Someone asked me the other day how things are going at Bolster, the new company I started along with a bunch of long-time colleagues from Return Path last year. My visceral answer was “I’m having a blast!” I thought about it more after and came up with five reasons why.
First, I am working with a hand-picked group of people. My co-founders, I’ve worked with for an average of 15 years – we know and trust each other tremendously. And for the most part, the same is true about our cap table. Almost everyone else at the company is also someone multiple of us have known or worked with for years. That may not last forever, but it makes things so much easier and almost friction-free out of the gate here.
Second, this is the “second lap around the track” for a few of us on the founding team in terms of starting something from scratch, and even those at the company who haven’t done a raw startup before are super experienced professionals and many have worked in and around early stage businesses a lot. All this combines to cut down our error rate, reduce anxiety, and speed up the pace of work. More friction-free or at least low-friction work.
Third, after a 20-year run at Return Path, it’s great to start with a clean slate. No mountains of tech debt and legacy code bases. No installed base of customers with contracts or pricing we no longer like or offer. No institutional debt like a messy cap table, legacy people issues, leases for offices we don’t want or need any more. This also points to low friction as part of what’s going on…and while that’s a theme, the next two areas are different.
The fourth reason I’m having a blast at Bolster is that I love — and really live in — the problem space we are working in. When we started Return Path, I was deeply familiar with email marketing and the challenges faced by our client set and had a good vision for the early product. But as the years went on, the product got geekier and nicher — and even when it wasn’t, I was never a USER of the product since I’m not an email marketer. In fact, at our peak of 500 people, the company employed one email marketer and therefore had one user of our own product. At Bolster, we have three user personas — Member, Client, and Partner. And I’m all three of them. I’m constantly in the product, multiple times a day. I’m deeply familiar with all angles of the executive search and board building process. It’s MUCH better to be this close to the product, and the same is true for many of our team members.
Finally, the thing I was really worried about with starting another company from scratch — moving from a leadership role into an individual contributor role — has been nothing short of fantastic. I love working with clients. I love talking to members. I love advising and coaching CEOs. I love being a pretend product manager. I love writing marketing copy. It’s just great to be on the front lines. (I still love working on strategy and leading the board and engaging with people internally — but those are things that never stopped being part of my day to day.)
I was trying to think if there’s some priority to this list. Almost all of these items are or can be made to be true in your second+ startup. But while four of the five can theoretically be true in your first startup as well, I don’t think it’s quite the same. So I’d have to weight “second lap around the track” a bit higher and also note that during your second lap around the track, hand-picking your team and cap table, appreciating a clean slate, and appreciating individual contributor work are that much easier and things you can appreciate a lot more as a repeat entrepreneur.