“Entrepreneurship is jumping off a cliff and building the airplane on the way down.”
You have heard it before, probably while half-awake in a lecture hall or doom-scrolling LinkedIn. The line is a cliché, yet the physics are painfully accurate. And yes, we know “pitching a tent” carries alternative connotations. Keep the smirk; the metaphor still fits. Founding a company is like throwing up canvas in a gale and hoping the poles stay upright long enough for you to catch a breath.
We are launching this Substack for three straightforward reasons.
Eat our own cooking. We tell clients to publish with purpose. If we leave our own story rotting in drafts, we are the shoeless cobbler.
Learn in public. Hitting publish forces clearer thinking than polishing private Google Docs that no one ever sees.
Escape the echo chamber. Feedback from strangers beats three polite Slack thumbs-ups from the same teammates.
That is the mission. Now, here is the Tuesday that convinced us it is non-negotiable.
The silent stall
For eighteen months Ozone Media Group ran like a perfectly greased conveyor belt: shoot, edit, deliver, repeat. Revenue climbed, but our field of vision shrank to the size of an inbox. We knew we needed to step back and work on the business instead of in it, yet every attempt felt like abandoning the controls at ten thousand feet. The result was a bright humming plateau; we were busy, but stuck.
Impostor thoughts crept in whenever the calendar showed white space. Were we still the right pilots? Was the brand genuinely growing, or only spinning faster? These questions simmered until one particular Tuesday moved them to the front burner.
Three jolts of clarity in a single day
Breakfast with brutal numbers
Nine o’clock, Nashville Entrepreneur Center. The founder mental-health roundtable opens with research that ricochets around the room before the coffee cools:
Founders are two times more likely to battle depression or suicidal thoughts.
Three times more likely to struggle with substance abuse.
Six times more likely to live with ADHD.
Ten times more likely to be diagnosed bipolar.
No one gasps; most simply nod. The turbulence has a name and a data set. The collective exhale feels like cabin-pressure equalization: we are not uniquely fragile, we are statistically normal for people who sign personal guarantees and then pretend to sleep at night.
Mid-morning validation and a mantra we needed
Same room, ten minutes later. Two battle-tested entrepreneurs, one shepherding a Tennessee whiskey label and the other shipping craft cocktail mixers by the pallet, swap war stories. Both compliment our model; one even recognizes the little ozone-swirl logo. Flattering, yes, but the real gift is the sentence they have earned the right to deliver:
“Ninety percent of entrepreneurship is getting your teeth kicked in; the other ten percent make it worth it, your tent-pole moments.”
The phrase lands harder than the praise. A tent-pole moment is the brief vertical spike that keeps the canvas from folding: a cold email that returns warm, a mentor’s two-word text that reads keep going, the impossible contract that actually gets signed. We had been searching for marble columns when what we really needed were poles we could hammer in, relocate, and hammer again as the wind shifted.
Payoff > Process
Six o’clock, Soho House Founders Club. The speaker tackles content marketing for people who would rather ship product than post selfies and opens with another sobering statistic:
“Ninety percent of podcasts quit before episode four, and of those that survive, ninety percent stop before episode twenty. Reach episode twenty-one and you have out-lasted ninety-nine percent of the field.”
Consistency, not cleverness, is the moat; keep shipping, aim precisely, and let data decide if you are improving.
During Q and A I’m volun-told to ask the first question because of my proximity to the microphone and say, “We often find ourselves getting all the way to the end of the sales cycle with a lead and they drop-off due to pricing, I need some guidance on how to communicate our value without going into the dirty work of all the hours that get put into our content creation.”
To which he replied,
“Stop selling the process; start selling the payoff.”
Prospects do not care which LUT we apply or what stabilizer sits on the rig. They care about the moment their marketing director forwards the finished reel with the subject line holy-wow-look-at-engagement. Sell that moment and the contract writes itself.
The tent-pole epiphany
Back at my apartment we unpack the day’s shocks, statistics, mantra, and payoff over some FIFA Ultimate Team.
Realization number one: we are not short on ideas; we are starving for tent-poles. Those spikes of proof are oxygen on the climb.
Realization number two: tent-poles, by definition, are lightweight and mobile. The whiskey founder hammers one whenever a new distributor signs. The mixer founder plants one each time a bar posts his product on social media. Our mistake was waiting for granite. Granite takes years; aluminum takes minutes and still holds the canvas.
We list every tent-pole since launch: first invoice, first referral, first DM from a stranger across the Atlantic, first client who paid early and called us partners rather than vendors. Forty-three poles in eighteen months; roughly one every two weeks. Each time, morale spikes, momentum follows, and the plateau tilts forward until the next lull. The pattern is obvious. No new poles, no propulsion.
The solution is mechanical: create more surface area for spikes. Publishing invites spikes. Honest outreach invites spikes. Asking blunt questions in public invites spikes. Every Substack issue, reel, or cold call is a swing of the mallet, another chance for the pole to bite.
Tent-poles serve three distinct jobs.
Record altitude. Plateaus feel flat because incremental elevation hides in plain sight. A scribble that says client used the word partner reminds you that you are higher than yesterday.
Recalibrate decisions. When you recall why the last pole mattered, your next strategic fork becomes clearer.
Refuel morale. Like a gulp of water halfway up Everest, the pole does not move the mountain; it moves you.
Each pole also delivers the speaker’s dictate in miniature: sell the payoff. A spike is, after all, a tiny payoff you can point to and say this is what we make possible.
The plan from here
Ship weekly, no excuses. Messy stories beat silent perfection.
Frame every narrative around outcomes, not overhead. Show the celebration, not the plumbing.
Measure relentlessly. Read-through rate, click depth, the DM that says “this landed” all count. Data vetoes superstition.
Reflect in public. If Tuesday’s post feels cringe by Friday, the cringe is valuable tuition.
Not every post will be a tent-pole moment. Without swings, however, there are no spikes, and spikes are the only antidote to the silent stall.
Join the climb
If you are fastening canvas to poles on your own windy cliff, or drafting that twentieth podcast episode because nineteen still sits in the danger zone, hit Subscribe. Expect field notes on content strategy, founder psychology, and the occasional unvarnished victory lap when a pole plants deep. Bring your stories as well. Reply, comment, or forward this to the builder friend who needs their next spike.
Gravity is not pausing, and neither should we. See you next Tuesday.
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Incredible. Keep it up!