A new chapter: Sharing one of the most difficult decisions I have ever made

Five years ago I launched SurePath Capital Partners. I didn’t have a master plan. I just knew that I loved advising founders and loved doing deals. I also wanted to do my own thing. Early on, we made a decision to specialize in SMB software. I had been focused on the SMB software space since 2009 as CFO for companies like Shopify and Freshbooks and as a VC, investing in companies like Unbounce, SweetIQ, Localmind and many others.

That one decision was a big one. Before that, we were one of hundreds (thousands?) of advisory firms. All, presumably, populated with smart, driven, experienced professionals. All the same as each other. By going deeper in one area than any other firm could, we differentiated ourselves.

We had tremendous success in those five years at SurePath but I was always a reluctant banker. Investment bankers have a well-deserved bad reputation. They charge way too much for the value they provide. And most of the industry practices don’t translate well to the needs and context of tech startups. Nevertheless, startup life boils down to a few big moments where the right advice, contacts and deal-making experience can be game-changing. I knew there was a need. And, while the industry is challenging, I knew it would not be hard to offer better service and experience than most banks.

Switching gears for a moment, this past year has been one of tremendous change for me. My marriage ended. After dabbling around it for years, I went pretty deeply into Buddhism. That practice gave me the tools, patience, courage and compassion to not run away from the pain of change, but to go deeply into it. To fully experience what I was feeling, no matter how uncomfortable it felt. It also helped me learn everything I could from that loss.

A couple of insights came from this reflection:

Most of us don’t lead balance lives:

This is not an earth-shattering revelation, I know. Throughout my marriage, I often told myself that my wife and kids were my top priority. And I genuinely believed it. But looking back, that was not reflected in how I allocated my time and, more importantly, my presence and attention. Work expands to fill all available time. Left unchecked, it sucks everything you have. There is always one more email to send.

I know that my family got what little was left in the tank. I was not fully present. I was drained. I think that’s pretty common unfortunately.

I was clear on what I truly LOVE to do the most:

I have kept a journal for years. As I looked back on entries from the past few years, there was a clear pattern: the days where I came home most energized, fulfilled and excited were the days when I had a 1 on 1 coaching conversation with a CEO that moved the needle. I was no more excited closing a $10M deal vs. a $100M deal. It wasn’t about the money. What got me excited was the personal impact on the founders and execs of our clients.

Putting these two insights together, I knew that change was needed. Investment banking is an intense industry with no regard whatsoever for work-life balance. If I wanted to have a more balanced life and have more energy and presence to bring to people and priorities other than work, then I knew I needed to get out of this industry. Also, looking at what I love to do the most, if I had a do-over I would just coach and advise founders and companies.

COVID = Opportunity

COVID provided the do-over opportunity. In March we went from 8 active deals to 0. Capital markets dried up. I knew that if I was going to ever make the change that now was the time. Still, this was a difficult decision. One that would impact not just me, but my team members and our clients. We had millions in the bank. We could have just waited for markets to return. Working through it though, I knew in my heart that it was the right call.

We have wound down the investment banking business now. We have one final deal that we are working to close.

As for me, I have launched a new business focused only on what I love to do and get the most fulfillment from. I have coached CEOs and other execs a bunch over the years, but I am in the process of getting certified as a professional executive coach. I will be focused on CEO coaching, CFO training and some deal advisory work.

So, there you have it. Big changes. I have no regrets. Looking back on my past behaviour as a husband and father, I did the best I could at the time. Our experiences shape us. All of them. I would not be who am I today without them. And while we had massive unfinished business at SurePath, I would not have the clarity regarding the kind of work that truly drives me if I had not tried out banking.

Thank you for reading!