Our 2023 Startup Story

In early 2023, a friend introduced me to the All-In Podcast, and it wasn’t long before I was hooked. This coincided with my experiments with new AI text-to-speech models. It led to a light-bulb moment: why not create a parody of All-In with AI-generated voices of its hosts — Jason Calacanis, Chamath Palihapitiya, David Sacks, and David Friedberg? The concept was simple yet intriguing — these popular hosts reimagined as AIs.

https://twitter.com/edwardbrawer/status/1632797438678368256

Our parody not only went viral, thanks to retweets from the hosts, but it also marked the inception of PodcastAI. The overwhelming response from listeners, filled with curiosity and praise, was a clear sign that we were onto something big. One such message came from Presh Dineshkumar, who I would later learn runs Founder University, along with Kelly Schricker. I could never have imagined that only nine months later, I would be pitching Roelof Botha.

My co-founder, Sean Duncombe, and I embarked on our startup journey back in late 2019. We learned not to fight network-effects, which is the startup version of fighting physics. We also learned that raising venture capital required being “venture qualified”, and having ground-game.

When ChatGPT came out in November of 2022, it was revolutionary. This was like 25–30 years ago when the modern web was being created. Sean and I were too young to participate by very little — and we were certainly in the wrong place as well. This time, it would be different. We knew we had to do something.

Around the time I was posting the All-In parody episodes, Presh had tweeted about Founder University’s 5th cohort, asking people to apply with their startup idea. I asked Presh whether I should apply, to which he responded “LET’S GO ”

I took that as a yes, and applied under the name PodcastAI. Sean and I purchased the domain name podcastai.com for $10,000, and we incorporated in April for $500 using Stripe Atlas, rather than spend a fortune using lawyers. Did I mention we learned a lot from our first startup?

We got into Founder University in May, and boarded a plane for San Francisco where Jason led the first session for 5th cohort of about 200 founders. I was part of few companies who pitched live to Jason that day. The moment he realized I was the “AI parody kid” was priceless. It was an amazing experience for Sean and me. We felt like we were finally in the game, or as Chamath would put it, in the arena.

A few months in, we had a meeting with Presh and Kelly, who offered us a $25,000 investment from LAUNCH, Jason’s fund (which runs both Founder University, and LAUNCH Accelerator, the accelerator arm — more on that later.)

We of course accepted the offer, which was the first validation of what we were doing. The $25,000 cheques served as a first bookmark for LAUNCH, who would re-invest in their winners. We built quickly, and ended up with our MVP live in late August and our first customers in September. It was that relentless product velocity that would have LAUNCH re-invest in us shortly thereafter.

In September, we were invited to a Dim Sum Dinner hosted by LAUNCH in NYC. We presented along with twenty other companies, many farther along than us, and got an amazing reception. Our presentation of PodcastAI, a SaaS platform that could automate podcast production, was a hit. We generated a lot of interest, and more importantly, Jacqui Deegan would soon invite us to the 30th cohort of the LAUNCH Accelerator.

We also got the opportunity to demo to Nick Calacanis, the producer of This Week in Startups (TWiST). We showed Nick how PodcastAI could turn TWiST into a fully automated website. Being in the arena meant having opportunity after opportunity. Powering TWiST certainly helped us to close 15 of 19 demo meetings on the spot between September and October. We stopped keeping track after that, but it was an amazing statistic for a nascent startup to have.

As you might have guessed, we accepted the invitation to the accelerator, along with its $100,000 follow-on investment. We returned to San Francisco for the kick-off, and met the amazing founders of the companies that would form our cohort: River (event coordination for influencer audiences), Melengo (full manufacturing for influencer clothing brands), Fanfare(Kickstarter on steroids), TaxGPT (the AI co-pilot for Tax pros), Tolt (easy SaaS referral programs), and Monic.ai (an AI study-aid for students).

Jacqui and Andre LeBlanc turned us into precision pitching machines. Every week, we pitched to a new panel of LAUNCH LPs, and honed our pitches to a crisp 3 minutes.

One of the greatest parts of being part of such a strong cohort is that we would all improve each other by example. We all quickly realized that the competitive pitch exercises Jacqui and Andre would run every week were really just dry-runs — yes, we were competing, but not really — we were all improving each other.

In December, Jacqui and Jason brought us all to Sequoia, where we had the opportunity to pitch Roelof Botha. For those who don’t know, Sequoia was the first venture cheque into Apple, and Roelof spearheaded Sequoia’s investment into YouTube. It was an unbelievable experience, one I recalled in the first episode of Imagine AI by Chris Madden. Towards the end I cover our vision of the future of podcasting, and how all the AGI talk resolves into a real product on our roadmap.

We were pumped. We had grown 56% in November, and wanted to keep our momentum going. Despite December being universally considered difficult for B2B sales, we did just that. Jacqui had turned us into pitching machines, but having an amazing product is what turned us into sales machines. We powered through the holidays and shipped features (Podcast rank tracking, and viral social post generation), all while closing sales and on-boarding customers. One customer, The Pitch, even invited us to be on their 11th Season, filmed in Miami. You can’t get more meta than that.

We got our last sale of the year late on December 31st, which took us to exactly 99.5% growth month-over-month. I’ve been rounding it to 100%, but that’s between us.

After our New Years party ended, I sent out our December 2023 investor update with our growth figures. It was still 11 PM in the bay area, and nobody would read it until the next day, but it was the last thing I had to do before calling it a year.