The Craziest Startup Pivot He's Seen Actually Became A Unicorn

I have had the pleasure of knowing Eamonn Carey for many years. We first connected when we hosted him as a speaker at various events in Istanbul and Antalya. I always enjoy our conversations and learn so much from his experiences.

Eamonn began his career as a journalist before transitioning into the world of venture capital. His background in journalism provided great preparation for his work in VC. As a journalist, Eamonn honed critical skills like conducting thorough research, asking thoughtful questions, and listening closely to responses.

When Eamonn became an investor, he was able to effectively apply these journalistic skills to his new role. During investment meetings and due diligence, his training enabled him to gain deeper insights by probing founders with targeted questions. Overall, Eamonn's journalistic foundation gave him invaluable experience in research, interviewing, and listening intently. These capabilities directly translated into success when evaluating potential startup investments.

I found our conversation with Eamonn to be truly enlightening. There were many valuable insights that founders would benefit from listening to again and again.

"The dumbest, craziest, best thing I've done is start my first company." — Eamonn Carey

I took extensive notes during our discussion, especially around the lessons Eamonn has learned from investing in over thousand startups. A few key points really stood out:

• Successful founders do extensive preparation and discovery:

  • In-depth research on their market

  • Exhaustive customer discovery

  • Thorough investigation of competitors

  • Detailed data rooms demonstrating knowledge

• Best founders have an open, curious mindset:

  • Constantly seek feedback to improve

  • Intellectual curiosity to learn continuously

  • Driven to evolve from good to great

• Preparation is essential, as "Fortune favors the prepared mind"

• But top founders also have humility:

  • Admit gaps in knowledge

  • Boldly ask experts for help

• Stellar founders have true passion for solving problems:

  • Go incredibly deep on understanding their market

"Don't overthink things and don't be afraid to talk to other people." — Eamonn Carey

I asked Eamonn about the red flags he looks for during investor meetings with startups.

• Momentum and progress are essential red flags

  • Look for founders actively driving the business

  • Beware when founders are just waiting for investment

• Fundraising goals need clarity

  • Unclear or wide fundraising ranges are concerning

  • Founders should know how much they need and why

• Team dynamics require close scrutiny

  • Ensure all founders actively engage, not just one

  • Try to evaluate dynamics in person over a meal/coffee

  • Watch for co-founder relationship issues

• Other red flags:

  • CEO answering all technical questions

  • Lack of customer development, even at idea stage

  • Vague customer profiles and market understanding

• Body language and energy on calls provide clues

• Meeting founding team in-person invaluable to assess relationships

• Co-founder breakups before Series A common issue

I highly recommend this conversation with Eamonn for entrepreneurs to listen to or watch. 3 Books he recommends;

• Obviously Awesome by April Dunford - On positioning your business, not just marketing/branding

• The Hard Thing About Hard Things by Ben Horowitz - Discusses the difficult parts of being a founder

• The Mom Test by Rob Fitzpatrick - Guide on customer development for early stage startups

"The 3 most powerful words for a founder are 'I don't know.'" — Eamonn Carey