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Instead, I landed exactly one paying custo= mer, 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=E2=80=99t quit.= =C2=A0 Over the past 13 years, I=E2=80=99ve pivoted more times than I care to admi= t. From email prospecting services to launching a sales engagement tool tha= t 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=E2=80=99s about pivotin= g 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 ac= cepting 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 bett= er at dealing with it. ### Startups Have a Death Wish The California Honeydrops have a song called Live Learn that really resonat= es, "nobody could tell me, I had to find out for myself. I had to live, lea= rn, 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 be= neath the shiny veneer, is always messier, scarier, and more chaotic. Every startup, in my experience, harbors a hidden death wish. At Predictabl= e Revenue, it often felt like my business was actively trying to sabotage i= tself. In the earliest days, the "near-death" experiences weren't metaphori= cal - they happened multiple times a week. One lost client, one technical f= ailure, one employee crisis felt like enough to topple the whole delicate h= ouse 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 su= rging through my veins. But somehow, each time, we found a way to claw ours= elves back from the brink, even if it was just by our fingernails. With maturity and more battle scars, the frequency of these near-death expe= riences 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 de= veloped a thicker skin, better systems, and a network I could lean on. Ever= y near-death experience became less about panic and more about careful, mea= sured responses. Finally, after 13 long years on this rollercoaster, I've noticed the cadenc= e has settled - somewhat - to a rhythm of once or twice a year. Don't get m= e wrong: these semi-annual crises are still gut-churning, hair-raising even= ts that keep me awake at night. But now, they feel familiar rather than cat= astrophic. They're part of the landscape, an expected storm in the annual f= orecast rather than a once-in-a-lifetime hurricane. The lesson here isn't that your startup will stop facing crises - because i= t won't. The true lesson is that resilience builds quietly beneath the chao= s. 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 p= art about rollercoasters is that they have a tendency to go both down and u= p.=C2=A0 In other words, it's not the company=E2=80=99s death wish that diminishes o= ver time - it's your ability to survive and grow stronger that steadily inc= reases. ### The Latest Drop: Betting Everything on a Pivot Five months ago, I made a decision that threw me back onto the steepest, mo= st terrifying part of the rollercoaster. I shut down our biggest revenue dr= iver 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=E2=80=99s net inco= me fell to -20%, February=E2=80=99s was -15%, March followed with -11%, and= then April plunged to an alarming -30%. Ironically, letting people go ende= d up costing even more money - money we didn't have to spare. On an intellectual level, I genuinely believed in our new positioning - "re= venue coaching for founders by founders." It was logical, aligned with our = strengths, and felt right strategically. But emotionally, I was spinning. T= he worries grew louder each night, spiraling through scenarios that felt in= creasingly real: =E2=80=9CIf PR dies I won't be able to pay the mortgage, w= e'll have to sell the house and move in with my parents. My family will thi= nk I=E2=80=99m a loser, my kids will hate me for making them switch schools= .=E2=80=9D 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=E2=80=99d have been having nightly anxiety atta= cks, staring at the ceiling until 3:30am, heart racing as worst-case scenar= ios played on repeat in my mind. This time around, the challenges were the = same - my bank account draining, debts climbing, and revenues tumbling simu= ltaneously - but I handled it differently personally and professionally.=C2= =A0 **Personally**.=C2=A0 My first stop was that I stopped obsessively checking metrics. Constantly r= efreshing dashboards only amplified my anxiety without improving my decisio= ns. I restricted myself to only looking at the budget/forecast model if I w= as going to make a change. I also kept a journal by my bed. Rather than letting my worries spiral endl= essly 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 s= cenarios. But Home Collin? He learned how to compartmentalize, to stay pres= ent with my family - even when things at work were falling apart. I=E2=80=99m still not entirely sure how I pulled it off, but I credit a sim= ple trick I learned in therapy. Anytime the anxiety started creeping from W= ork Collin into Home Collin=E2=80=99s territory, I=E2=80=99d ask: =E2=80=9C= Is thinking about this right now going to change what I do?=E2=80=9D If the answer was yes, I gave myself permission to sit down with Work Colli= n for 10 minutes, think it through, write it down, and move on. If the answ= er was no, I=E2=80=99d 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 pl= an. A real, well-thought-out plan. One that had been pressure-tested with peopl= e smarter than me. That gave Home Collin permission to stop spiraling. When= the anxiety bubbled up, I could remind myself, =E2=80=9CWe=E2=80=99ve alre= ady covered this ground. We=E2=80=99ve chosen the path. Now we just need to= walk it.=E2=80=9D And that=E2=80=99s what kept me moving: a repeatable process that gave me s= omething 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 fe= els 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 resul= ts and let the rest wait. 3. Pull those levers as hard as you can. Once you=E2=80=99ve identified wha= t matters, go all-in. Pour your energy into the signal, not the noise. 4. Repeat. Step back, evaluate, adjust if needed, then recommit. Progress i= sn=E2=80=99t always flashy - but momentum is built through relentless consi= stency. The hardest part? Resisting the urge to thrash. When everything feels like it=E2=80=99s falling apart, the instinct is to d= o something - anything. Refresh dashboards. Rewrite strategy decks. Panic-G= oogle what to do when your burn rate triples. But most of that motion is ju= st 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 h= appen, 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=E2=80=99s tracking at +35%. Refe= rrals are flowing. The pivot=E2=80=99s working. For now. But I=E2=80=99m not naive - the rollercoaster doesn=E2=80=99t stop. It neve= r gets easier; you just get better at staying strapped in when it jerks lef= t unexpectedly at 2 AM. What actually changes after 13 years isn=E2=80=99t the chaos. It=E2=80=99s = you. You stop seeing every dip as a death sentence. You realize that the pa= nic passes, the bank account refills (eventually), and even six-figure mist= akes won=E2=80=99t kill you if you can outlast them. You learn that companies trying to kill themselves isn=E2=80=99t a bug - it= =E2=80=99s a feature. That gut-punch email? That surprise churn? That terri= fying financial spreadsheet? It=E2=80=99s just Tuesday now. Most importantly, you realize that being a cockroach isn=E2=80=99t about br= illiance, boldness, or even particularly good decision-making. It=E2=80=99s= about one thing: refusing to let go one day longer than the chaos lasts. ### Your Turn on the Rollercoaster If you=E2=80=99re somewhere in the middle of a drop right now, let me leave= you with this: * Checking the metrics every hour won=E2=80=99t change them. * Your 3 AM anxiety isn=E2=80=99t 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-d= eath pivots, here=E2=80=99s what I know for sure: The highs are worth the lows. The burns teach you more than the wins. And s= ometimes, the smartest thing you can do=E2=80=A6 is just not let go. Welcome to the cockroach club.=20 Collin=20 PS - Does this sound like your startup journey? Let me know, I=E2=80=99d lo= ve to hear from you. =E2=80=94=E2=80=94=E2=80=94 You are reading a plain text version of this post. For the best experience,= copy and paste this link in your browser to view the post online: https://foundersedition.co/p/13-years-on-the-rollercoaster --ccafeb5f1c53ad91cf0a70865cfbcf77a3fbd579eba412a8012c8e85e3e6 Content-Transfer-Encoding: quoted-printable Content-Type: text/html; charset=utf-8 Mime-Version: 1.0 13 years on the rollercoaster
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May 30,= 2025   |   Read Online

13 years on the rollercoaster

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Hello Andrew,

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

Somehow, I survived. Friends jokingly call me "th= e cockroach" - not because of my entrepreneurial brilliance, but becau= se I just don=E2=80=99t quit.=C2=A0

Over the past 13 years, I=E2=80=99ve pivoted more times than I= care to admit. From email prospecting services to launching a sales engage= ment tool that soared to seven figures only to crash back down with breatht= aking speed. At one point, right before the pandemic, I even debated shutti= ng the whole thing down.

Truthfully, survival ha= s less to do with genius strategy and more with the ability to hang around = long enough to get lucky. It=E2=80=99s about pivoting when you have to, dou= bling down when you can, and having the humility to admit you're usuall= y 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 l= ike you're failing. The advantage you gain as an elder cockroach is tha= t 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, l= earn, 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, on= ce 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 metaphori= cal - they happened multiple times a week. One lost client, one technical f= ailure, one employee crisis felt like enough to topple the whole delicate h= ouse of cards we'd constructed. Each Friday felt like a survival milest= one rather than an achievement.

As we grew, those existential crises didn't vanish - they simp= ly spaced out a bit. Instead of weekly panic, we graduated to monthly disas= ters. 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 fingerna= ils.

With maturity and = more battle scars, the frequency of these near-death experiences slowed eve= n further. We started encountering serious threats to our survival quarterl= y. These were big, complex challenges: strategic missteps, significant mark= et shifts, or unexpected competition. But by then, I'd developed a thic= ker skin, better systems, and a network I could lean on. Every near-death e= xperience became less about panic and more about careful, measured response= s.

Finally, after 13 lo= ng 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: the= se semi-annual crises are still gut-churning, hair-raising events that keep= me awake at night. But now, they feel familiar rather than catastrophic. T= hey'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 bu= ilds quietly beneath the chaos. You gradually learn that just because the r= ollercoaster 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 t= endency to go both down and up.=C2=A0

In other words, it's not the company=E2=80=99s death wis= h that diminishes over time - it's your ability to survive and grow str= onger that steadily increases.

The Latest Drop: Betting Everything on = a Pivot

Five months ag= o, 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 Predic= table 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=E2=80=99s net income fell to -20%, February=E2=80=99s = 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 positionin= g - "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 scena= rios that felt increasingly real: =E2=80=9CIf PR dies I won't be able t= o pay the mortgage, we'll have to sell the house and move in with my pa= rents. My family will think I=E2=80=99m a loser, my kids will hate me for m= aking them switch schools.=E2=80=9D

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=E2=80=99d have been having nightly anxiety attack= s, staring at the ceiling until 3:30am, heart racing as worst-case scenario= s played on repeat in my mind. This time around, the challenges were the sa= me - my bank account draining, debts climbing, and revenues tumbling simult= aneously - but I handled it differently personally and professionally.=C2= =A0

= Personally.=C2=A0<= /p>

My first stop was that I stopp= ed obsessively checking metrics. Constantly refreshing dashboards only ampl= ified my anxiety without improving my decisions. I restricted myself to onl= y looking at the budget/forecast model if I was going to make a change.

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

= I recognized that my morning exercis= e routine sets me up to have a good day, physically and mentally. So I star= ted getting up ever earlier to get in a workout and a few hours of work bef= ore the kiddos got up. Even cockroaches need cardio.

Professionally<= span style=3D"color:rgb(44, 62, 80);">.

Somehow, I managed to split myself into two versions: Wo= rk Collin and Home Collin. Work Collin was constantly on edge, juggling fir= es and worst-case scenarios. But Home Collin? He learned how to compartment= alize, to stay present with my family - even when things at work were falli= ng apart.

I=E2=80=99m s= till not entirely sure how I pulled it off, but I credit a simple trick I l= earned in therapy. Anytime the anxiety started creeping from Work Collin in= to Home Collin=E2=80=99s territory, I=E2=80=99d ask: =E2=80=9CIs thinking a= bout this right now going to change what I do?=E2=80=9D

If the answer was yes, I gave myself permi= ssion to sit down with Work Collin for 10 minutes, think it through, write = it down, and move on. If the answer was no, I=E2=80=99d 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 co= uld remind myself, =E2=80=9CWe=E2=80=99ve already covered this ground. We= =E2=80=99ve chosen the path. Now we just need to walk it.=E2=80=9D

And that=E2=80=99s what kept me= moving: a repeatable process that gave me something solid to hold onto whe= n everything felt like it was crumbling.

<= h3 style=3D"color:#2A2A2A;font-weight:normal;mso-line-height-alt:125.0%;"><= span style=3D"color:rgb(67, 67, 67);">My Four-Step Survival Guide

Amid chaos, clarity came from s= implicity:

  1. Decid= e on a clear plan. Panic breeds confusion. A focused plan provides directio= n - something to anchor to when emotions run high and everything feels urge= nt.

  1. Identify the levers that move that plan forward. Not all work is create= d equal. Most of it is noise. Find the few actions that actually drive resu= lts and let the rest wait.

  1. Pull those levers as hard as you can. Once you= =E2=80=99ve identified what matters, go all-in. Pour your energy into the s= ignal, not the noise.

  • Repeat. Step back, evaluate, adjust if needed, then r= ecommit. Progress isn=E2=80=99t always flashy - but momentum is built throu= gh relentless consistency.

    • The hardest part? Resisting the urge to thrash.<= /p>

    When everything feels like it= =E2=80=99s falling apart, the instinct is to do something - anything. Refre= sh dashboards. Rewrite strategy decks. Panic-Google what to do when your bu= rn rate triples. But most of that motion is just noise masquerading as prod= uctivity.

    Much of the s= tress in entrepreneurship comes from feeling helpless. When I focused on do= ing excellent work and stopped obsessing over hourly metrics, the fog start= ed to lift. Clarity came not from knowing exactly what would happen, but fr= om 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=E2=80=99s tracking at +35%. Referrals are flowing. The pivot= =E2=80=99s working. For now.

    But I=E2=80=99m not naive - the rollercoaster doesn=E2=80=99t stop. I= t never gets easier; you just get better at staying strapped in when it jer= ks left unexpectedly at 2 AM.

    What actually changes after 13 years isn=E2=80=99t the chaos. It=E2= =80=99s you. You stop seeing every dip as a death sentence. You realize tha= t the panic passes, the bank account refills (eventually), and even six-fig= ure mistakes won=E2=80=99t kill you if you can outlast them.

    <= span style=3D"color:rgb(44, 62, 80);">You learn that companies trying to ki= ll themselves isn=E2=80=99t a bug - it=E2=80=99s a feature. That gut-punch = email? That surprise churn? That terrifying financial spreadsheet? It=E2=80= =99s just Tuesday now.

    = Most importantly, you realize that being a cockroach isn=E2=80=99t about br= illiance, boldness, or even particularly good decision-making. It=E2=80=99s= about one thing: refusing to let go one day longer than the chaos lasts.

    Y= our Turn on the Rollercoaster

    If you=E2=80=99re somewhere in the middle of a drop right now, let = me leave you with this:

    =
    • <= p style=3D"mso-line-height-alt:150.0%;padding:0px;text-align:left;word-brea= k:break-word;">Checking the metrics = every hour won=E2=80=99t change them.

    • Your 3 AM an= xiety isn=E2=80=99t 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 p= ivots, here=E2=80=99s 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=E2=80=A6 is ju= st not let go.

    Welcome = to the cockroach club.

    Collin

    PS - Does this= sound like your startup journey? Let me know, I=E2=80=99d love to hear fro= m you.

    <= span style=3D"padding-left:1px;">3D"=3D"in"
     
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