Another Startup Raised on This Week in Startups

It’s been a long journey, but I thought I’d share how Jason and TWiST shaped my evolution from a rice-picking investment banker into a VC-funded startup founder / samurai.

But let’s start with today. I founded Beyond Pricing last June to provide automatic, data-driven dynamic pricing for the huge and fast-growing short-term rental and vacation rental market (think Airbnb, VRBO, etc.). We are now pricing almost $3M a month in bookings, doubling in size every 2 months, and have recently closed a nice seed round from institutional VCs and angels. But things weren’t always rosy. Through all the ups and downs, I’ve turned to Jason and his cadre of amazing guests to help guide me from taking the leap all the way through negotiating term sheets, pivoting, hiring, and every aspect of the startup journey.

Five years ago, I was getting antsy as a management consultant at Oliver Wyman. I was advising gigantic global airline and hotel executives on how to improve their revenue management and pricing. We created “Premium Economy” for some of the largest airlines in the world (you’re welcome). But I couldn’t stand working for someone else and just plugging away in spreadsheets and PowerPoint all day.

One of my friends had left Oliver Wyman to start his own company (which eventually became VideoPixie after going through YC), and it was my first friend to ever take the leap. I became intrigued and I wanted to learn more about startups. I was headed off on a road trip to the Sierras and for the drive, I downloaded TWiST. I think Jason was on Episode 5 with Dan Sacks. I was immediately hooked and downloaded the rest of the episodes back to #1 with Brian Alvey.

Every week, I religiously listened to the gospel of Jason. I absorbed everything.

About 6 months later, I quit my job and joined a fast-growing startup in Kenya. After a couple years abroad, I came back to the US. A recruiter quickly latched on to me and lined up two jobs at major billion-dollar established companies, one in Corporate Development and one as Director of Emerging Markets. Looking for the safety of a “respectable” job, I took the one in Corporate Development at a private-equity owned payment processor.

I lasted 5 months.

I’d been bitten by the startup bug and I couldn’t go back. I had developed that terrible trait that many founders or early startup employees have where they simply can’t go back – they are basically unemployable by a large company.

I quit and tried to work on my own company, which was creating a marketplace for booking experiences (skydiving, kayaking trips, etc). Problem was, I needed a technical co-founder.

Once again, I turned to the wisdom of Jason and learned about all the pitfalls of starting a company with someone you didn’t know. Instead, I simply taught myself to code. After a few weeks, I learned enough to be dangerous and built Wetter Feet myself. It was terribly designed, incredibly slow, and buggy. But it worked and I had a product, users, and even some revenue. This was a huge step for a former Ivy League investment banker who was used to being slotted into a well-oiled machine and just tasked with keeping the profit-making engine keep going.

I had taken the leap. I’d built something.

I bootstrapped the company, but it eventually failed. But I tried again. I met a fantastic co-founder who was passionate about Airbnb and the sharing economy and we built and we marketed and we hustled. We went through a pivot, a founder breakup, and a period of taking no pay to keep the company alive. And eventually, we raised a nice-sized round, partnered with some of the biggest names in the space, and started hiring and growing incredibly quickly.

And it has been a grind. But I didn’t come into it naively. Jason prepared me and taught me that it isn’t some glamorous, cool thing. It’s about persistence and hustle and more persistence.

I thought I’d share that journey for those folks that are part of the Jason-nation who have been sitting on sidelines waiting to jump in. I remember how inspired I was to hear about the success of early listener Don Charlton from The Resumator and that helped me keep pushing.

So keep grinding. Keep hustling. And thank you, Jason, for everything you do for this whole community. Whether or not you realize it, you’ve had a huge impact on a wide swath of would-be entrepreneurs.