Daniel Burka ran design at Digg in its peak years and co-founded two startups: Pownce, sold to Six Apart in 2008, and Milk, sold to Google in 2012. The Milk deal took him into Google Ventures, where he spent five years as a design partner and helped build the Design Sprint.

In 2018 he left all of that to work on hypertension. Simple, the open-source app he built at Resolve to Save Lives, now manages over six million patients in India, Bangladesh, Sri Lanka and Ethiopia. In 2025 he stepped down to go full time on Hard Problems, a nonprofit he co-founded to pull more designers toward that kind of work. We recorded this in London, about a year into that move.

00:24 "Entrepreneurship for me is…"
01:21 The mission of Hard Problems
02:33 Leaving Google Ventures: "I could do almost anything"
05:57 Money, privilege & the career-decision spreadsheet
10:36 What's stressful: keeping momentum at a nonprofit
12:30 Coping with stress & using pressure in a healthy way
16:39 Thinking in 10–20 year time horizons
20:48 Urgency vs. strategy: driving from ditch to ditch
24:09 What investors look for in founders
29:24 Staying a maker: ideal team size & how to fund it
36:45 Purpose, and how Daniel found his
43:36 Choosing co-founders & creative tension
48:33 Hopes, fears & knowing when to keep going
55:36 Why founders fail & turning doubt into action
01:04:36 What keeps Daniel up at night
01:10:24 Wrap-up

Jonathan Courtney is the co-founder of AJ&Smart, the Berlin agency that helped make the Design Sprint famous and trained thousands of facilitators through Workshopper and facilitator.com.

In September 2026, after 16 years, he handed the company to his team and announced he was leaving to become a musician. We recorded this three weeks into that decision.

Chapters
0:07 What entrepreneurship really means to Jonathan
2:14 Why money is just a scoreboard
4:33 Leaving his business after 16 years
7:03 Buying a piano and a 12-hour first session
12:23 The Saturday that changed everything
16:51 "Do it on the side": the comment that made him defiant
19:38 What kept him from creative work for 15 years
25:56 The doubts: money, status and identity
32:21 Why "stuck" people don't really want it
34:45 "Next year" means never: the power of urgency
39:32 Sharing unfinished work
43:39 Accepting that people will laugh at you
48:54 The "What You Already Know" workshop
56:14 Why he waits for permission
01:06:27 The promoter mindset: business lessons for musicians

Jonathan is still finalising the "What You Already Know" workshop. Sign up at alen.me and you'll get the questions as soon as they're ready.

Entrepreneurial success has less to do with strategy than we like to admit. Two founders can have the same idea, the same market and the same money, and one wins because of what is going on between their ears. Yet almost every podcast interviews founders about The How. This one interviews them about The Who.

Each episode a founder lies on the couch and we go into the mindset, the pressure, the stories they tell themselves and the ones they hide. Hosted by Alen Faljic, founder of d.MBA. Follow the show and catch episode one when it drops.