In this round‑table episode, a group of SaaS founders—including Andrew Gazdecki and several unnamed speakers—reflect on the most valuable lessons they wish they could give their 25‑year‑old selves. The conversation covers a range of themes: the importance of embracing failure and learning quickly, adopting a planning rhythm of short‑term 6‑week sprints balanced with a 60‑year vision, launching side‑hustles early to gain financial independence, and treating entrepreneurship as a lifelong career rather than a one‑off event. Speakers also draw parallels between good software design and solid business architecture, emphasize the need for patience and long‑term brand building over chasing rapid billion‑dollar exits, and stress the significance of family and personal moments amidst the founder grind. The episode concludes with a promotional sign‑off for Horizon Capital.
Chapters
Yeah, Matt, what's, uh, you know, one piece of advice you wish you had known and would tell your maybe say 25-year-old self today based on what you know today?
Yeah, you know, it's funny. I think, you know, I'm— it's funny because this is— I don't think there's— I think this is a really strange question, and the reason I say is I think that you actually— it doesn't matter what you say to a 25-year-old, they're still going to make all the mistakes.
That's right.
Like, you have to fail and then reflect in order to grow. And the question, I guess, the question is how fast can you fail and how quickly can you grow, right? So, and I guess what took me forever to get over was fear of failing. I would almost like rather not try or like put the bar so low. So that I was sure, because I was just so fearful of failing in front of my peers, in front of my, you know, I don't know, in front of my bosses, in front of, you know, investors, in front of like, you know, and that, like, getting over that was so important. And so maybe that would be something like, don't be afraid to fail. Although, you know, and I think it's changing. I think people are realizing how, you know, it's very different when I was growing, coming up at JP Morgan, which was like— Do not fail. If you fail, if you make a mistake, you're out. That was literally the culture of JPMorgan. It's better to make no decision than it is to make the wrong decision, literally. That's the opposite of what we're trying to do here at Summa. It's like, we're going to make mistakes. Let's make a decision. We don't have perfect information. We've got to do it. The quicker we make the decision, the quicker we execute, the quicker we can make a mistake, the quicker we can learn. We've got to always be learning, always be learning. That's probably what I would've told myself if I were— If I could go back in 25 years.
Do not have plans for 2 years, 3 years. My biggest learning was either to plan for 6 weeks or 60 years, nothing in between. And planning for 6 weeks had been working great for anything that I have done— building products, building teams, trying out new marketing ideas. 6 weeks is kind of the sweet spot that I figured out myself. Not quarter, not month, 6 weeks. Either plan for 6 weeks or 60 years, nothing in between. Keep an eye on the bigger picture and then do small, small incremental stuff in 6 weeks.
Start a side hustle as quickly as possible. Start with service. So start selling something online, your skills, or even something you don't know and that you would train yourself. But just make that first money online just so you understand that you can be free and that you don't have to be an employee if you don't want to. And that this There is another path for you to be free and to make your own money. Because I felt for me that when I had this kind of like switch mindset, it opened up so many doors.
Okay.
So my conception, I think, of entrepreneurship when I was younger was that entrepreneurship is a moment in time. You build a business and it happens, right? I think I've come to the realization recently that entrepreneurship is way more like a career. And in like any other job, right, like you take learnings from one to the other. And multiple-time founders have experience in founding, right, that, that pays dividends. So I, I sort of have, um, many different types of ventures that I have been working on, right? So, uh, my wife runs a cocktail ingredient company that is called Pratt Standard. That's right, cocktails. Uh, it is a, uh, it is very much like a product-based business, right? And so like you fill bottles, you sell them to people, they like them, they rebuy. There's a cost of inventory, there's a cost of production. Um, you know, it's very traditional in terms of like your cost and finances, right? We run a service business, right? And so we've got people, people have hours, there's an hourly rate, there's billability, there's sort of all that stuff that revolves around our finances. Aspire was a venture-backed company, right? We raised a lot of money, we spent it down, we raised our next round of money, we spent it down, right? And our goal was valuation increase. That's what we were thinking about day in and day out. Um, you know, prior to that at EverFi, right, it was like very much like a high-growth, high-growth tech company, um, but they had this huge profitability element, right, that they were thinking about. And so there was sort of this hybrid of the two. 80% of all those things are the same, right? We get really anchored around the differences between these things, but most of them involve being a good leader, organizing people, being responsible, following through on things, these sort of principles that apply over and over. And I think seeing that set of values in many different environments is what progresses you as an entrepreneur. And so, yeah, I guess my advice to my 25-year-old self would be like, don't think of this as like a one-shot thing. Think of this as like You're going to be doing this for 30 years. Part of the entrepreneurial journey is going to be growing and developing and learning yourself. So don't hold any one thing too tightly and expect this to go on for a very long time and kind of think about your career arc like that. And I think now I'm starting to do that in a way that I didn't before. And I think it's been a lot more fulfilling and rewarding.
I never thought about it that way, like putting entrepreneur as a job. People are so against the idea of calling it a role over a title. But it makes sense. You're an engineer. You start off by doing basic stuff, and then you build your way up and you get better, then you become a senior engineer, and, you know, then you become manager and whatever, director. And I mean, that's the same way with entrepreneurship. By having your first few ventures, you get better and better. And I mean, you have to refine those skills that come with being an entrepreneur, right? Which, yeah, I think, yeah, that's a really good way.
I think it's very similar. I think I said this before, but there's so many similarities, I think, between good code design and good business design, you know. Um, and, you know, modularity, scalability, all that stuff kind of plays in both worlds. I think that, like, this idea of abstracting up a level and sort of building principles that are sort of, like, not language-dependent or code-dependent has a parallel in the business world, right, where you see these patterns play themselves out over and over. I have a great business mentor, his name is Tom Raffa, and he says that he basically sees the same 30 issues play out over and over and over again, right? And once he's done things for many different times, right, he sees those issues and he knows how to handle them because he's seen them in so many different environments. It is funny if you kind of think about boiling down a lot of code, you see the same 30 issues over and over. You boil down a business, you do see those issues kind of play out. And so I think without experience, it's very hard to identify those things. And some people can do it, and those people are way smarter than I am, right? But I needed to see those things play out 2 or 3 times and experiment with them and try them to be able to kind of identify those things, right? And move forward with them.
Like, for example, after I sold Altcoin, I had no idea what I was going to do, and it kind of freaked me out. I didn't have any business ideas. I started kind of Mulinga and MicroQuire. Then I took a CRO role at Spiff where I managed their sales team and marketing team, just because I didn't have a startup idea and I was playing Madden all the time. I became the number 98 top Madden player. It was getting— my wife was like, you need to just start a company or get a job. And I was going to be an advisor at this company called Spiff. Look Spiff up. They're badass and they're— that whole team is amazing, but they automate commissions for large sales teams. I'd used their competitor, so totally fit. But my CEO coach just said, Andrew, just calm down. Like, you know, let opportunities come to you and don't just jump on the first thing.
Yeah.
And this can apply to acquisitions, this can apply to jobs, this can apply to startup ideas. when something really special comes along, you just kind of feel it. And I can also apply that thinking towards Microquire as well, where I have a journal entry that says, and I've shared this publicly on Twitter if you dig, where I wrote in December 2019 before I launched it, like, I don't know if this is going to work, but I think it should exist and it looks really cool. And it worked. But my point is, you know, keep shooting shots. Understand you might miss a few, but just, you know, keep getting up, but don't force things. And so with MicroAcquire, I didn't force it. I just loved it. I kept going. I was consistent. And over time, the brand built. People started actually acquiring businesses. So I guess another way to put this would be to think long-term. Like, it took me 9 years to build Business Apps, and I think a lot of entrepreneurs are trying to build businesses in like a year and become like a billion— like a billionaire or something. Like, it rarely works out like that.
Yeah, that's your arch nemesis, the TechCrunches of the world, right?
That's why you built the Bootstrappers.
Yeah. And then in terms of like family, you know, family's everything, like everything. Like my wife's my biggest supporter. My son's first word was poop. Yeah, it was kind of funny. He started pointing at my dogs like poop. He's like poop, poop, poop. But just don't miss out on those special moments. Like if you're building a company, because it's so easy to get like 5 AM, you're working all day. But, you know, don't, don't miss out on like the opportunities that like you can't get back.
Thank you all for listening in to this episode and joining SaaS District today. Don't forget to leave a review and subscribe for future episodes where we interview top leaders in the SaaS industry. If you're a SaaS company looking to grow and unlock the true value of your business, get in touch with us at horizoncapital.com, and myself or one of our consultants will provide a free assessment to help you get there and hit your goals. If you have any feedback or suggestions for this podcast, please DM us on Instagram or LinkedIn @HorizonCapital and help us improve our content for you all. Thanks again, and hope to see you on the next one.
