You can build anything. So go solo. You're one of the first people that I met that was actually a solo founder. Yeah, it all started with a Zoom interview with you back in 2020, right in the beginning of the pandemic. But yeah, I mean, I think my journey with founding in general, like goes way back to, you know, when I was in college, and I had my first startup, we built a tutoring marketplace, and I had a co founder.
1:09David J. Phillips:And it was amazing had all these like, first learnings of building a company and, you know, how to get how to get customers how to how to build a team, and like working with the co founder. And then, you know, after college ended, you know, I moved up here to San Francisco. He stayed in Southern California. And we just kind of had this like, you know, disconnect about like how are we going to build, you know, this thing that we started. And ultimately, we're just like, we can't, you know, we have to split. And so that was like my first co-founder like split thing. And we ended up just kind of like building two separate companies doing the same thing.
1:49David J. Phillips:and you know it it's kind of a a common thing like co-founder breakups that was my first one and then since then you know I did my my first sort of San Francisco startup after I moved up here I was working at Deloitte but I really wanted to get into startups and you know do my own thing and was going to hackathons won this hackathon partnered up with somebody there and you know heard the advice, like, don't, don't co-found a company with someone you meet at a hackathon, but we did it anyway. And, and, you know, we raised a seed round and then he fired me, you know, six months later. And so there I was again, sort of like in another co-founder breakup and, you know, fast forward, you know, to my next company, decided I wanted to learn to code like that first, you know, that, I guess, second company where my co-founder fired me, you know, I was the non-technical founder.
2:43David J. Phillips:I probably wasn't contributing as much to product as I could have if I was more technical. And so I really had this, after that experience that I wanted to become more technical, I wanted to be able to contribute more. And so I learned how to code and then started a coding bootcamp and did that with, you know, iterated through several ideas before that coding bootcamp started with other co-founders that we ended up splitting as well. And like each time I was starting these companies with co-founders, we would always ultimately end up sort of going our separate ways. And sometimes it was like really amicable.
3:15David J. Phillips:Sometimes it was like really not amicable. And, you know, that coding bootcamp we started, we grew it, you know, my co-founder of that left a couple of years in and ultimately we got acquired and it was a great outcome for everybody. And, you know, when it came to, after that, I started like investing in startups and wanted to start another company myself and did it again with, uh, as a solo founder, you know, um, decided, okay, I've had these, you know, four previous co-founding experiences that didn't quite, uh, you know, work out. And, uh, from like, you know, a team perspective. So I was like, okay, let me try this solo.
3:53David J. Phillips:And I started solo and then quickly, um, got a lot of anxiety building solo. I was like, ah, I don't know if I can do this without a co-founder. You know, I got into YC and I was like feeling the pressure of trying to build something really quickly and go to market really quickly and grow really quickly. And I decided to bring on two co-founders and, you know, we built that version of this company for almost two years and then that company didn't work out. And, you know, my co-founders left and kind of had this refounding moment of the company and started Fondo as a solo founder now. So I kind of just, from my experience, I tried it with co-founders so many times.
4:36David J. Phillips:And ultimately, with Fondo, which has been, you know, my most, you know, the most fun I've had starting a company, Fondo has sort of achieved a lot more milestones that I had previously with my other companies. And so solo founding just worked out for starting Fondo. But it really, for me, it came from all these experiences with co-founders that I was like, okay, I think I need to really do this as a solo founder now. For that transition to solo, because you actually had some, you started solo for Fondo, or what eventually became Fondo. I forget if it was actually called Fondo. It's called Bloomjoy.
5:14Yeah, so you had a bunch of different names. You had a bunch of different products. you started solo but then you got co-founders because this sort of anxiety around potentially being solo being solo um you know it was still uncommon but it was especially uncommon back then um i'm curious uh sort of how you think about sort of that that journey of founding right because there's ultimately sometimes many founding moments of a company or even if it's the same entity it's like a completely different company so you know you you started solo and you had these co-founders but like effectively it was a brand new company just with the same shareholders when you actually started Fondo.
5:52Can you share a little bit of what that's like and sort of how you have to communicate that to investors or if you had anybody on your team other than your co-founders at the time? Because I think that it's such a common circumstance that's really under discussed, which is I have co-founders. It's not working out. Do I shut the company down? Do I keep going? I want to keep going, but what's the right thing to do? How do I actually handle that? How did you handle that at the time?
6:19David J. Phillips:Yeah, it's a, it's an interesting position to be in. Um, and there's so much different, uh, feelings around it, right? You know, on the one hand you have, um, you know, whatever happened with your co-founders and whatever's going on there, you have investors that you committed to, um, you have customers that you committed to, maybe you have team members that are already a part of the journey. And, you know, you have to sort of restart the company. And there's a couple things you can do. You could restart the company, you could shut down the company. And we kind of faced this decision. We actually were in the process of trying to sell the company.
6:59David J. Phillips:And we went through months of negotiation, we had, you know, we ran a process, we had a couple of interested people in buying the company, ultimately decided on one company, and we were running out of money. So the company was Bloomjoy. We had a team of about 15 people and, you know, we were running out of money. So we decided to run a process to try to sell the company. We had, you know, conversations with a bunch of people, decided on this one company. They were a great fit. And because we were running out of money and we couldn't make payroll during the negotiations, we're like, why don't you just hire our team?
7:33David J. Phillips:And so that they can like, you know, keep getting paid. We'll transition our customers to you. And then we'll like, we'll finalize the, you know, the stock purchase agreement later, or as we're doing all this stuff, because, you know, we trust each other and everything. And, you know, they hired our team, which is great. And they started, you know, absorbing our customers. And then like, we just couldn't come to terms on that stock purchase agreement. There was, you know, this concept of an earn out. You know, it wasn't like a huge acquisition. It was basically a acqui-hire. And, you know, we would make, you know, the company had raised about a million dollars.
8:14David J. Phillips:We would, you know, our investors would get their money back over time. Ultimately, the deal would have been worth something. But defining how that like gets unlocked, you know, once the deal is closed, like we couldn't get clear definitions around it. And so it was like, this was taking forever, it was dragging out and it was, you know, had a conversation with my co-founder was like, let's just like, like at one point it was just so exhausting to like, keep trying to negotiate this. It was like, let's just end this. Like it's over. We're not going to sue them for like stealing our customers and hiring our team and not doing the deal.
8:51David J. Phillips:Like it's over. And, um, you know, we had like$40 ,000 left in the bank and, um, we'll just, um, I'll just like restart the company with a new idea. And the reason I wanted to restart was because, you know, we did raise a million dollars, you know, it's not a huge amount of money, but it was from friends, it was from investors that we want to build a good relationship with. And I just didn't want to take that loss, you know, that loss of shutting down the company, no one getting any, no, get no one getting a return on their investment. And, you know, the decision to like move forward with these existing investors and this cap table just made more sense than like flushing that and starting over again.
9:33David J. Phillips:And so that was the path that we decided to take. And because it was an amicable parting of ways with my co-founders, like the cap table was good. We were in a good position where it made sense to keep moving forward with this entity. But it was a tough decision. I remember writing the investor update. How do you tell investors that the deal you've been telling them in the past, like three investor updates is like not happening anymore. And you're going to pivot the company and, you know, co-founders are leaving. So, but we just did it, you know, I just sent the email and was like, I'm going to try this idea called Fondo and I'll update you in six months if it's going well, or if I'll try something else.
10:12I mean, it's, it's a really good story because it brings up all sorts of topics that we can talk about. I think the first one is, is like from a practical perspective, if you're a founder who's in a similar position to what you were going through, like what would be the advice that you'd give for them about how to handle that? I mean, I assume that there's a couple of pieces that are really important. One of them is if the co-founders have been around for a long time, like they've probably vested a significant amount of the company. And if you're going and starting a brand new business that has completely different customers, you know, completely different product, this is something where you obviously want to support the co-founders, especially if it was amicable and they weren't making it difficult, you know, to build the company.
10:57But at the same time, you want to make sure that you have like a cap table that can function as a new company. You know, investors maybe have different opinions about what you should do. Some, the best investors are often very supportive of continuing on, you know, keep going, that sort of thing even if it maybe is sort of like a thing that some a lot of founders might have decided to wind down the company or start fresh I'm really curious like um if you were to sort of give some practical advice around uh co-founders around that sort of thing for people who might be going through a similar thing because I think the reality is like more often than not that actually happens this isn't like some like edge case hypothetical I think this is very real and very often people don't have this uh don't have any sort of knowledge about what other people have done or how they might best approach it.
11:45David J. Phillips:Yeah. I mean, it's, it's super, yeah, there's no blog, there's not many blog posts about this. And I first encountered this with my first like SF startup where my co-founder fired me. And I was like, you know, that was like such a blow. You know, my first company, we had like VC backing, everything was exciting. And then like, you know, you're the, I was the co-founder, you know, getting let go. And, you know, I talked to a bunch of lawyers. At the time, I was pretty new to SF. I didn't really know startup lawyers, but my dad had a good friend from high school who was a real estate attorney. So I spent some time with him.
12:21David J. Phillips:You know, I ended up, you know, also through my dad, he had, you know, worked at Microsoft with a guy who started a startup and was venture backed and he connected me with him and he connected me with his startup lawyer. And so, you know, found a connection to a good lawyer. And he basically told me the best thing I could do is just like move on as quickly as possible. And I shouldn't try to sue the company. I shouldn't try to cause problems because like, you know, what's the point of that? And how do you vest it at this point for that company? I was like, you know, less than a year vested, but I had no, I had no cliff.
12:56David J. Phillips:We didn't do any cliffs. So, you know, I didn't have I had some, you know, I had a meaningful share, but nothing, you know, it wasn't too complicated for my co-founder there to just like, okay, you vested this, like, let's move on, you know, but I could have, you know, first time founder, I thought I deserve so much more, right? I founded the company, blah, blah, blah, right? But this advice from the lawyer was like, just move on as quickly as possible. Like, don't, you know, you own part of this company, suing the company or causing any distraction for them is ultimately going to hurt you. And so you own some of it.
13:32David J. Phillips:So just wish them best. Like you really just want them to succeed so that you can ultimately, you know, get some value for your equity and move on to your own thing. And so, you know, I just took that advice and like, I, you know, got a severance and got my stock and, and just moved on. And, and so when I, you know, that was a big lesson for me. and you know fast forward to now this case was just like yeah how do we how do we just move on from this you know what does everyone want to do after here I'm going to completely pivot the company to something completely new and so yeah just have a very like logical discussion about it and and everyone you know because it was amicable everyone was on the same page and it the cap table was good from there but I do think you know it is complicated when you have you know two years of vesting.
14:21David J. Phillips:And, you know, you have to, you know, if you're going to move forward, you want the cap table in a position for success. And you have to negotiate that, you know, with your co founder, and it's not easy, but definitely finding common ground and being logical helps. How do you think about, and we'll talk about the investor stuff in a second, but how do you think about kind of i think that oftentimes there's two aspects of this is the logic and there's the emotion yeah and uh and if you try and bring logic to an emotional situation it usually doesn't work well you try and bring emotion to a logical situation you know it also it's sort of like uh you know water and oil or something yeah they don't mix so like how do you actually and this is maybe more of a meta question not specifically tied to this but i think this is like a certain example of where this is often going to happen.
15:20How do you sort of do that? How do you sort of like deal with emotional situations and sort of like meet people where they are versus, and, and, you know, the same thing with like logic. Like I think logic is, is always the thing that people wish is the default. Right. But, but emotion is, is often the thing that ends up coming out, especially something where somebody is dedicated a lot of time. It could be a co-founder, it could be a, you know, teammates, that sort of thing. Totally.
15:43David J. Phillips:I mean, I think, you know, hoping and encouraging that you're like the other side has really good startup legal counsel, right? Because a lot of times in these founder breakups, you might end up with a former co-founder who has a real estate attorney helping them out on the side, right? And they're like, well, you own 50%. Like, what is this vesting thing, right? Like not everyone, not every attorney understands vesting and cliffs and things like that, right? So you really want them to have an experienced startup attorney on that side to guide them with that advice of like, just move on. Like you're going going to, you're going to nuke the company, like take, you know, take some position in the company and wish them the best, you know?
16:19David J. Phillips:So yeah, helping make it clear that they should have good counsel, like kind of, um, it's not necessarily you telling them that they need to do this for the betterment of the company, but they have like an independent third party that's actually on their side telling them what's best for them and for the, um, yeah, what's best for them. Because if they're a shareholder in the company, ultimately what's best for the company is best for them. Right. So you just want to, yeah, help, help, help them get that, that advice. And when navigating sort of, um, a transition like this as a founder, I know that you said that you were, you know, pretty nervous about talking to your investors.
16:55Um, how do you like, how do you sort of think about just like communicating with investors generally?
17:03David J. Phillips:Yeah, I think it's good to always have, um, some investors that you're close with, you know? So, um, I, I'm really close with, uh, Chris and Peter who are partners at, uh, Transmedia Capital. So they sort of backed me in my previous company. You know, Chris was actually someone who was giving me advice when I got fired from my first company, um, cause he was hosting the hackathon that, uh, that we won. So, uh, he's always been in my corner. And so, um, you know, when this was happening now with this, this new company and, um, the pivot and, you know, I went to lunch with him and his partner, Peter, and I was just like, you know, I'm thinking about this thing, you know, and, um, you know, I'm not sure if I should do it or if I should tell the investors or whatever, and just got, you know, them supporting me like at that lunch, uh, just having their support, you know, they weren't even our largest investor or, um, you know, but just knowing that they were in my corner for this just helped me have that confidence.
18:03David J. Phillips:It's like, okay, this is the thing I'm going to do. That really helped push me over. So finding a really close ally in your investor pool helps a lot. That's really cool. If you're enjoying this conversation, then perhaps you're starting your own company. And if so, you should apply for the Solo Founders Program. I've spent the last seven years working with startups and founders who are figuring things out. And I'll tell you, the ones that make the most progress are the ones who make sure that they have relationships that can help them go the distance. The Solo Founders program is about bringing 10 solo founders together so that they can build solo together versus building solo them.
18:40I'll work with you, we'll invest$100 ,000 and we'll make sure that you make the most progress that you possibly can in three months. If that sounds interesting, you should learn more and apply it at solofounders.com slash program. Maybe we can talk a little bit about sort of how Fondo is much, a very good like reflection of your past experiences and things like that. because I do think that as people go on and build companies, and especially if it's their second or third company, they tend to move towards things that maybe, or pivot even, they tend to move towards things that are maybe a better fit for them than maybe where they started.
19:17And also I think that there's something to be said about solo founders. When they do it really well, they end up finding something that's truly related to them versus it's just related to one of the co-founders. Usually most co-founder relationships, if there's two co-founders or three, there's one that's like really close to the problem, but the others are maybe a little bit more removed if not completely removed from it. And I've seen that work. We definitely see that work. You invest in startups. You've seen lots of startups over the years. you know that co-founders can have that where one is like deep subject matter background person and the other is more of like, you know, somebody who's just really good at whatever it is that they do and they can apply whatever it is that they do to that business.
20:02But I'm really curious how you think about how Fondo, the version of Fondo, like once you kind of were solo, you had 40k left in the bank, you know, out of a million dollars raised. Like this is a really big turnaround for the company and Fondo is doing really, really well now. It's like, it's considered like the company in its category. And I think that's really wonderful. Um, but maybe talk about how sort of your experience, um, led to like focusing on this and, and that's sort of like the very early days of Fondo. And then once you talk about that, I want us to talk about sort of how people can think about that themselves, like how they could actually put that, um, that frame of mind towards figuring out the things that maybe they could be working on.
20:44David J. Phillips:Yeah. I mean, it's a really good point. I think, you know, starting a company is difficult in so many ways. Right. And, um, putting together all the pieces of this like puzzle, right. To make this successful company, um, every piece can be really difficult. And, um, you know, when you have a co-founder, there's a process for like, for the way your company moves and like the speed at which it moves, right? And when you're solo, you're kind of unencumbered by that, right? That friction to take an idea from idea to market, you know, it really depends on the, you know, the dynamics between the co-founders, but, you know, sometimes it could work really well and you're both completely aligned and you go from idea to launch like super quickly and, or sometimes it's slowed down.
21:36David J. Phillips:Um, so having, uh, being solo, it's like pretty freeing in those early days of just like, I have this idea. I love it. I really want to do this and you could just do it right. There's no process. There's no friction. And, you know, I used to be an accountant. Uh, I started at Deloitte and I love accounting. I always would, uh, you know, all my companies, that was one way I'd get into like a flow state was like doing our accounting. And so, you know, I'd also during this previous iteration of the company, you know, we ran out of money and we weren't watching our runway as close as we should be.
22:11David J. Phillips:We were working with, you know, a different company to manage our books. It got too expensive. So we stopped. We were doing it in-house. You know, we had a friend of a friend doing it, you know, all these sort of like, you know, unideal ways of doing our books. And we just like lost sight of our runway. And, you know, that was a real problem that I faced with my company, even as an accountant. And so I just thought like, there's got to be, you know, all these startups that are managing their burn, their runway, like trying to build their companies. Like, if I as an accountant was having a hard time with that, I can imagine other founders that are not accountants at all facing it, you know, even worse.
22:52David J. Phillips:And so I was really excited about this idea for Fondo to just build the, like the accounting solution specifically for startups. So, you know, I had used other, you know, startups that do what Fondo does in the past. I have used accountants from, you know, Yelp, Craigslist, you know, we, we built accounting teams at my previous company. So I've sort of done accounting every way you can do accounting as a startup and was, yeah, really excited to build Fondo in a way that was just like specifically designed for founders running their company. So really easy to onboard, really easy to understand the information that you need to know.
23:29David J. Phillips:Really stay in compliance with all the random tax deadlines you have as a Delaware C Corp. So yeah, I was really excited about just making that easy. And so yeah, just just starting with that idea. Yeah, it was very freeing to just try it, you know, and try it without any friction, yeah why didn't you get there earlier you know what I mean like like it's it's really interesting because there's that whole notion of um do what feels like work for others but play for you right and uh and you just said like you know accounting is this thing that you actually really enjoy like doing this work with all you know these numbers and spreadsheets a lot of people would consider that dreadful right but but some people really enjoy it right and you didn't get to building Fondo until quite a while because what what how long was it since you actually started that company the company that became Fondo?
24:23David J. Phillips:It was two years. So yeah two years and you were working out a lot of other things and so it took you a little while and then you've worked at other companies before that right but after being an accountant at Deloitte right so how do you think it took so so long to actually get to the thing that's sort of like a core part of your interest than the things that you're talented at? I think, you know, during that moment where I was like, okay, we're going to pivot the company to something new. You know, I think a lot of founders keep that, you know, list of ideas that they have in their pocket, always, always, you know, jotting down ideas.
24:58David J. Phillips:And I think going through that list, you know, we had$40 ,000 in the bank. So, you know, going through that list of ideas, you know, running it through the filter of which of these ideas can I do solo? You know, which one can I get off the ground solo without needing more than this 40 grand that we have, where I'm really the domain expert and can empathize with the customer really well, can solve the problem really well, and, you know, take the existing, like, what are all the tools that I have, right, that I can use to, like, build something from scratch? And then of all these ideas, which one do I have the highest likelihood of making work without, you know, needing to raise money.
25:45David J. Phillips:And so, yeah, then Fondo just came to the top. So I think just being forced to like run all these ideas through that filter helped, you know, surface this idea that I really was well-suited to work on. Why do you think people don't get there, you know, in the early, like, like off the bat, right? Like, because what, because what were you working on? Like, maybe share a little bit about what you're working on with the co-founders and stuff. And is, is it feels like this is just such a good way to think about things generally, but like, this isn't where you started. No. I mean, so, you know, the previous idea I did relate to as well, but it wasn't as, I didn't have as deep of domain expertise.
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26:28David J. Phillips:So the previous idea was, so me and my brother, Dylan had this Facebook page that grew to almost a million followers on Facebook. And it was a meme page. It was just, you know, funny memes. And, you know, in this process of trying to turn that page into a business realized, you know, for a large social page, you know, with a lot of engagement around memes, like how do you turn that into a business? And so I just kind of was like researching that and meeting other founders in that kind of space and ultimately realized like, oh, you know, building a content company is how these, you know, people monetize these big audiences.
27:12David J. Phillips:And so we kind of built like this BuzzFeed clone. And in the process of building that business, you know, learned all about distribution for listicle websites. and, you know, it was a whole underground business of link sharing across all these large pages. And it was like, you know, spreadsheets and DMs and, you know, it was totally a bit chaotic. And so the idea for Bloomjoy was like, let's automate all of that for all these pages with large audiences. And it was all mostly Facebook pages at the time. And so, you know, had about a year of experience in that problem was excited about it and like wanted to build this marketing platform to help these Facebook pages, like build a business and make more money.
27:57David J. Phillips:And, um, you know, that was, it was a little bit shallow, I guess, across all of my experience of like this one domain that I was recently learning about. And, um, yeah, I mean, it worked out for a little bit, but then, you know, Facebook changed their, their terms of service. You couldn't really do this like above board anymore. And it just like killed the whole business. And so yeah, fast forwarding to Fondo was like, you know, part of that filtering process is like, yeah, what's a enduring business too, right? Like what's not going to be killed because, you know, some terms of service are going to change.
28:34David J. Phillips:I mean, now there's all sorts of other risks, but yeah. It reminds me a little bit of like, you know, solo founder Jeff Bezos thing where he says like, what a lot of people look at what's um what's changing and he likes to look at like what's going to stay the same right people are always going to want lower prices yeah they're always going to want faster delivery right right things like that and it's like well people are always going to need to do accounting uh for for their startup it's good the way the way the way it is it's going to look different over time of course maybe cloud will be doing it all yeah but like there but there there's it is a thing that is going to happen um and it's going to continue to be a need in some form factor or another um something that also kind of strikes me about what you were saying about sort of the original product versus Fondo is it not just that sort of like enduring need but also one of them the first one felt like it's sort of an emergent learning like an emergent insight um and uh somewhat of an opportunistic move uh versus Fondo felt like more of a sort of an ongoing sort of like enduring insight into who you were like the things you were interested in the things that maybe you had like a more of a long-term sort of unique point of view um and it feels like fonda was sort of this combination of you had this sort of industry background but then also you had the startup understanding of like what do startups actually need right so it's not just saying um hey i'm coming from this other industry and i'm trying to do startups.
30:04It's like you combine those two things and that feels like what makes Fondo special.
30:09David J. Phillips:Yeah, I think that's right. I think it's sort of the culmination of everything that I've been really immersed in for the past, you know, almost 20 years. So yeah, it really just made sense. So I think that that's a really interesting takeaway for people who are maybe listening to this and thinking about like what are the things that I should be working on if they're sort of in the idea base or if they're working on something and they're like maybe it's not working or maybe there's a shelf life to it similar like the terms of service stuff with Facebook maybe it's about looking at like what are these things that are kind of things that you've kind of accumulated throughout it doesn't matter how old you are right?
30:51Totally. The things you've accumulated throughout your life could ultimately inform kind of the thing that you're best suited to work on.
30:59David J. Phillips:you know, all everything, you know, when you're building a startup, you are starting from nothing, right? And you want to build trust with your prospects, right? And the best way to build trust is adding value, right? And the best way to add value is to be an expert at whatever you're selling. And so, yeah, thinking about like, what are you an expert in? Where can you add value and build trust to create an opening for people to buy your product? That's cool. One thing that's really interesting is your relationship with your siblings and working with working with siblings. And it's not really discussed that often, you know, working with family members.
31:39But it seems to be something that's gone really, really well for you. And every time I meet the Fondo team, not just not just ones that you're related to, but like everyone, it feels like this really, really great culture. But maybe you could speak a little bit about kind of, you know, working with working with siblings.
31:57David J. Phillips:Yeah, definitely. I think, you know, it's kind of related to just, you know, in some ways to solo founding, right? I mean, when you're when you start a company with a co-founder, you know, you have a, you know, someone that you're building with that you can really trust that has, you know, skin in the game. And there's a lot of good things about that, right? There's, there's, you know, when it goes right, that's really good. I think family, you kind of have that already baked in and you can have a complete falling out with a family member, but it's less likely to happen than with a co-founder.
32:36David J. Phillips:So you kind of, I think there's a lot of great things that come along with working with family in the sense of trust and loyalty and, you know, giving a shit, you know, wanting the company to succeed, things that are great to have in team members. So, you know, if you can work well with your family, it's a great thing. There's, of course, all sorts of other, you know, things that can go wrong, right? And, you know, you gotta, yeah, you have to be open, you have to have your, like, pretty, be pretty clear about, you know, know, what can go right and what can go wrong and try to, you know, set expectations with each other and try to work as, you know, professionally as you can, even though you're siblings.
33:24David J. Phillips:Yeah. In terms of, in terms of Fondo, I think there's, there's a really interesting story about how you got your first users. So maybe you can share a little bit about that, sort of what that like initial sort of, I wouldn't call it necessarily a breakout moment, but like this sort of, this thing that kind of got went from like okay you have this idea for the product you have um you're working with a few people and then it's just sort of like you had you had this one move that you did that kind of like caused it to really really pick up uh steam i think would be really useful and interesting to hear that story uh and then maybe talk about sort of like how you thought about going from that sort of early sort of um hatchling stage to like you know building out like a bigger business?
34:05David J. Phillips:Yeah. So yeah, so when we, you know, we emailed our investors and said, you know, or I emailed our investors and said, you know, I'm going to try this idea Fondo. And it's going to be, you know, we're gonna do bookkeeping for startups. And, you know, I had varying responses from different investors. You know, like I said, I had some investors are really supportive. And then, you know, I had one investor was like, hey, I want to cancel my safe so I could take a loss this year. Like, how do we do that? And, you know, another investor was like, you know, Atrium had just imploded. Like, hey, this is a really bad idea.
34:40David J. Phillips:Like, look what just happened to Atrium. So, you know, I was still feeling pretty good about the idea, but I was, you know, I was like, where am I gonna get my first customer? So, you know, of course I went to Twitter and, you know, someone who I'd followed on Twitter had been asking about like, hey, who's everyone using for bookkeeping? I need somebody new. And so like when, you know, this was Sam, I'm the founder of The Hustle. So I messaged him. Yeah, Sam Parr. He, one of our investors, Chris was also an investor in The Hustle. And I was like, put in a good word, please. And so, you know, we had a good word put in for us and then went through this whole sales process, like got The Hustle.
35:15David J. Phillips:And I was like, okay, this is it. This is the business model. Like, you know, we're making, you know, six grand a month. We just need, you know, 15 more of these. and, you know, we'll get to, you know, 1 million ARR and it's great. Like, let's go close them. And then started going to all my other friends, startups and, uh, and nobody was signing up. I thought like, man, we figured it out. Um, and no one signed up for like three months. Like all my friends, I had a bunch of friends and startups that already had bookkeepers or, you know, uh, actually chose a competitor over us because we were so new.
35:50David J. Phillips:And, um, you know, this was kind of like for mid-market companies. Uh, and I thought, Oh man, this is, this is, I don't need 15 more customers. I need like, uh, we need to go like find earlier stage companies that need this. And, um, it's going to be way less revenue and we need way more of them. And, um, so it was a pretty, you know, pretty dark three months of, you know, was this going to work or not? Um, and we were just doing bookkeeping at the time. And then, um, you know, one of my friends was telling me how annoyed they were by like Delaware franchise tax and how complicated the Delaware, you know, the, the system was for like getting that filed and how confusing it was.
36:30David J. Phillips:And so I started looking into it. I was like, oh, this is actually a really interesting wedge. You know this is probably really painful for a lot of other founders. And so, you know, did a post on book face and was like, you know, who needs help with Delaware franchise tax and got a bunch of people interested and basically offered to file it for free. And we got like 100 companies to sign up for that. And, you know, did, you know, learned a lot about Delaware Franchise Tax during that time. And yeah, filed 100 Delaware Franchise Tax returns and then pitched those 100 people on bookkeeping. And that's how we got like our first 10 customers.
37:08That's amazing.
37:09David J. Phillips:So you kind of almost offer this like mini product that people could use that makes it so that they can build trust with you, like experience what it is like to work with you. And then once they have a really positive experience, why wouldn't they work with you? Right. That's really cool. Is there anything that you've done in the past that was quite like that? Or was that sort of like a new concept for you, this idea of like building almost like a mini product that kind of feeds into the main one? It definitely happened earlier on, you know, when I started the coding bootcamp Hackbright, we volunteered at like, well, first we launched on Hacker News and we got like one applicant.
37:50David J. Phillips:We were on like the front page of Hacker News and got like one applicant. And so that was extremely demoralizing. It was one of those, you know, reminders, like if you build it, they won't come. And so just was thinking like, how do we get, yeah, how do we get people to like buy the thing that we made and how do we build trust. And so we started volunteering at like local meetup groups and like teaching code for free. Um, and that's how we got our first users was like doing something, you know, related to what we're selling for free, uh, building a reputation, building trust, and then, uh, offering, you know, putting our offering in front of everybody.
38:26David J. Phillips:And so, uh, that's how we got our first customers at Hackbrite. Um, yeah. So I think that was when I really learned like, yeah, you need to, uh, you need to build trust and the best way to build trust is adding value. And, uh, you know, the best way to get people to let you help them is to do it for free. That's really cool. I mean, I think the other thing that kind of comes to mind is sort of this like mini products or like things that are free value, um, that you can give to people that really are helpful and meaningful. Um, the hack break example is great. Um, the, the Delaware franchise tax is great but other one is you know you're doing a lot of media stuff and uh the media stuff is really interesting because um you're like wait why why is fondo doing like a live stream tv show why does fondo have this like this major like news publication that you're that you're working on um it feels like a lot of that is just like it's good to do this stuff for the industry um you're not trying to only highlight fondo customers or something like that but you have an audience you have a reach um you are able to get what people are doing in front of more people in the industry like that's a positive thing it's it's different than sort of like the the thing you're doing with hackbrite was directly related to you know getting people to to do the the the school like the full-time school it's different than the delaware franchise tax which is like you're doing a you know a tax related thing for people to help them then get into the bookkeeping but I think it's like I think it's got something really powerful so maybe you can say a little bit more about just how you think about like helping the ecosystem and supporting the ecosystem because I think I think it's a really good thing I think like more startups could do things around this yeah I think um you know ultimately the purpose of most companies is to help people right help solve a problem.
40:21David J. Phillips:And when you think about your users, they're not necessarily always thinking about how your product solves their problem. They have tons of problems, right? And it, you know, there's arguments like why, why waste your time helping people with the problem that's completely unrelated to your product. But I think that when you help people and you build trust, you're going to create an opportunity for them to consider your product, right? And that's an opportunity that you don't get if you don't do this thing, right? And so it's totally, it's super valuable to help your customers and your prospects in ways that are not related to your product, to build that trust and build that, yeah, build your brand, right?
41:07David J. Phillips:And so, you know, we target early stage companies, you know, and early stage companies have a lot of problems that they're trying to solve. And the biggest one is getting customers and getting people to know about their products. And so we built an audience over the years and we thought like, okay, we can help our customers. We can help our prospects win by using this asset that we have. So like, let's do it. And so that's kind of how the idea started. We started out with our blog and featuring founders on our blog. And then, yeah, then we decided to try it with the podcast. What have you learned from sort of helping elevate founders?
41:44It's such a good idea because ultimately, you know, people need to hear about bookkeeping and accounting, like they need to hear about these things. It's really important. It's sort of like a necessary thing, right? But at the same time, you know, like having people hear about Fondo through just great things that you're doing for the ecosystem makes it so that they're not only hearing about you through sort of like, oh man, I have to figure out this Delaware franchise, which is great because like you actually are a godsend to people in that regard. Um, but maybe, yeah, what, what are some of the reflections, uh, after having sort of worked on this stuff to like lift up people in the ecosystem and promote other people?
42:22David J. Phillips:Yeah, I think, um, you know, I think people really appreciate it. I think people are sometimes scratching their head, like, why are you doing this? Um, but, uh, And yeah, I mean, I think people are surprised and it's been amazing to hear the stories from founders who, you know, we've had a company, you know, that ended up getting acquired after being on the podcast or companies, you know, raising, you know, getting a check from an investor or, you know, going to an investor meeting with someone who just like, oh, I just saw you on the Fondo stream. um so yeah it's kind of creating opportunities for people in in this sort of fun way um where yeah i mean this the the journey can be such a grind and so like creating this you know just you know coming on the stream for like 15 minutes 10 15 minutes is creating opportunity for them to help their company succeed and um yeah that's pretty incredible so we always end the podcast with three questions.
43:18The first question is the bear case for being a solo founder. Why you shouldn't do it. The things that you feel like are particularly bad about being a solo founder or challenging about being a solo founder. And we'll let you respond to that. We'll probably have a talk back and forth about that a little bit. And then we'll ask the next question, which is, of course, the case for solo founding. and then of course we'll uh we'll have the the third question to be a little bit of a surprise all right i like it but what's what's the bear case for solo founding the bear case is it's
43:52David J. Phillips:just really hard it's really hard to start a company and make it successful and it's even harder alone um and um it's just really hard why why make it harder say more about like the things that were difficult i mean you had you had a sort of a special situation here in that you'd raised a million dollars. You had, you know, you'd already like spent 99 % of it. You had people who were not necessarily investors. They were investors, but they were not investors in what you're about to turn the company into. So it was kind of like they were along for the ride. So like there were some aspects of this where it was like a little bit different than solo founding in general.
44:34But say more about sort of the difficulties and the challenges there.
44:39David J. Phillips:you know when you launch and no one signs up you know who are you going to commiserate with when you are stuck and can't solve something like who are you going to bounce the idea off of you know when things are going great when you launch and a lot of people sign up it's great you know but when things go bad which happens like 99 of the time you know having a a partner on the journey just makes it slightly less hard. Okay. So now we're going now that that's sounded pretty dire. It does not, it does not, it definitely doesn't sugarcoat it. I will say that one person said that the, the, the toughest part, or what do they think about when they think about solo founding?
45:22He described it as crying during the middle of the day and having no one to talk to about it, which seems to attract. Let's talk about the case for solo founding. What is the case for solo founding?
45:35David J. Phillips:Man, well, if you can get through those moments, like it creates this like pretty incredible resiliency. Do things on hard mode. I mean, why should you do it? Why should you make it any easier for yourself? You'll learn more when it's harder. You learn how to build a team earlier. You, you create, you learn how to build a system that helps you with that resiliency, whether that's, you know, in your personal life or through building your team at your company, you can, you know, give people more equity when they join you in the journey. You can, yeah, you can have this like incredible founding team and you can have this like frictionless experience bringing your ideas to market really early.
46:25David J. Phillips:And, you know, the lows may be a little bit lower, but you just learn so much from that and you become, you know, even more resourceful, right? And like to be a successful founder, you have to be like relentlessly resourceful. And I think when you're a solo founder, you're just forced to be even more resourceful. Yeah. you have no option when you have no team especially you have no option you have to be you have to be at like the buck stops with you um and i think that's really that's really important and worth mentioning that's really helpful to share with people um the last question is usually imagine that we we just stopped recording right now we hit we hit the end of the recording button uh we say oh that was really fun and then and then uh and then 30 seconds later there's this realization that, oh man, we should have talked about this specifically as it relates to solo founding or your experience with solo founding.
47:21Like what is that thing that if we had hit stop and, uh, and, and we sort of like, we're standing up, we're like, oh damn, like what, what does
47:29David J. Phillips:that think, what does that think we should have, we should be covering right now? I think, um, you know, we haven't really talked a ton about, you know, what starting a company today looks like, right? So a lot of my founding experience has been, you know, has been over many years. And I think today it's even more different, right? And there's even more of a bull case for solo founding today. You know, everyone has a co-founder like in their pocket now, you know, with Claude or ChatGPT, you know, like building has become so so, so much more possible, like bringing things to market can happen so much faster.
48:13David J. Phillips:And yeah, the so there's a lot of, yeah, there's a lot of, a lot of momentum towards just starting, right? Because there's a lot of times people don't start because they're waiting for a co founder or someone tells them they need a co founder. But that's not the case anymore, right? That's awesome. So maybe say maybe say a tiny bit more about that. So like, Like, so people shouldn't necessarily wait around. There's this more of a reason to get started than ever before. What about that excites you? What about that makes you think that maybe we're going to see sort of this sea change? I mean, you know why we're doing solo founders is because we believe that now more than ever, solo founding is possible.
48:56And also, like, by the way, at some point, solo founding should flip and it should actually be the default. like I think that you and I both agree that like great like truly great co-founders are awesome but at the same time if you have default co-founder that leads to a lot of really bad co-founders totally so maybe say a little bit more about kind of how you think about that that shift happening and the positives there yeah I mean I think default co-founders happen
49:24David J. Phillips:when you don't want to do the hard thing right like it's harder to go alone and I think it's becoming less hard, you know, I think there's, um, there's more reason to pick the harder path because there's things that are happening that make it easier, right? Like, you know, uh, Claude Code and like Cursor and like, um, like you can, you can build things really fast. Um, solo, you don't need a co-founder to build, uh, build things really fast. I mean, of course, if you have a great co-founder, you can, yeah, you can go, you can go pretty fast. But, um, you know, I think in the past it was like, you know, just to get an MVP, I need a co-founder, you know, but now like anyone can build an MVP and you can get customers.
50:11David J. Phillips:Like there's, um, you know, there's always, it's funny because there's always people who see something become really popular, you know, or like, you know, um, see, uh, a company. I remember when Uber came out, I was like, oh, I had that idea, you know I should have done that and um now you can literally do any idea that you want there's no excuse um you know I should have done that but I didn't have a co-founder I didn't know how to code um you know there's no excuse like you can build anything um and if you can't figure out how to build anything um it's going to be really hard to build a company so um so go solo yeah yeah the The water is really going out for the people who are idea guys.
50:54You know, like they have no excuse anymore.
50:57David J. Phillips:Exactly. Awesome, man. This has been great. Thank you so much for doing this. Thank you so much for having me. Yeah. If you enjoyed this conversation, we would love it if you could share solo founders with everyone you know, particularly people who are considering starting companies solo or who are already doing it. You know, the entire goal of what we do is to normalize solo founding, encourage more people to solo found instead of end up with co-founders of convenience. If you'd like, and we'd really appreciate it, you can go leave a review on Apple. You can go give us a thumbs up. You can subscribe on the YouTube channel.
51:26Anything helps. And of course, if you are starting a company or considering starting a company, you should go look at the Solo Founders Program. We work together with you in San Francisco alongside of a bunch of other solo founders. The idea is it's much better to be solo together than to be solo alone. I'll spend a lot of time helping you. And we also invest$100 ,000 in your company. So if you're excited to learn more about that, go check out solofounders.com slash program.
From the publisher
David J. Phillips tried co-founders four times before he went solo. With $40,000 left in the bank after a stalled aquihire, he refounded the company alone — and built Fondo, the accounting platform now used by hundreds of YC and pre-seed startups. The conversation is part founder-confessional, part early-stage GTM playbook.
Topics covered:
- The four co-founder breakups across four prior startups
- Refounding with $40K and a single investor email
- The lived playbook for co-founder breakups (lawyer advice, severance + stock + move on)
- The four-question $40K filter for picking ideas you can ship solo
- The Sam Parr false bottom — first customer, three months of nothing
- The Delaware-franchise-tax mini-product wedge that produced the first ten paying customers
- Bear case and bull case for solo founding
- "Your co-founder lives in Claude now" — the closing argument
Guest: David J. Phillips — founder & CEO of Fondo, the accounting and tax platform for venture-backed startups.




