Was Mortgaging My Life Worth it?

At what point do we find out if all of our startup sacrifice was worth it?

The prevailing theory is that as Founders, we can justify our sacrifices of time, money, and emotional energy for the bounty of riches we'll enjoy on the other side. It's almost hard-coded into all of us the moment we take the plunge to start something.

But what happens when we're on the other side and we're forced to come to terms with whether or not those sacrifices were justified? Can we truly replace what was lost in getting here with what was gained through our efforts? What if we straight up made a bad bet?

Let me tell you a personal story about my journey as a Founder over 30 (very long) years of building startups and my assessment of a mountain of sacrifice on the other end.

The Sacrifice

What scares me about what I'm about to tell you is that it may come across like a "brag" about how much I sacrificed or worked. I can't imagine any other context where someone punishing themselves is considered a brag, but I've seen these stories get perverted to those ends. Let me be crystal clear: this isn't a brag — it's a warning.

I started my first company at 19 (30+ years ago) with less than $20 in my pocket and no idea what a business even was. I was as alone and helpless as you could possibly get, so to make up for my lack of knowledge, I just worked more. When I say "worked more," I mean every waking hour, 7 days per week, without holidays or breaks, for, oh, about 7 years straight.

I gave up friends, and relationships, and rarely ever saw my family for most of that entire time. I would continue at that pace for another 10+ years until at the ripe age of 37, my heart stopped beating. Did I take that as a sign to slow down? No, I got married, had kids, and started this company (same year). I literally found more ways to sacrifice my time and energy while doubling down on some future payout that was utterly undefined.

The Judgment

When we make these sacrifices, we create an unspoken pact with ourselves that says it's OK to do things to ourselves that any sane person would run from because it will all pay off. But when exactly do we cash those chips in? And what if it's not enough?

In my 40s, I moved my family to Beverly Hills, where my daughter was about to start school. This may surprise you, but real estate in 90210 is insanely expensive. If you ever want to feel like the poorest person who ever lived, hop on Zillow and go house shopping in that zip code. We did exactly that, and after a year of looking, we finally convinced ourselves we had found our dream home.

There was only one little problem — it had a nice little 8-figure price tag associated with it. Over dinner, my wife and I discussed this ridiculous purchase in what would be the unintended "judgment moment" of my career. Her opinion (she tends to be right) was, "This is a giant waste of money, and what we're paying for this would make sense in no other context."

My response was, "Look, I've worked 30 years to get to this point. I've sacrificed nonstop to make this decision at this time. It was all leading up to this moment. If we say no to this, every promise I made to myself to get here was a lie because I never really planned on cashing those chips in."

The Settlement

Now, I'm not defending my logic here; I'm just telling you how I felt. But my wife summed it up perfectly: "You did all of those things so that you COULD make this decision, not because you HAVE to." It stopped me in my tracks. A week later, we packed our shit and moved back to Ohio where we've been ever since.

I spent the balance of my professional career sacrificing for a "thing" that I thought I would want. Not necessarily a house, but some sort of material trophy that told me I had won something. I was 100% sure this was it, and it turns out — I was 100% wrong. The sacrifice was never about the "stuff," it was about freedom.

It's rare that we have a specific moment where we are forced to come to terms with the sacrifices we made in life, and, what's more, whether the bets we made were actually worth it. I've mortgaged a massive part of my existence for the one thing I never knew I was looking for — freedom. Was it worth it? Hell yes, and I'd do it again in a heartbeat.

In Case You Missed It

I Can't Have That — And That's OK (podcast) Starting a business involves a series of unique conditions, the three basic levels of ambition, and the uncertainty of the returns a Founder has to consider. So... what is the cost of ambition and how is it achieved?

How Much Should I Invest in My Startup? We often wonder whether every dollar of our personal savings should be going toward our startup, or toward our safety.

The Emotional Cost of Being a Founder When we talk about building startups, we talk about lots of costs: Staffing costs, the cost of capital, cost per acquisition, and cost of opportunity. But we never talk about the biggest cost – the emotional cost.