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Hey guys - we’ve spent a lot of time this week speaking with founders about how they made that (scary!) jump to going full-time on their start-up. 

The Story

Is it ever the right time?

The centrepiece for this article is Shensi Ding’s take on how she decided to go full time on her startup.

The Catch-22 is simple (not easy): you don’t have enough validation to quit your job and go full-time, but you won’t have enough validation until you quit your job and go full-time… so now what? 

When building a startup, timing your departure from your job is crucial.

Shensi was working as Chief of Staff at Expanse (now acquired by Palo Alto Networks), and Gil was Head of Engineering at Untapped, a recruiting tech company. 

While movies about Silicon Valley make it seem like all founders dramatically quit their jobs to go head-on into building the next “Google”, the reality is starkly different.

As mentioned by Reid Hoffman (co-founder of Linkedin) in his book Blitzscaling, most successful founders tend to be the best risk mitigators, not risk takers.

This means that most successful founders spend time making sure that their idea is the “right” one, before jumping head-on into building it. A few notable examples of this include: 

1. Steve Wozniak (co-founder of Apple), who continued to work at HP for almost 2 years (after the Apple II computer was launched) until he went full-time with Steve Jobs; 

2. Sara Blakely (founder of Spanx), who held onto her job as a fax machine saleswoman deep into Spanx’s journey; 

3. And Reid Hoffman himself, who continued working on Linkedin whilst being at Paypal 

Shensi notes that this fixation on being “sure” from her co-founder, Gil, was actually extremely helpful: 

If you know a future founder who is struggling to take the leap - forward this email to them!

How “The Wait” should be used: 

Shensi and Gil used this time to bulletproof their thesis on the problem they were looking to solve. Here’s what had to come together before going all in: 

1. Founder market fit: 

   • Shensi and Gil wanted to make sure that they covered a problem that at least one of them understood inside out

   • Since Gil was Head of Engineering at a recruiting tech company, they started validating a “recruiting API” 

   • This didn’t work out because they realized the market wasn’t big enough but the idea of a unified API sounded interesting 

   • They landed on a cross-category unified API, because companies needed an integration solution that works across the different types of tools their customers use

2. Problem statement validation: 

   • Shensi and Gil spent over a year validating the problem statement itself, this included many conversations with dozens of employees from different departments to confirm that the problem existed 

3. Ideation: 

   • They then came up with a skeleton idea of what is now Merge, but pitching the “idea” of a product isn’t the best way to collect data

   • Many customers came back to them and said they would hypothetically pay a certain amount if the product existed… 

   • They found that the only way to confirm if this would work was to get into it full-time 

So when DID they take that final step? 

If you’re wondering which stars finally aligned for Shensi and Gil to quit their jobs and take that leap of faith - so were we. When we asked her, here’s what she said: 

What this means for you

Though slightly anti-climatic and non-scientific, this proves what has rung true for many generations of entrepreneurs. The final step is indeed a leap of faith, and there is no perfect time or formula because if there was, everyone would follow it. 

All you can do is make sure you’ve done as much work as possible, here’s how: 

1. Founder-market fit, make sure you’re the right people to solve this problem (based on your work and life experiences) 

2. Problem statement validation, make sure the problem exists (sounds obvious, but is not…)

3. Idea validation, make sure people are genuinely enthusiastic about your solution to the problem (i.e., don’t give a drill to someone hanging up a painting because they’re both “tools”) 

4. Get going!

If you enjoyed this issue, please share it with fellow founders, operators, & investors and fill out our feedback form below:

See you next week!

Rahul & Aryaman