The Smartest Guy in the Room Still Had to Start Over
A conversation with Andrew Ackerman
Andrew Ackerman has been a consultant, founder, the investor, and now, author. From corporate boardrooms in London to the war rooms of New York tech startups, he’s seen every side of the table—and rebuilt himself at least four times along the way. As the former managing director of Dreamit Ventures and a relentless builder of innovation platforms, Andrew has backed over 70 startups, shaped industry verticals, and pioneered investor sprints long before venture capital found his playbook. But his most compelling work may be what he’s architecting now: a new kind of fund, forged in hard-earned pattern recognition. In this Unscripted, Andrew talks with me about walking away from a nearly signed deal, why “planning” is overrated, and the unexpected clarity that can only come from starting from scratch.
His new book is The Entrepreneur's Odyssey.
1. What was the moment you knew the old life wasn’t working?
There were a few times.
I started my career as a consultant for Fortune 100 companies. They were smart, interesting people to work with, but large corporations are slow to change. I was on a project back in 1999 in London helping BP as part of a merger process. We had built an intranet application that allowed the two organizations to share data on headcount and expenses without the other organization seeing the raw data… which would have been a big problem if the merger didn't go through. I was already ambivalent about working as a consultant for large corporations, but then when I saw this, I knew that that was where I wanted to go instead.
The second time was after my second startup. My first startup had been reasonably successful, but the second one devolved into founder drama and ultimately into lawsuits. I was interested in doing another startup and almost did, but I was a little bit trapped in the almost successful enough limbo: if you're very successful, getting backing for another startup is easy, and if you've never tried to start up before, you can still sell the dream. But hitting a double is sometimes harder than never having been at bat in the first place. At the same time, I had made a few angel investments and two of them did well very quickly, so I started to think more and more about moving to the other side of the table, eventually landing in charge of Dreamit’s NY accelerator program.
I'm currently thinking through whether I want to do another career course adjustment. I've been investing for the past 7 years in proptech and construction tech and love the space. So there are a few firms that I've worked with for a while where I could come in at the right level, but that's very much dependent on whether they're able to raise their next funds as anticipated.
At the same time, I'm a huge believer in platform-based investing, having operated, built, or consulted for dozens of accelerator, incubator, venture studio, and corporate innovation platforms. I've been developing an entirely new fund concept and have been talking to the right kind of partners that would make that platform work. I've changed industries before, so that doesn't faze me. The tricky part is, for the platform to work, it has to be a very specific kind of partner, and there aren't that many companies that qualify. So stay tuned.
2. What did you have to give up—internally or externally—to pivot?
I've changed from consultant to founder, and then from founder to generalist investor, and then to EdTech investor, and then to proptech and construction tech investor.
Moving from one of the big consultant firms to founding a company meant the usual sacrifices: getting used to doing everything for yourself because there were no other departments to do it for you, giving up a relatively comfortable salary—I went over a year entirely without salary at my first startup when we needed to.
Founder to investor was a much smoother transition. I had to give up the joy of going knuckles-deep into the minutiae of the company and learn how to keep my attention at the appropriate level so that I could give actionable advice but not step on the founder's toes.
Moving from generalist to sector-specific, I was afraid that I would miss the variety. But it turns out that once I drove deep within EdTech, there were plenty of innovative startups to keep me from getting bored.
EdTech to proptech and construction tech was a more wrenching transition. I walked away from large parts of my network of fellow investors who simply were no longer relevant (still keep in touch with some of them, but it's not the same), and the reputation we had that helped us source great startups didn't really transfer over to new sectors, so we were basically starting from scratch with relationships and reputation. But the opportunity was so big and so relatively untapped that we had to do it.
3. What’s one belief you no longer hold that once defined you?
I used to feel very strongly that people need to be responsible for planning their own futures, but I've come to see the role that luck can play in things, making it very hard to plan over long periods of time with any certainty. So I've become more sympathetic to people who don't have a good plan or whose plans have become derailed. As the old Yiddish expression goes, “Man plans, God laughs.”
4. What’s your definition of a good summer?
Kids away at camp for about 2/3 of it. Plenty of time to spend with them, and even more time to spend with other adults, kid-free, at the beach/lake/Hamptons. Lol.
5. What’s a decision you made recently that scared you—but you did it anyway?
I went pretty far down the road with a fund that I was going to join as a founding partner. I really liked the platform we were going to build, and I had started to line up investors from my network. But as we got closer to pulling the trigger, I didn't like the way the founding partner was handling things, and I ultimately pulled out. I burned the better part of a year on that startup, and I was concerned about the reputational effects of switching directions, but I've learned not to ignore my gut on these things.
6. What’s your relationship with failure now?
It's not a failure if something doesn't work out. It's a failure if, looking back on it, you can say that—knowing only what you knew at the time—you should have known better or made a different decision.
To use a blackjack analogy, you always split aces and eights. Occasionally, the dealer will still win, but it's always the right decision, statistically speaking. So if the dealer gets lucky and wins anyway, it was still the right decision.
7. How do you know when something (or someone) is aligned with you?
It's something that emerges over time. If I have the luxury, I prefer to just start working with someone on something to get a feel for what it's like to work with them on something meaningful. You don't always have that luxury—if you're thinking about switching a job, it's kind of hard to just start working with a competitor. But for both my startups, I worked a good amount of time on nights and weekends with my future founder before committing to anything formal, and a number of my consulting projects emerged from shorter conversations I had with larger corporates about their innovation platforms who decided that they wanted me to dive deeper. In one case, things felt pretty good, and we got pretty close to having me come over and stand up a corporate venture fund for them… until the project champion got lured away to a different company.
8. What’s one unconventional habit that keeps you sane?
I have three teenage girls, so I spend a lot of time hiding in the bathroom.
9. What do people misunderstand most about you?
That I'm often kidding and joking at the same time. I might take an extreme position and wrap it in humor to make it more palatable, but there's often a core bit of critical feedback there. Because I'm smiling when I say it, some founders think I'm joking and miss the main point.
10. If you could leave only one sentence behind, what would it be?
Eat what's put in front of you. Someone else did the work so you don't have to. Don't complain and don't redo it. Just take the win and move on to other things that need to get done.