Navigating Entrepreneurship: Challenges and Strategies

Jeff Seibert is the Founder & CEO @ Digits, building the future of AI-powered accounting. Digits have raised funding from the likes of Peter Fenton @ Benchmark and 20VC. Jeff previously served as Twitter's Head of Consumer Product, a position he came to following the acquisition of his prior company, Crashlytics. Today, Crashlytics is the de-facto mobile crash reporting solution for iOS and Android and runs on over 6 Billion monthly active smartphones worldwide.

1. The Art of the Pivot:

• What are Jeff's biggest pieces of advice to founders pivoting?
• How do you know when you have enough data to make the decision to pivot?
• What are the single biggest mistakes founders make when pivoting?

2. AI: Who Wins and Who Loses:

• Why does Jeff believe that OpenAI will transition into an infrastructure play?
• What are the most significant challenges OpenAI will face moving forward?
• Why does Jeff believe that Apple are best positioned to win in an AI world?
• Why does Jeff believe that Google are the most vulnerable incumbent?
• What would Jeff do if he was CEO of Google?

3. LLMs: What Happens Now:

• Will we see the commoditization of LLMs?
• What are the biggest misconceptions people have on training and fine-tuning LLMs?
• Will we see LLMs increasingly specialise to vertical-specific models or will they remain horizontal?
• What is the difference between a thick and a thin wrapper when building on top of LLMs?

4. Angel Portfolio in Review:

• How many angel checks has Jeff written? How many failed? How many home runs?
• Does Jeff believe that company valuations are being kept artificially high?
• How did Jeff make 200x selling through the secondary market for a now failing company?
• What are Jeff's three biggest pieces of advice for angels today?