Developer joins startup, becomes CTO, then buys it for $1

Executive overview

Don Pottinger joined Kevi as a junior developer in 2014, became CTO within six months, and eventually bought the entire company for one dollar when the investor was ready to shut it down. The company had gone through a full pivot, two rounds of layoffs, and a cap table so messy it blocked every funding round.

Owning the code, the customers, and the relationships made saying "I want to do this without you" the most de-risked bet available.

From developer to CTO in six months

• Joined Kevi in December 2014, attracted by the founder's track record (co-founder of Pardot, sold for ~$100M)
• Company was competing with Zapier in e-commerce data routing; churn was high
• Early 2015: pivot decision triggered departure of the most senior engineer
• Stepped up to lead a greenfield rebuild as director of engineering, then CTO a few months later
• Prior consulting background at Accenture gave him comfort with sales, customer conversations, and team leadership

The pivot and its cost

• Old product scrapped; new platform built from scratch for e-commerce email marketing (competing with Klaviyo, MailChimp)
• Two rounds of layoffs reduced the team from ~20–25 to a handful
• New CEO promoted internally — both she and Don were young, learning in real time
• Investor injected ~$300K to fund the rebuild: essentially a new company under the same name
• Rebuilt to $250K ARR (~$20K MRR) over 18 months

The cap table problem

• Original founders and early leavers held large equity stakes; Don and the CEO held ~5% each
• Investors in Atlanta saw the messy cap table and passed, regardless of product or revenue traction
• Lesson: early investors should take 10–20% per round; founders should retain 80–90% collectively in pre-seed/seed stages
• A small check (e.g. $25–50K) that takes 50–60% of the company kills all future fundraising options

Buying the company for $1

• CEO left in late 2016; investor was ready to shut down
• Don proposed buying the assets outright rather than finding a new CEO
• Conversation happened face-to-face, in real time — Don asked to continue "without you"
• Investor calculated the company was a minor line item for him but potentially life-changing for Don
• Don delivered a physical dollar in an envelope to complete the transaction
• Investor likely benefited from a tax write-off on prior losses, softening the cost of the $1 price

Running it solo

• Took over 100% ownership but had 0% of the team — fully solo from day one
• Handled sales, support, marketing, and all development simultaneously
• First six months: hit a wall; burnt out trying to grow while running everything alone
• Stepped back and reframed the goal: lifestyle business over growth-at-all-costs
• Revenue covered expenses; cloud provider credits kept costs low
• Podcasts (including Startups for the Rest of Us) served as surrogate mentorship during isolated solo-founder period

The exit in 2019

• Built "smart features" with a data scientist friend: AI-driven email subject line scoring and automated copy generation
• Wife's fourth pregnancy and desire to stop full-time work prompted Don to explore options
• Joined Google in April 2019 while simultaneously running Kevi and running a sale process via a broker
• Declined acquirers who required him to join post-acquisition
• Sold to a venture studio with a complementary SaaS product and in-house technical capability
• Signed the acquisition papers in the hospital the day his fourth child was born
• Exit: life-changing money, not "never work again" money; strong competition from Klaviyo made the timing right

Starting over: Lengua Talk

• Co-founder found on Indie Hackers — an experienced marketer who had already built in the language-learning space
• Launched January 2021; reached mid-six-figure ARR within ~8–9 months
• Second-time advantage: faster execution, better judgment on when to stop, knowing the marketing levers
• Pandemic timing helped: platform connects language learners with tutors over video
• Planning to expand from five languages to significantly more