13 years on the rollercoaster

Hello Predictable Revenue community,

Thirteen years ago this week, I naively launched a CRM platform, convinced I was about to change the world. Instead, I landed exactly one paying customer, watched my savings evaporate, and learned that changing the world was a bit harder than expected.

Somehow, I survived. Friends jokingly call me "the cockroach" - not because of my entrepreneurial brilliance, but because I just don’t quit. 

Over the past 13 years, I’ve pivoted more times than I care to admit. From email prospecting services to launching a sales engagement tool that soared to seven figures only to crash back down with breathtaking speed. At one point, right before the pandemic, I even debated shutting the whole thing down.

Why did I keep going? Stubborn persistence. Or stupidity. Probably both.

Truthfully, survival has less to do with genius strategy and more with the ability to hang around long enough to get lucky. It’s about pivoting when you have to, doubling down when you can, and having the humility to admit you're usually just making educated guesses (if you're lucky).

This cockroach mentality isn't glamorous, but it's real. Surviving means accepting you'll frequently feel like you're failing. The advantage you gain as an elder cockroach is that the chaos remains the same, you just get better at dealing with it.

Startups Have a Death Wish

The California Honeydrops have a song called Live Learn that really resonates, "nobody could tell me, I had to find out for myself. I had to live, learn, get burned, do it again."

Sure, from the outside, some startups seem to effortlessly go from 0 to 1. Headlines trumpet overnight successes, and glowing interviews tell stories of flawless execution and visionary genius. But the truth, once you peer beneath the shiny veneer, is always messier, scarier, and more chaotic.

Every startup, in my experience, harbors a hidden death wish. At Predictable Revenue, it often felt like my business was actively trying to sabotage itself. In the earliest days, the "near-death" experiences weren't metaphorical - they happened multiple times a week. One lost client, one technical failure, one employee crisis felt like enough to topple the whole delicate house of cards we'd constructed. Each Friday felt like a survival milestone rather than an achievement.

As we grew, those existential crises didn't vanish - they simply spaced out a bit. Instead of weekly panic, we graduated to monthly disasters. A lost account or a cash flow crunch once every few weeks still sent adrenaline surging through my veins. But somehow, each time, we found a way to claw ourselves back from the brink, even if it was just by our fingernails.

With maturity and more battle scars, the frequency of these near-death experiences slowed even further. We started encountering serious threats to our survival quarterly. These were big, complex challenges: strategic missteps, significant market shifts, or unexpected competition. But by then, I'd developed a thicker skin, better systems, and a network I could lean on. Every near-death experience became less about panic and more about careful, measured responses.

Finally, after 13 long years on this rollercoaster, I've noticed the cadence has settled - somewhat - to a rhythm of once or twice a year. Don't get me wrong: these semi-annual crises are still gut-churning, hair-raising events that keep me awake at night. But now, they feel familiar rather than catastrophic. They're part of the landscape, an expected storm in the annual forecast rather than a once-in-a-lifetime hurricane.

The lesson here isn't that your startup will stop facing crises - because it won't. The true lesson is that resilience builds quietly beneath the chaos. You gradually learn that just because the rollercoaster is pointing down right now, does not mean it will continue on this path forever. The best part about rollercoasters is that they have a tendency to go both down and up. 

In other words, it's not the company’s death wish that diminishes over time - it's your ability to survive and grow stronger that steadily increases.

The Latest Drop: Betting Everything on a Pivot

Five months ago, I made a decision that threw me back onto the steepest, most terrifying part of the rollercoaster. I shut down our biggest revenue driver at Predictable Revenue - our outsourced sales development service.

This wasn't an easy choice. It cost people their jobs, cost us six figures in severances and immediately erased a substantial portion of our revenue. Our financial statements highlighted the impact: January’s net income fell to -20%, February’s was -15%, March followed with -11%, and then April plunged to an alarming -30%. Ironically, letting people go ended up costing even more money - money we didn't have to spare.

On an intellectual level, I genuinely believed in our new positioning - "revenue coaching for founders by founders." It was logical, aligned with our strengths, and felt right strategically. But emotionally, I was spinning. The worries grew louder each night, spiraling through scenarios that felt increasingly real: “If PR dies I won't be able to pay the mortgage, we'll have to sell the house and move in with my parents. My family will think I’m a loser, my kids will hate me for making them switch schools.”

It's no wonder sleep became elusive. Each night felt like a staring contest with anxiety, waiting to see who blinked first.

What was different this time

If this was 10 years ago, I’d have been having nightly anxiety attacks, staring at the ceiling until 3:30am, heart racing as worst-case scenarios played on repeat in my mind. This time around, the challenges were the same - my bank account draining, debts climbing, and revenues tumbling simultaneously - but I handled it differently personally and professionally. 

Personally. 

My first stop was that I stopped obsessively checking metrics. Constantly refreshing dashboards only amplified my anxiety without improving my decisions. I restricted myself to only looking at the budget/forecast model if I was going to make a change.

I also kept a journal by my bed. Rather than letting my worries spiral endlessly in my head, I wrote them down each night. Turning abstract anxieties into tangible notes allowed me to acknowledge my fears without letting them consume me.

I recognized that my morning exercise routine sets me up to have a good day, physically and mentally. So I started getting up ever earlier to get in a workout and a few hours of work before the kiddos got up. Even cockroaches need cardio.

Professionally.

Somehow, I managed to split myself into two versions: Work Collin and Home Collin. Work Collin was constantly on edge, juggling fires and worst-case scenarios. But Home Collin? He learned how to compartmentalize, to stay present with my family - even when things at work were falling apart.

I’m still not entirely sure how I pulled it off, but I credit a simple trick I learned in therapy. Anytime the anxiety started creeping from Work Collin into Home Collin’s territory, I’d ask: “Is thinking about this right now going to change what I do?”

If the answer was yes, I gave myself permission to sit down with Work Collin for 10 minutes, think it through, write it down, and move on. If the answer was no, I’d remind myself that Work Collin had it covered - and that he could take the wheel again in the morning.

But here's the thing that really made that separation possible: we had a plan.

A real, well-thought-out plan. One that had been pressure-tested with people smarter than me. That gave Home Collin permission to stop spiraling. When the anxiety bubbled up, I could remind myself, “We’ve already covered this ground. We’ve chosen the path. Now we just need to walk it.”

And that’s what kept me moving: a repeatable process that gave me something solid to hold onto when everything felt like it was crumbling.

My Four-Step Survival Guide

Amid chaos, clarity came from simplicity:

1. Decide on a clear plan. Panic breeds confusion. A focused plan provides direction - something to anchor to when emotions run high and everything feels urgent.

2. Identify the levers that move that plan forward. Not all work is created equal. Most of it is noise. Find the few actions that actually drive results and let the rest wait.

3. Pull those levers as hard as you can. Once you’ve identified what matters, go all-in. Pour your energy into the signal, not the noise.

4. Repeat. Step back, evaluate, adjust if needed, then recommit. Progress isn’t always flashy - but momentum is built through relentless consistency.

The hardest part? Resisting the urge to thrash.

When everything feels like it’s falling apart, the instinct is to do something - anything. Refresh dashboards. Rewrite strategy decks. Panic-Google what to do when your burn rate triples. But most of that motion is just noise masquerading as productivity.

Much of the stress in entrepreneurship comes from feeling helpless. When I focused on doing excellent work and stopped obsessing over hourly metrics, the fog started to lift. Clarity came not from knowing exactly what would happen, but from knowing exactly where to put my energy.

And that made all the difference.

The View from Year 13

As I write this, May hit +20% profit. June’s tracking at +35%. Referrals are flowing. The pivot’s working. For now.

But I’m not naive - the rollercoaster doesn’t stop. It never gets easier; you just get better at staying strapped in when it jerks left unexpectedly at 2 AM.

What actually changes after 13 years isn’t the chaos. It’s you. You stop seeing every dip as a death sentence. You realize that the panic passes, the bank account refills (eventually), and even six-figure mistakes won’t kill you if you can outlast them.

You learn that companies trying to kill themselves isn’t a bug - it’s a feature. That gut-punch email? That surprise churn? That terrifying financial spreadsheet? It’s just Tuesday now.

Most importantly, you realize that being a cockroach isn’t about brilliance, boldness, or even particularly good decision-making. It’s about one thing: refusing to let go one day longer than the chaos lasts.

Your Turn on the Rollercoaster

If you’re somewhere in the middle of a drop right now, let me leave you with this:

• Checking the metrics every hour won’t change them.

• Your 3 AM anxiety isn’t helping - but focused action will.

• Every founder has imagined moving back in with their parents.

• You can be terrified now and still show up brave tomorrow.

After 13 years of wild swings, burned plans, rebuilt strategies, and near-death pivots, here’s what I know for sure:

The highs are worth the lows. The burns teach you more than the wins. And sometimes, the smartest thing you can do… is just not let go.

Welcome to the cockroach club.

Collin

PS - Does this sound like your startup journey? Let me know, I’d love to hear from you.