I Trusted the Wrong People at MapQuest

At MapQuest, I had no community. To be fair, it was Lancaster, Pennsylvania in the 90s. Who knew what a startup community was? I had colleagues. I had a company. I had leaders who smiled in support at executive meetings but had their own agenda in the hallway.

I trusted them anyway. I thought they'd understand what I needed, look out for me the way you'd hope a mentor would.

I got burned. More than once.

A few years ago, we had a MapQuest 25-year reunion and a colleague who joined after I left said to me, “I have been involved in many aspects of growing this company in the formative years, and when I dug into the history, I could not believe how many critical projects that had your name on them.”

That's the whole difference between real influence and assigned leadership power. I had an influential role, not a power role. Influence comes from something nobody can hand you — not a board, not a boss, not an org chart. I was influential because I always put the company, the project, and the idea first, not myself. The people who mattered most trusted me.

Trust takes time. You can't shortcut it, no matter how badly you want to. It builds one honest conversation, one kept promise, one showed-up-when-it-mattered moment at a time.

First, trust has to be earned. Nobody owes it to you because you had a good idea, raised a round, or got promoted. You earn it the same way every time — by seeing what needs to be done and then by doing what you said you'd do, especially when it's inconvenient.

Second, trust must be seen. It's not enough to be trustworthy in private. People need to watch you make the hard call, keep the confidence, show up for someone with nothing to gain. Trust nobody witnesses doesn't spread.

And third, trust cannot be assigned. This is the one that took me the longest to learn. I've watched leaders try to install someone as the community's "connector" or "mentor," only to watch the community shrug and go find its own person anyway.

The deepest trust comes from something else: having actually lived the journey, and being willing to talk about it honestly. Not just the wins. The losses too.

I needed that at MapQuest. I needed someone who'd already been burned, who could say "yeah, that happened to me too" and mean it. Someone outside the org chart, with no agenda riding on my next move. A third party who had nothing to sell me and nothing to protect by managing what I heard.

I didn't have that person. So I spent the years since trying to be that person for somebody else.

That's what real influence looks like in a startup community. It's the founder who tells you about the round that fell apart, not just the one that closed. It's the mentor who admits they almost shut the company down in year two. It's the person willing to be seen struggling, not just seen succeeding.

Nobody assigns that person their standing. The community does. One founder at a time. One honest conversation at a time. One “how can I help” without creating a transactional understanding.

Assigned power runs the meeting. Real influence is who people actually call after the meeting's over.

That's the difference. And it's the only kind of leadership that actually holds a startup community together.