Ryan's Song

Ryan Breslow founded Bolt in 2014 as a first-of-its kind e-commerce solution enabling one-click checkouts. Breslow made headlines over the past week when news brokethat Bolt was attempting to raise a $450 million Series F round at a potential $14 billion valuation.

Breslow stepped down as CEO in 2022, but remains executive chairman of Bolt. According to TechCrunch, he misled investors and violated security laws by inflating metrics while fundraising the last time he ran the company. However, a letter to investors this week suggests a comeback as CEO following this proposed round – and a sizable $2m bonus to Breslow for returning to his former position.

I had never heard of Breslow before this week, but the deal terms are both audacious and suspicious. 

See: Eric Newcomer’s detailed analysis of the letter sent to investors and Peter Chun’s denouncement of his fund from the deal.

In 2021, he wrote a book titled “Fundraising”. I read it, so you don’t have to. 

10 key points from the book:

1. Fundraising is a ‘process’ which goes beyond checks & transaction. It’s important to seek and maintain deep relationships. 
2. Fundraising is a balance between skill and luck. “Have fun” in the process. 
3. Money is plentiful; you are the scarce resource.
4. Some founders are bad vibes; it is in your company’s best interest to avoid them. Great investors speak up when they disagree, but also respect founders.
5. Investors meet with 100s of founders but only back a few. Be unique. Investors are looking for visionaries, thinkers & warriors. 
6. Momentum is the most important part of fundraising (whether seed or Series F). Design a fundraising process around maximising momentum.
7. If raising for the first-time, follow 3 steps: a) Lay the soil: find a community of champions to be a part of through founder friends or mentors.b) Plant the seed: meeting investors before raising; you get to know if investors are a good fit for the moment you begin raising.c) Send it: generate some FOMO or play hard to get; perform due diligence by researching the investors’ thoroughly.
8. Earliest investors should get the lowest valuation caps. Those who back you early get the best terms. 
9. If investors add value to the business/company, try to keep them round for the company’s entirety if you can.
10. The best way to nail the pitch is to know your stuff. Either domain expertise or knowing users. Paint a picture of the market & where your product fits in. Demonstrate know-how and leverage.

As a first-time founder, I have my fair share of role models who have built valuable products and successful companies in the ‘right way’. Ever so often, I come across founders embodying traits to steer clear of. 

I read Breslow’s book to gain some perspective into his thought process. Overall, it's pretty alright (albeit generic) advice:

• I agree with the premise of being unique, perhaps less so about being a warrior.
• Knowing the product & market is key, and something I hope to nail down.
• Being careful when selecting investors is apparently quite underrated. I’ve come across many ‘VC horror stories’ online. 

Yet, I noticed an unnecessary emphasis on ‘relationship-building’ throughout the book. This is a seemingly critical part of the process, but the notion that “relationships trump metrics” is quite problematic, especially given claims that Breslow himself falsely reported metrics while fundraising. 

Viewing fundraising as ‘fun’ leads to playing mind-games with investors and ultimately focusing on the wrong things. At the end of the day, investors fund companies to generate ROIs. In my view, focusing on metrics is what I imagine would make the fundraising process easier, and ultimately more effective.

I don’t expect Bolt’s Series F to (actually) go through, but I doubt this is the last we will hear from the fun-raising founder.