When you’re building an eighth startup, are there really any lessons left to be learned?

As it turns out, yes.

All those important lessons you learn over the course of a career can actually hurt you if you don’t know when to set them aside.

You have to see when it’s not a time to be the seasoned CEO and instead lean into your role as the scrappy founder — even if this isn’t your first (or your seventh) rodeo.

You can read the first seven lessons here:

A new venture and a new team

In 2013, I’d just started Trajectify, and I was looking for an interesting side-project to take on. Through a series of introductions, I met Martin Babinec.

Martin had founded TriNet, and he was working on creating an introductions app that helped build and strengthen relationships — a better LinkedIn, if you will.

I liked the idea, largely because I thought LinkedIn did a pretty poor job. I started working with Martin part-time, and we created IntroNet.

Martin funded us to hire a CTO (developer) and Product Manager. For the first six months, Nick, Tyler and I experimented, learned, and pivoted. We spent a healthy chunk of cash and gained a lot of information about our market. The idea was too small to be a company, so we needed to do more. If we wanted this business to succeed, I needed to be working on it full time.

I put together a plan and Martin funded it for $1 million, in tranches contingent upon meeting milestones. We expanded the team to nine and set out to build the product so we could start validating it in the market.

Instead of an MVP, we called our first version an MVE: our minimum viable experiment. There were questions to be answered. We felt that we needed to test several concepts, so our team negotiated the most important features and got to work. We planned to do our first release in three months — pretty aggressive when you’re starting from scratch with all new employees.

As we got close to that three month mark, it became clear that we weren’t going to make our deadline.

Our tech team was in over their head. The front end and back end teams weren’t well aligned. The product manager was drowning in project management.

What had gone wrong?

CEO or Founder?

Too late (and too much money spent), I realized my mistake. I was operating like the CEO of an established company, not like the visionary founder of a new startup.

I was out there pounding the pavement. I was trying to build the market for us, get investors ready for the next stage, line up partners who would test the product for us. All of that was important, of course.

The problem was that I hadn’t focused on what was happening inside the company. When I sat down with the team, I realized that we weren’t just missing our deadlines. We’d made compromises on the product and the features — ones that affected our product-market fit. We’d spent too much money on an unfinished product that wasn’t going to serve our intended market.

I’d been so busy looking at the company from the outside-in that I’d completely missed what was actually going on inside.

If you’re a regular reader, you know I’m a frequent advocate of the outside-in perspective. So why was it a problem here? Shouldn’t that view from a distance have allowed me to see and make decisions holistically?

If we’d been a more mature business, yes. If this team had years of systems, processes, and shared experiences behind them in our market, an outside-in perspective would’ve been perfect.

As it was, they needed a founder with his nose deep in the details.

The founder’s place is in the trenches

Looking back, some of my fondest memories are of visionary founders that made everyone around them crazy.

At one startup, I was the second hire — for a technology director position. We didn’t have a team yet, so I was building (hacking) a prototype the founders could show investors.

One evening I was in the office working on the demo, and one of the co-founders asked if he could watch me work, and stood over my shoulder. I tried to be polite and show him a few things I was doing. He continued to watch my computer screen. And the next thing I knew, he’d pushed my hand off the mouse and was doing dragging and dropping the widgets himself.

Of course, as an employee, I hated it.

As a founder? The truth is that sometimes it’s necessary to be obsessed with every single detail of your business. That might mean being a bit overbearing at times. It will probably mean that your team thinks you’re way too involved in the day-to-day operations of the business.

If you’d been operating for five years and had $1 million in revenue, I’d likely agree with them.

For early-stage companies, that visionary has to be invested in every decision that gets made. At IntroNet, I thought building a good team was enough. I thought that because I knew how to be a good leader, I could put together a group of people that would manage the day-to-day work without much interference.

I was wrong.

No young team is good enough to succeed without a hands-on leader right beside them.

(You can read even more about my experience at IntroNet here.)

Final thoughts

The founder and the CEO are actually two distinct roles. If successful, you will ultimately need both — the founder early, and, later, the CEO to operate and grow the business.

Hopefully all of us get to experience long, varied, and successful careers as entrepreneurs. We’ll get to be the wild-eyed visionaries and the grounded CEOs.

For those of us who are (and have been) so fortunate, the career trajectory might look like it starts at one end (wild-eyed visionary) and proceeds horizontally to the other (grounded CEO). But in truth, the path can be much less linear.

Some of the best founders are both visionary and detail oriented. We’ve discovered this through the tools we use in coaching and the Organizational Assessments we’ve done. The same is true for CEOs. This leads us to our belief that most successful founders have the capacity to be good CEOs. It is one of the pillars on which we’ve built Trajectify.

We may have to bring some of our early founder self and some of our seasoned CEO self to each step of the journey. At times, we may have to turn away from what we’ve learned and remember what it was like to be at the very beginning.

The key is knowing when to lean into each role.

We help leaders move from founder to CEO (and sometimes back to founder) everyday. Contact us to see how we can help your leadership and business grow.