5000 hours with Jon Bradford: What I learned

March 2013, NYC:

I receive an offer to join the Techstars New York program to work as an Associate. The problem is that I'm still CEO of Frontlyst and in the process of winding down the company. An even greater problem is that I would have to get to NYC in 3 days.

A few weeks prior, my CTO Richard Lau and I had a heart-to-heart and we both agreed shutting down was the best thing to do for all. That's when, as a mad scramble, I hustled my way to a meeting with the Techstars NY MD and a job with the program.

I hastily send an email to Jon Bradford MD at Springboard, who I heard was merging with Techstars. I offer my help to the London program, where I could recruit new mentors or startups while I was in New York.

No response from Jon. What a dick, I think.

This is how I started my direct working relationship with Jon Bradford, formally from July 2013 to October 14, 2015. That's roughly 2 years and 4 months, or 5000 hours*. Not quite as much as Ben's time spent with Reid Hoffman, but enough time where I learned how he thinks.

I didn't go into the relationship blind. I talked extensively with Jess from the Springboard, people from his Difference Engine days, his F6S co-founder, and even the entrepreneurs he had funded. As much as he did his due diligence on me with David Cohen, Nicole Glaros, and Tom Chikoore, I did on him.

We did four Techstars programs together. I saw the cycles when he was first super engaged to when he was an advisor in the last cohort, and how he expertly switched questions and perspectives so that he would give maximum impact with minimal interaction. I saw the way he managed a family life while constantly hustling, and how he was successful but also struggled with balancing the two. I saw how he would let new mentors, Associates/Hackstars, and people slowly and carefully into his life.

Here are the five principles I've learned in my time spent with him:

  1. Batching:compacting work efforts so that you're doing only one thing in a short, defined amount of time, to maximize attention over a time span

    Jon is by far the best person I've ever seen that can ruthlessly batch and focus on one task, sprint to its completion, and then move on to the next task and do the same thing. He extended this thinking to the Techstars cohort as well - mentor week was super-intense, with mornings starting at 8:30 AM but we facilitated over 70 meetings in a few hours. Thursdays evenings were intense with 3 events including a social, but it was done to compact everything in one day.

    Through Jon, I've learned to batch my physical work space (for example Monday and Wednesday I work at Cyberport, Tuesday and Thursday Causeway Bay, and Friday I'm flexible) and how I utilize my work day (meetings generally in the morning, and work in the afternoon).

  2. Flipping:taking status quo power dynamics and flipping them around

    One demo day a year ago, we did something different - we were planning a few speaker events and panels in the morning before demo day. Originally we had thought that we would invite outside speakers for these events. This meant a ton more work as we had to identify which speakers we wanted, reach out to them, and then hoping most would convert.

    During one planning meeting, Jon surprised us and asked - "can't we just ask certain audience members to come speak, and instead of recruiting new people?".

    Immediately the dynamic turned. We knew we had found an elegant solution.

  3. Frictioning:finding, embracing, and surfacing points of tension

    Jon is ridiculously good at asking questions, in that those questions often compel the recipient to take a step back and pause before answering. Part of the secret is to find and anticipate questions that can cause friction, and to ask precisely those questions.

    He also has a talent in surfacing whatever's uncomfortable in a meeting - and making sure that's spoken about.

  4. Aligning:aligning life, family, and career, but also recognizing when life, family, and career is out of alignment

    Jon optimized his professional life by living in London during the weekdays, and then leaving for home for the weekends. One advantage of this was that he could 100% physically and mentally focus on work on the weekdays, but switch that focus on the weekends. Another advantage was that his home was remarkably close to the airport, which allowed him to be ultra-efficient when traveling.

    But from what I saw, Jon was able to understand when family, life, and career was out of sync - and he immediately addressed that gap.

  5. Short-Terming:extreme focus on only the things that are immediately actionable, and passing on almost everything else

    I don't think Jon ever thought of anything more than a month in advance. His ability and focus on the short-term allowed him to make great choices and have presence in the here and now.

    And if he didn't know something in the short-term, he would use the word "pass" to not deal with longer-term issues.

We started our relationship rockily. But after 5000 hours, I've realized that our now strengthened relationship is deeper than a mentor-mentee thing. I have seen some of his professional highs and lows. He's seen my professional investor start, my struggle with dealing with a new family member, and my thoughts and challenges in the next step of my career here in Asia.

I don't know what to call our relationship, but what I've realized is that I am and will continue to be grateful for his continued guidance and mentorship.

Happy birthday, JD.


  • I know the math is technically 4800 hours


  • I realized I didn't talk about how I became a better investor as well through Jon. But out of everything I learned it was his way of working with the program and with founders that impressed me the most.