First job at age 10. Not glamorous. Cleaning dumpsters in a parking lot for $20 cash. Then a paper route for the Penny Saver. By 13, collecting carts at a grocery store. By 14, cashier. Labourer for a party supply delivery company 15-17. The early game was service industry, labour, and saying yes to whatever came next.
A summer internship at Cognos was the first taste of tech, writing wiki pages in HTML for Sales enablement that ended up helping IBM recognize revenue a quarter earlier than expected. The service work kept going in parallel: cashier manager at 17, then janitor and host at a restaurant, waiter and bartender by 18. At 20, assistant manager at Metro Grocery Department. By 21, two things running at once, a student intern at IBM Cognos in Business Analytics by day, still closing the grocery store at night. IBM did a round of layoffs at 22. A marketing role at Corel followed at 23, launching mobile apps on a small team.
Then things got interesting. Back at IBM as a UX Program Manager, building Design Thinking @ IBM and personally training over 7,000 people. Promoted to Portfolio Product Manager and Investment Program Lead, running a billion-dollar portfolio decision process alongside the GM of Business Analytics. The entrepreneurial itch had been there for a while though. Tattoo Hero launched out of Startup weekend in November 2011 while working at IBM. Then raised first money from Angels & FounderFuel, backed by Real Ventures, to build the vertical SaaS for tattoos. After that, a Director of Product Strategy role at Assent Compliance, building software to detect human trafficking in Fortune 500 supply chains.
The venture capital arc came next. VP of Product and Venture Partner at CoVenture, helping bring 20 companies to market. That led to Dignified, an agency and founder collective that shipped 30+ products for clients ranging from bootstrapped startups to Anheuser-Busch InBev (They make a lot of beer). Out of Dignified came Feathery, and then Codex, which pivoted to Squire AI, an AI code review platform. Y Combinator S21. The YC company ran for four years, many pivots, and was used by teams at Shopify, Coursera, Gusto, Cal.com, and many more.
After Squire, a year at Mintlify as Head of Customer Success then Head of Product. Now it's DevRel at Unblocked, plus a Venture Partner role at Pioneer Fund alongside 400+ YC alumni.
Off the clock: hiking, portaging, and camping through the backcountry, weightlifting and cardio for races, reading through a stack of books that never seems to shrink, playing playstation, or playing guitar badly but enthusiastically. Ikigai Isekai is what happens when a lifelong gamer decides to combine many hobbies into one project.