The Distill - Luck, Timing, & Evolution

Greeting Pioneers,

I don't write intros. Jack writes intros. But this week Jack wrote two thousand words about learning to delegate, and this intro is apparently what he delegated. Lucky me. Here are 6 years & 6 months in 6 minutes (it's actually 5, but I love an alliteration).

-Rachel

Building in Public, Jack

Part One: The Backstory

The assignment here is simple: build in public. Share wins, losses, and anything useful I've learned over the past six months at PayFWDs.

But some background feels necessary. So here are six years, compressed into one cup of coffee.

In college, I tried every side hustle imaginable. Not because I dreamed of being an entrepreneur, but because I flat-out refused to wait tables, work a campus job, or cash a paycheck that sacrificed nights and weekends.

That allergy to normal kept bringing me to my sales professor's office: “How stupid is this idea? Is it scalable?“ “Should I incorporate?“ “Is it worth spending another grand to hit an MOQ and save a dollar a unit?“

Those questions, those conversations, and that constant pursuit led to an opportunity I'd categorize as incredibly lucky: building customer acquisition for a venture-backed startup as a junior in college. An intro from Professor X.

Not something most twenty-year-olds get to do. 100% luck. But that  luck doesn't exist without those questions, those conversations, and relentlessly chasing opportunities until one finally popped.

That opportunity became Honeysuckle Labs, a company I started in college. Back then, every startup had "Labs" in its name. Truth is, our first client had "Labs" in theirs, so we copied them like the dorks we were. They eventually dropped it. We never did.

Honeysuckle did one thing: customer acquisition for seed-stage ad tech startups with inconsistent pipeline. I focused on ad tech because my first client was in ad tech. We cracked outbound for them so we stayed in that lane, stuck to a niche, and lucky for us(again) the golden age of ad tech was taking hold. 

Eventually we grew to half a dozen clients and twice as many employees. I fell in love with growth. Growth hacking. Marketing motions. Building repeatable machines that created predictable revenue for startups.

But as we grew, I drifted further away from designing the systems. At 24, I went from scrappy growth hacker to running a team of college kids, and I was in over my head. No exit plan. No feel for the business side. Accounting, unit economics, none of it pulled at me. I just wanted to build, and the building kept shrinking.

To take the company to the next level, it needed me to become a manager. That version of jack wanted absolutely nothing to do with management. So I left to do it again. Honeysuckle would be fine, it did sunset shortly after, but only to become a newer, better version of itself that's still around today.

I joined another startup, got my hands dirty again, and had one of the best years of my career. And both fortunately and unfortunately… we got acquired. I'd been away from home for a long time, so I moved back to the river city, joined a large company, and tried to exhale.

After six straight years of startup life where sleep was for the weak, health insurance didn't exist, and compensation depended entirely on performance. I was ready for stability.

I bought a house. Married my best friend. Rescued a dog. And went through open enrollment.

All great additions. And still, there was a void - the specific emptiness that comes from an absence of impact. Corporate life left me unfulfilled. Eventually I resigned, took six months off, and tried to figure out what the next five years were supposed to look like.

Every road led back to the same place. Startup land. In October 2023, I joined PayFWDs to lead revenue generation. 

Part Two: The past 6 months / Growing Pains

When I joined PayFWDs, one pipeline existed: client referrals. My job was to build more. So I dusted off the old playbook and got to work. For a year and a half, I lived in growth. Building repeatable lead-generation systems. Building bridges from interest to opportunity to client. Building a CRM that could track, manage, and forecast. Building a sales philosophy centered around questions, driven towards emotions, and away from features. 

By the beginning of 2026, one pipeline had become five: client referrals, channel partners, outbound, inbound, and social. But I learned the hard way that a singular focus on growth is naive. We built demand faster than we built the systems that supported it. 

Pouring everything you have into one thing is the fastest way to move that thing forward. But left unchecked, barreling down the track with your foot on the floor, you can cause problems. “Good problems”, they say. But problems alas. Too many sales and a post-close system that barely existed. No clean way to take everything a new client handed us and transform it into what the implementation team needed to start onboarding. Onboarding the customers we closed became a bottleneck - or more appropriately, a chokehold.

The writing was on the wall, but I ignored it. FWIW, I'm not sure I'd have done it differently even if I had. Walking into a room and telling everyone to slow down because of a problem that doesn't exist yet is goofy. Some may find that irrational. I’d argue any mindset inside a startup that isnt “grow or die at all costs and don't take your foot off the pedal until growth threatens death” is orders of magnitude goofier. 

Adjust when it does - which is what I did. I checked growth and started building systems that scale with the growth, because any more acceleration would've cost us delays, broken promises, and a reputation that we couldn't out market.

But the biggest bottleneck wasn't implementation. It was me.

I'd spent my entire tenure at PayFWDs doing what I'd always done - designing, building, and executing everything myself. End to end. I knew it wasn't scalable. I also knew exactly what I needed to do next. Hire. Delegate. Manage.

And I kept putting it off because I was afraid. Afraid of boredom. The same fear that led to a departure from a company I built from the ground up, and ironically, the same fear that pushed me out of the corporate slog. Yes boredom, but more acutely put -  fulfillment. Doing the work is the fulfilling part. Touching the metal. That's where I'd always found happiness and excitement.

By December of 2025 it couldn't have been clearer - to take the next step, I had to hire, I had to delegate, I had to manage. So I did. I wasn't going to make the same mistake twice. I hired a marketing manager to run the systems I'd been hoarding. Together we hired a content creator and an SEO killer, plus an intern for the production work. That gave me back the one thing I'd been starving for, bandwidth, and I spent it building the next system that needed building - an internal one, built around automation, to give every future PayFWDs salesperson and project manager their time back. I hired an founder/engineer to integrate ai, reduce slog, & transform our company. I stood up an internal team across three departments so every opinion that mattered had a seat. I’m proud of what we built. What we’re building.

Somewhere along the way I realized that stepping away from the metal didn't mean I stopped building. Just that I had to evolve. Now I'm building the team. Building the machine that builds the next five pipelines.

And with AI disrupting everything it touches, we're already chasing entirely new growth engines I wouldn't have imagined touching just a year ago. And with it another hire. 

The last six months have been exhausting. We’re growing across the board. I was employee number fifteen. Today we're twenty-five. But we’re pushing through the pain, building toward the next painful thing.

My biggest takeaway from the past 6 months is that growing the thing requires stepping away from the parts of the job you thought you loved most. Pushing through fear and coming out the other side with a fresh perspective and maybe even a new found love. 

"I'm a great believer in luck, and I find the harder I work, the more I have of it." - somebody - probably a hard worker. 

jack

Come Meet & Catchup With The Louisville Startup Scene

Every month we find a couple more founders we didn’t know were here - who also didn’t know we were here, nor amplify, or vogt, or keyhorse.

Louisville is small but it’s also big and there’s a founder or a one-day founder working at a coffee shop in St Matthews who hasn’t found their tent yet.

Help us change that!

Amplify and KYX are hosting a “welcome to the ecosystem” night next month in partnership with all of the major organizations and accelerators in the area.

Each org will have a table/booth where you can drop by and get to know them + founders and founder-curious folks around to meet and build your community.

When: Thursday, July 23 at 5-7pm
Where: NULU Marketplace II (the expansion!)
Register: https://luma.com/gwqmrdho

If you have any ideas on how to make this event best serve our fellow founders, please let us know here: #event-communitynight

Founder, Operator, Automator - Whoever you are, whatever you’re building. Bring it out of your silo and into the arena. It can be a web page, an N8N workflow, paid ads strategy, or v1 of your app. Tell a room of fellow builders about it and let us give you some feedback.

5 mins to present.

5 mins of feedback.

When: This Wednesday at 5p.

Where: Cinderblock - 1205 E Washington

RSVP here: https://luma.com/ctsfdt1q

It’s also community day at the block, so join us for a day of work before tiny demo day.

See ya there

Fire & Ice Rescheduled

The guy in charge of fire and ice decided to schedule it on the same day his good friend is getting married. What an idiot. Said idiocy has led us to reschedule.

New date: Saturday July 11th

Time: 11a

Where: TBD - will have location determined by EOW.

RSVP here: https://luma.com/nyzi29xr

HackKentucky - Sept 11-12th

It’s back! Register for HackKentucky Sept 11-12th @ Mashup / Genuine. This will be a 1-day hackathon, starting at 4pm and ending next day at 8pm.

We’ll have speakers, prizes, food and amazing bounties. Register here: https://luma.com/hy24ycd1

Much more to come on this.

Note’s on The Distill’s co-EICs: Jack Crowdis & Rachel Edenfield

Jack runs the newsletter, helps run KYX. He’s a career startup kid, past founder, and current operator. Weekly contributor. Always editor.

Rachel’s the Founder/CEO of venture-backed Swell, and a driver of KYX. Routinely delivers the city’s sharpest long-form startup advice. Always re-edits Jack’s edits (including this bio).

Know someone who should read this? Forward it, or send them this link.

That’s a wrap 🎬
Keep showing up 👊 
Keep shipping 🚢 
Peace, Pioneers ✌️