Tyler Handley: The $65M Exit and Life After Inkbox

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Getting to the Deal

Exit Horizon

7 episodes

19 hours ago

Real conversations with Canadian business owners who've sold their companies, the advisors who guided them, and the buyers who made it happen. Host Krystyn Harrison breaks down what actually worked, what didn't, and what you can apply to your own exit - whether you're planning to sell in two years or just want to understand your options. From deal structure to life after the sale, we cover the practical and personal side of turning your business into life-changing wealth.

Entrepreneurship

Business

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Entrepreneurship

Business

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Tyler Handley: The $65M Exit and Life After Inkbox

Getting to the Deal

48 minutes 5 seconds

1 month ago

Tyler Handley: The $65M Exit and Life After Inkbox

In this episode of Getting to the Deal, host Krystyn Harrison sits down with Tyler Handley, co-founder of Inkbox, who transformed a jungle discovery into a $65 million acquisition by BIC in seven years. Tyler shares how a personal frustration with temporary tattoos led him to Panama's jungles, where tribes using fruit-based dyes inspired the breakthrough technology behind semi-permanent tattoos. He reveals the strategic pivot that made Inkbox irresistible to acquirers - repositioning from a tattoo marketplace to a replenishable beauty accessory - and discusses his unconventional negotiation tactics, including using an "alter ego" to overcome Canadian politeness during deal discussions. Beyond the mechanics, Tyler opens up about the mental challenges of exiting, from the eight-month process of stress leaving his body to untethering personal identity from business success, explaining why 75% of founders regret their sale within a year. If you're a founder building a consumer brand or planning your exit strategy, this conversation provides tactical insights on positioning for acquisition, negotiating from strength, and preparing mentally for life after the deal.

Show Notes:

00:00 The Birth of Inkbox: A Unique Tattoo Journey

03:01 From Idea to Market: The Kickstarter Launch

06:06 Scaling Challenges and the COVID Boost

08:59 Navigating the Exit: The Acquisition by Bic

11:59 Life After the Exit: Transitioning to a New Reality

15:00 Finding Purpose Beyond Business

18:02 Advice for Future Founders: Balancing Work and Life

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This episode is brought to you by Exit Horizon. Our mission is to help strategic Canadian founders build systematically toward fulfilling exits using proven methodology from entrepreneurs and advisors who've actually navigated successful deals. We compress the learning curve so you can build with the end in mind from day one, not piece together exit strategies when it's too late.

Apply now to join our next cohort or book a quick call to learn more about what might be the right place to start for your business. Visit exithorizon.com.