My framework for evaluating weird and wacky startups — Whenever you hear the story of a venture-backed unicorn, you’ll inevitably hear about the slew of VCs who had the chance to invest and didn’t, missing a huge opportunity. Perhaps the most painful example is AirBnB. Back when Brian Chesky was nobody, trying to sell 10% of the company for…

Featuring leaders at Amazon, Facebook, Microsoft, and Western Governors University — It takes guts for a man to genuinely speak up on behalf of women. It takes even more guts to spur action in an organization and lead a change for the better. Recently, I had the honor of moderating a Grace Hopper panel discussion featuring four men who’ve spent many…

Which numbers add up to “love”? — People talk about “customer love” a lot, but what does it actually mean? How do you know if you have it? Which numbers represent customer love? Over the course of my 16-year product leadership career, and in my role now as a VC evaluating startups, I’ve observed that you can…

Valuable takeaways from the front lines — Across 16 years, I’ve worked as a product leader at 5 companies in Silicon Valley (including eBay, Stella & Dot, and Betfair). In that time, I’ve seen true hyper-growth unfold: I was a director-level product leader at eBay when it scaled from $500M to $5B+ in 5 years, and I…

Recently, someone said to me, “You’re always smiling, full of energy, and ready to do your best — are you doing some kind of special meditation or regimen? What’s your secret?” She was convinced that I was following some extraordinary ritual. But even though I do meditate, that’s not the…

And do the work — “You have to believe in yourself beyond reason — otherwise, who else will?” My former boss, Jessica Herrin, Founder & CEO of Stella & Dot, used to say this onstage during keynotes. It was also, I think, her personal mantra. I always thought this quote was reserved for delusional founders…

As VCs stop funding money-losing businesses, healthy unit economics matter more than ever — After leaving my role as VP Product at Stella & Dot in 2013, I was excited to join a new mission-driven startup that was seeing explosive growth. …

Spero Ventures welcomes Sonny Mayugba as Entrepreneur-in-Residence (EIR) — “It’s not the strongest of the species that survives, nor the most intelligent, but the ones most responsive to change.” — Charles Darwin After evaluating the founder pitches for a recent accelerator class in late January, I packed up to leave when Sonny Mayugba, a founder with a huge smile…

Pitch and follow through (Part 4 of 4) — [This is part 4 in a series of 4. Before going any further, you may want to read Part 1: Do I really want to do this?, Part 2: Am I ready? And how much money should we raise?, and/or Part 3: Operationalize your process. …