Alex Hawkinson, who successfully sold a company to Samsung for $200M. Watch the full video — free, no account needed.
This video features Alex Hawkinson, who successfully sold a company to Samsung for $200M. He discusses his entrepreneurial journey, including bootstrapping and fundraising strategies for his new venture, BrightAI, which aims to automate infrastructure with AI.
You should work on the most important problem that you can imagine even though it seems harder. Why? Because the best people want to work on really important problems. The best capital, the best investors want to invest in really important problems, right? And the biggest businesses that exist in the world that go out and create the maximum amount of wealth and impact and other things often are businesses that solve like really fundamental problems. All righty. Hello everyone and welcome to the Dealmaker Show. So today we have a founder that has started so many companies that I got dizzy. I mean a lot and we're talking about a lot but also a lot with success, you know, several of them, you know, with exits, you know, with great exits. And again, today we're going to be talking about focusing on the right problem. thinking about bootstrapping versus raising money. Uh what, you know, may
cause the switch from, you know, tackling one industry versus another. Uh and a lot of good stuff, you know, that has to do about the building, the scaling, the financing, the exiting, all of those type of topics that we like to cover. Uh but again, brace yourself for a very inspiring conversation today. And without further ado, let's welcome our guest today, Alex Hawinson. Welcome to the show. >> Hey, thanks for having me. Uh big fan and excited to be here. So, originally born and raised in Minnesota, but the family from Sweden, you know, quite the entrepreneurial origins that you had. So, Alex, give us a walk through memory lane. How was life growing up for you? >> Cold and dark in Minnesota. No, it was uh you know, my uh I think like waves of immigration across the US. just my relatives like immigrated to to Minnesota from Norway and Sweden and uh grew up with a family of
entrepreneurs like had a pretty lucky life in a lot of respects. But if you don't know about Minnesota, it gets deeply cold in the winter. So I was excited as an adult to toh get out of there. But grew up uh grew up again in a family of entrepreneurs learning at the dinner table. You sort of don't uh you don't go get jobs, you have to make them. And uh you know uh everything started from there. >> So obviously for you after Carnegie Melon you know getting your degree you know it was creating your own job you know and that was the first company which was infrepneur. How do you how do you enter the venture world? How was that for you? >> I mean for me it was uh you know just always been somebody that I love. I'm a very curious learner and so I like to go down rabbit holes and to see where it leads me. Uh so I I was lucky you know when I graduated from CMU I had uh you know
programming experience and other things but the internet was just emerging and so I started uh tinkering building websites on the side which nobody knew how to do. It was the kind of wild west of the early internet days and uh one thing led to another. I had sort of friends ask me how do I do it and then eventually businesses asking me to help them in building sites and then eventually web applications and those things and so um built the business up and it was acquired as part of a rollup of a much larger business but my early early career days you know just happened to coincide with the emergence of one of the biggest technology enablers of our time. So then from there you went to Optics and Optics was a spin out uh company. I guess that there in in optics you know the the most incredible thing you know that happened in terms of lessons learned is really figuring out how to focus you
know and to have a great team to focus on the right problem. So tell us a bit more about this >> second one of the second stages in the internet was you know people thought okay instead of having applications that we host on a server inside of the four walls of a business. It seems so obvious now but you'll host them outside but it wasn't SAS yet. So these were desktop applications that you would basically host in the cloud and and otherwise. And um Aptics became the biggest in its space. It was providing hosted like email and messaging and calendaring and things for small businesses and uh it was just even though it was successful it was a really challenging business and why because you know are you solving an important enough problem? I mean, does if you're a small business owner, I mean, I'll ask you like, do you wake up and think about hosted messaging every day? Like, no. No.
The answer is no. You think about how to find customers, how to service customers, like what's your product, those things. And so, Aptics was a great it was a great experience and we had a good, you know, success in the company. But I really I started to feel this this need like you know if you even if you have a great team which I have there if you focus them on a problem that's not meaningful it's like you can you can manage to push the boulder up the hill but as I'll talk through later experiences if you pick the right problem with a great team like it feels a million times easier because the right people the right capital all the things want to happen you know for the right right right type of business problem. So you eventually ended up leaving optics and the next thing you know was SMB life you know which was the next company that that you started now with SMB live that was quite
the bootstrapped journey. So tell us about what you were doing at SMB live and why bootstrapping the operation versus raising BC money. I mean, so what SMB Lab was doing is trying to slab the slightly more important problem than Aptics was, but it was uh helping small businesses connect with cons uh with customers uh on the web. So if you're familiar with HubSpot, you know, today they've become a massive company. It was sort of in that in that zone. I um you know I had had a lot of experience from both US web who acquired my first business and then from optics and sort of investor relationship management and those things and about the sensitivity to like you know you shouldn't raise my attitude is you shouldn't raise money before you really know the pattern in a business like once you've got product market fit or you really understand you know exactly the repeatable pattern in what
you're doing even if you can raise money before that I think It's a mistake because you end up you end up at odds with the investor. It creates all sorts of of pressures and uh this was further reinforced when we'll go to you know later stages with smart things and and brightey etc. But um so yeah at SMB live you know learned you bootstrap you have total control all the way. We did find product park product market fit. We had an exit. We are acquired by a great company called reach local. And uh the beauty in bootstrapping is even if it's not as massive of an exit uh you the the people that founded it, you can still have a really meaningful outcome on that front. But I think the biggest takeaway is again you don't raise outside money until you know the market pattern that you really want to go and solve um you know completely or you're going to end up in a tense situation. and and I
guess second acquisition, you know, what at this point, you know, what would you say you had learned about the acquisition process and and getting a good deal done? >> Oh man. Uh there's a lot of things there that continue to unfold in later stages, too. I mean, I think in the early ones, I was just like happy to have the money, you know, as a young young guy. you you um I you know in all of them it's really it's less the acquisition and more what happens afterwards you know that that that matters on different fronts. I mean obviously it's great as an entrepreneur to have liquidity and have an outcome uh in a business but uh you got to be mindful obviously of who you're who you're joining forces you know with and realizing like your ability to control the destiny of the company is effectively gone you know the second you go through this acquisition process so um you know but I
think what I learned in the beginning is like wow it's really nice in life to have a little bit of liquidity stupid as that sounds lets you do a lot of things like take bolder risks down the line you know if you can have >> well I mean since you're talking about liquidity what was the first thing that you bought you know when >> that liquidity hits the bank >> I think I paid off my mortgage you know that was like the thing I I tend to hate banks not nothing broadly against them but you know I uh I think that was the thing that felt the best so you know >> so I know that >> well that's good but look I think that nothing feels better than you know being on stepping up on the green grass. You know, it feels greener when that mortgage is gone. So, I can I can totally see that. Now, in your case, um you know, at that point, you were starting to form a family,
having young kids…