These marketers quit their jobs to acquire an AI startup through Tiny Acquisitions

These marketers quit their jobs at an agency to acquire an AI startup through Tiny Acquisitions

These marketers quit their jobs to acquire an AI startup through Tiny Acquisitions

We all have friends or colleagues guilty of using a casual car selfie, expertly cropped group pic or picture of them on vacation as their professional profile picture (think: LinkedIn and Slack).   

More common than you'd think, right? Professional headshots are pricey, and let's face it, we all cling to that same old profile picture for years.

Enter Keegan and Rachelle; the two, now co-founders, who first saw Bettershot on Tiny Acquisitions. 

What started as a late-Sunday night scroll for Rachelle quickly turned into a life-changing decision. "I was dreading Monday morning, found Bettershot on TA, and thought, 'Why not?'. 

From Marketers to Startup Owners

Keegan and Rachelle's journey began at a B2B SaaS marketing agency, Rachelle, leading Strategy and Success, hired Keegan as the Director of Marketing.

 “I loved him [Keegan] right from the start. He had such an infectious personality and energy you just wanted to be around, even through Zoom… but I never thought we’d own a startup together!” Rachelle recalls.

After ten months, the duo was ready for something new. Keegan, with his background in performance marketing, working for companies like LinkedIn and 2U, had already been angel investing.

I've invested in several startups as an angel investor- Bedrock Ocean Exploration, Nautilus Labs, and Liveblocks to name a few. Working closely with these founders ignited a passion to be a founder myself, as I gained a ton of insight into what it takes and found it to be aligned with my own skill set” said Keegan.

They both saw that the demand for AI-generated photos was starting to grow. Competitors were seeing huge success — generating $84K in MRR in < 2 years. 

So, they invested $8,000 into Bettershot, an AI headshot tool with a solid MVP. 

Breaking even seemed straightforward – sell 276 units at $29 each. Simple, right? Not quite. 

"Running a startup is a different beast. We faced unexpected costs and our initial outputs were... let's just say, not worth $1M ARR," Keegan laughs.

(Left: early Bettershot outputs; Right: updated Bettershot outputs)

But fortune favors the brave. 

"Our stroke of luck? Maintaining strong ties with the original development team. We kept that going after acquiring Bettershot," the pair shares.

The Rollercoaster First 90 Days

The duo worked part-time on Bettershot while they wound down their jobs at the agency. They mapped out the necessary product enhancements, a go-to-market strategy, and potential partnership opportunities. Once they were ready to leave the 9-5, they had a game plan to take action on.

They met up in-person in Denver, Colorado for a week of planning their go-to-market, white boarding strategy, and recording content for their LinkedIn, TikTok, and Instagram feeds.

They began to reach out to professional and comedic influencers like Austin Nasso to create sponsored content. 

Their initial launch was November 22nd, generating first-week revenue of $2.6K+ through network tapping and a bit of influencer marketing.They’ve now generated over 40,000 headshots, and the images have evolved from quirky AI photos with lots of strange elements, to highly professional, consistent headshots.

Why Tiny Acquisitions Was a Game-Changer

"I checked out a bunch of other platforms. Tiny Acquisitions was by far the easiest to use and started communicating with sellers right away,”says Rachelle.

“I really liked the varied price point of tools on Tiny Acquisitions - it made the dream of buying and growing my own company much more realistic.”

"I thought you needed deep pockets or insider connections to buy a startup. But Tiny Acquisitions leveled the playing field. They made it possible for us to chase our dreams and work on something truly fulfilling. Tiny Acquisitions wasn't just a platform; it was our ticket to happiness and freedom in our professional lives.”

To get 120 headshots for just $29, go to:

Use code ‘TinyA’ to receive $4 off at checkout!