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EO StudioWhy Entrepreneurs Must Trust Their IntuitionㅣRewind AI, Optimizely, Dan Siroker
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Raising a Series A in Public
Dan Siroker describes the unconventional decision to publish a seven-minute Series A pitch video, which drew two million views and led to NEA leading the round at a $350 million valuation.
- •The pitch was recorded in about three takes and posted unedited
- •Results: two million views, thousands of investment offers, hundreds of qualified meetings
- •NEA led the Series A at a $350 million valuation
- •Idea was not a consensus internally
Background, Rewind Overview, and Early Failed Startup
Dan introduces himself, Rewind, and its funding history, then recounts his first solo venture after Stanford. That year taught him the importance of distribution and how lonely working without a co-founder is.
- •Rewind is a personalized AI powered by everything you've seen, said, or heard
- •Sam Altman was the first investor and committed $1 million in the first meeting
- •Funding came from First Round, Andreessen Horowitz and NEA
- •His first solo startup taught him about distribution and loneliness
Lessons from Google and Joining the Obama Campaign
Dan explains why Google was a misguided way to learn entrepreneurship and how Barack Obama's visit to campus led him to volunteer and become Director of Analytics for the 2008 campaign.
- •Most of what he learned at Google was how to navigate Google
- •He thinks joining an early-stage startup would have taught him more
- •He flew to Chicago as a volunteer after Obama said "I want you to be involved"
- •The campaign's risk-reward mentality allowed analytics to play a new role
The A/B Test That Raised $40 Million
Dan recounts the campaign's A/B test of the homepage, in which an informal family photo beat the video the team expected to win. The lesson was the power of applying the scientific method to real-world decisions.
- •The team expected a compelling video to win
- •A black-and-white family photo dramatically overperformed
- •That one change led to an incremental $40 million in donations
- •A/B testing is the scientific method applied to the real world
Founding Optimizely: Making A/B Testing Easy
Dan explains how the campaign experience inspired Optimizely, a tool that let non-technical people run A/B tests without developers. He ties the idea to building the product you wish you had.
- •Existing tools were expensive and needed a developer
- •A JavaScript snippet and visual editor lowered friction
- •Optimizely skipped multivariate testing in favor of simple series of A/B tests
- •Your intuition is the product you wish you had
Optimizely's Growth Phases and Scaling Mistakes
Dan walks through Optimizely's rapid early growth and funding rounds, then the period of uncontrolled hiring. He explains how lack of discipline slowed the company and left him burnt out.
- •Reached about $7M ARR in three years and raised Series A, B and C
- •Raising more money than needed is fine, but spending it all is a mistake
- •He didn't say no enough to executives' hiring requests
- •Large team alignment slowed the company and squandered its lead
- •He fell out of love with the business after solving the original problem
Trusting Your Intuition and Staying Passionate
Dan says his biggest regrets came from going against his gut, and that a founder's intuition draws on many data points. He also reflects on delegating away the work he loved instead of modeling himself on a coding CEO.
- •He regrets times he deferred to a board member or executive against his gut
- •A founder absorbs many data points that form hard-to-articulate intuition
- •At Rewind he has more confidence in his conviction
- •Most decisions are two-way doors that can be reversed
- •Spending time on work that drains energy made him less effective
The Origin of Rewind and Scribe
Dan describes how losing his hearing and trying a hearing aid inspired the idea of using technology to overcome biological limits. Rewind began with a meeting bot called Scribe before pivoting.
- •A hearing aid revealed how much he hadn't realized he was missing
- •We all live like a horse with blinders on, limited by biology
- •It took 10 years to bring the vision to life
- •Scribe, a meeting-transcribing bot, was the first MVP
- •Users wanted more than meetings, and Apple silicon made the pivot to Rewind possible
Creating a New Category Instead of a Better Mousetrap
Dan explains why he prefers creating new categories to incremental improvement, using Rewind's passive capture as an alternative to note-taking. His advice is to focus on the problem rather than the technology.
- •Some people are wired for incremental optimization, but he prefers new categories
- •Note-taking requires foresight and effort, while Rewind is passive
- •Start from the problem, not a new technology like GPT-4
- •Signs of a new category include people gluing together existing products
- •Let the problem lead the technology
Building Trust Through Transparency
Dan explains the two pragmatic reasons for the public raise: building user trust around privacy and handling a flood of investor interest. He says transparency has paid off and sets a startup apart from big tech.
- •Rewind is a new category with privacy concerns, so trust is key
- •He wanted a video to send to the many investors reaching out
- •Runway went from three years to six
- •Growth is 15% month over month, mainly through word of mouth
- •Every bet on transparency has paid off so far
Build a Product People Want Before Flywheels
Dan advises early-stage CEOs not to obsess over flywheels and frameworks before making something people want. He uses Amazon as an example, saying it began with getting people books by mail.
- •Early on, the job is building a product people want
- •Flywheels and competitive advantage come later
- •Amazon's flywheel built on things that don't change, like selection, price and delivery
- •Amazon started with books by mail and selection unavailable elsewhere
- •He admits he has made the mistake of getting ahead of himself
Choosing a Problem Worth a Decade of Your Life
Dan gives advice on finding a problem to build a business around: be honest about whether it's a painkiller or a vitamin, and pick one you care about enough to live with for years. He says he would pursue perfect memory even if it failed.
- •Ask whether it is a painkiller or a vitamin
- •Change is hard, so the problem must be painful enough to change behavior
- •Be honest about whether you would change your own behavior
- •Choose a problem you could spend 10 to 20 years on
- •He'd rather fail at giving humans perfect memory than not try
AI, Purpose, and the Vision for Rewind
Dan closes by saying AI can't provide purpose but can serve it as a superpower. He hopes Rewind becomes as ubiquitous as glasses or hearing aids.
- •AI can't give humans purpose
- •AI in service of purpose is an accelerant, not a replacement
- •Tasks that don't serve purpose can be handed to AI
- •Rewind aims to be as ubiquitous as glasses or hearing aids
