The best thing about entrepreneurship is you’ve got no boss. The worst thing about entrepreneurship is you’ve got no boss.

Boss is a terrible word. Mentor is a better word, but too vague to define a specific corporate reporting structure. What do people use? Manager? Not much better. Boss is a terrible word because the best of them don’t boss their employees around. That’s no way to bring out the best in us.

Manager isn’t much better because a great employee isn’t a burden to be managed. I’m just going to go with mentor. I’ve had some great mentors. They could have been bosses, but they chose to be mentors.

Nat Wasserstein was a great mentor. I worked for Nat early in my ETF career, when I was just getting started. He needed someone to figure out the ETF product development process as the product pipeline at the ETF startup XShares grew.

This was just before the Global Financial Crisis. Before most people knew what an ETF was. And XShares had just launched a massive suite of healthcare subsector ETFs, positioning them as verticals to access the coming biotech explosion that never came.

Nat is a deals guy. And an idea guy. And he put together some great deals, and had some great ideas. My job was to help with the execution.

The postscript to the XShares story is that the company didn’t really make it, but we did some great work nonetheless. We launched the first ever ETF white label platform, the first ever carbon credit ETF, the first ever mixed-asset ETF, the first target-date ETFs, and so on.

But I want to get back to mentorship. I want to get back to Nat.

So one day I get back from a meeting with the Chicago Climate Exchange. The CCX was our partner for a carbon credit fund that I was meant to build. They spent two hours of what was intended to be a half hour meeting explaining to me the difference between the different cap-and-trade markets, liquidity, and so on. And my head was spinning, I was lost.

I had a mess of a spreadsheet that I laughably called a project plan. Legal, compliance, operations, market makers, exchanges, marketing… a mess of tasks and dependencies and timeframes. I was unprepared and overwhelmed.

Nat looks at me with neither anger nor frustration and says “just get yourself organized and be here early tomorrow, I have something that will help you”

And when I came in the following day Nat was already there, and he hands me a book called “Theory of Constraints” by Eliyahu Goldratt, then sends me right back home to read it.

I have never seen that book used in the context of a financial services company before or since, and it was exactly what I needed. I would eventually become a decent financial product developer and product manager using the exact principles and processes described in that book.

What Nat knew is that I didn’t need a lecture, I didn’t need disapproval. I was already my own harshest critic. I needed a roadmap. And I needed just enough leeway to figure it out. And he was willing to accept the risk of me failing while allowing me to learn on the job. He had faith that I would figure it out. Without that leeway and without that faith my entire career that came afterwards would never have been.

It’s funny how small interactions during formative work years can stick with you for your whole life. The quality of character of the people you work for set an aspirational vision for what you can become and how to handle yourself within your profession. Nat wasn’t the only great leader at XShares. For a small shop there were at least a half dozen ETF careers that grew as a result of the work we did, and many still hold leadership positions in the ETF space today. I’d eventually move on to Rydex Investments where I got to work with several mentors, including Kevin McGovern, Tim Meyer, Kevin Farragher and others there who I looked up to and learned from.

All of this is on my mind. My kids were asking about my career path, and I couldn’t tell the story without telling them about my mentors. Parenting is a lot like mentoring in some aspects. The best bit of parenting advice I ever got was that if you see your kids in their best light they will live up to that image. I’ve always tried to do that. And I feel like the best mentors see their employees in their best light too. Not just for who they are, but for who they can become.

I don’t have any mentors right now, and I’m nobody’s mentor. I have partners now. Good ones. Justin Goldberg and Hunter Hopcroft are brilliant, hard working, positive people. Ethical guys. Smart guys. Real estate guys. With complementary skill sets. Startups are a battle, and I wouldn’t want to go into battle with anyone else.

Here is a story about my greatest mentor, and the day I became a great public speaker.

I was working at the New York Stock Exchange, and we’d invite ETF issuers to bell ringing ceremonies at the exchange. As part of the event we would give a short presentation on how the trading of their funds worked. And my job required me to stand up in front of the group of guests on the floor of the exchange and give that presentation.

When I say I was bad at it, that is not a humblebrag or an exaggeration. I was bad. I was terrible. And it wasn’t only that, I was nervous. The night before these events I’d already start to feel the panic. I dreaded it.

Most people would have been replaced from that task after their first mumbling presentation. And that was what I wanted. Put me out of my misery!

But that’s not what happened. That’s not what happened because instead of a boss I had a mentor. That’s not what happened because I was working with Laura Morrison.

I scheduled a meeting with Laura and proceeded to give her a dozen reasons why either the visiting company themselves, or anyone else at the exchange should give that presentation for all bell ringing ceremonies going forward. But she wasn’t buying it.

She just said “I think you should continue to give the presentation, and I think you are going to be great at it.” And then went on with her day.

I can’t say that I walked out of her office with immediate confidence. If anything, I was annoyed that she didn’t seem to hear me and let me off the hook. But wouldn’t you know it, the next time I gave that presentation it wasn’t that bad. And the next time it got a little better.

And to this day I seek out rather than avoid public speaking.

I’ll get back to X’s and O’s and REITs and markets on this substack soon. It’s been heads-down since the beginning of the summer as we’ve been working on IP to bridge the worlds of public and private real estate, and there are some big announcements coming on that front. But in the meantime I wanted to take a moment to reflect on some of the mentors who have been important to me and to express gratitude for the impact they have had.

This article was originally published in BakStack is republished here with permission