I had a conversation with Jonathan about choosing what to work on, getting the government as a customer, fundraising and how too much money can hurt the culture, favorite interview questions and more.
Check out the full episode wherever you get your podcasts or right here on Substack. Sharing some of my highlights below.
How do you know you are working on a problem worth solving?
- You can feel if you’re solving a big enough problem for someone through their like reactions to things, such as people falling off chairs in conference rooms as we showed them what we could do.
What does product market fit feel like?
- Early government customers literally bought chain analysis on expense credit cards and used emails that didn’t have real government affiliation.
How do you sell to the government?
- The core strategy in selling to the government is: how do you make people’s careers?
How much of growth fundraising is about financial vs. the story?
People get behind the story and even very very smart people look at numbers differently depending on how emotionally bought in to the story they are.
Watch on YouTube:
Timestamps
00:00 - Introduction
04:11 - Growing up as an immigrant in London and the “chip on my shoulder”
09:18 - Why market sequencing is critical
16:23 - Choosing to take up the CEO role and the domain of sales
23:20 - Early transformational experiences and the entrepreneurial bug
26:13 - How to penetrate the government
30:57 - Importance of storytelling, emotional and intellectual storytelling
38:26 - Raising funds and why too much money can hurt a culture
42:23 - Lessons in creating a culture
48:50 - How to hire executives
55:44 - Jonathan’s favorite interview questions and hiring philosophy
1:02:09 - Exciting things in the next 20 years
1:06:44 - The “two-stage rocket” of fundraising
1:11:45 - Loneliness of being a CEO
1:12:55 - Rapid fire and closing questions
