Lindsay Kaplan co-founded Chief, built one of the most talked-about communities in tech, and then left to go on a year of soul-searching (and like many founders, angel investing). Coming out of that walkabout was Lindsay joining up with our friends at Bullish as a Venture Partner. In her new role, she’s hunting for “weird” consumer startups, founders rethinking categories, and companies building at the intersection of community, women’s health, and AI. Big thank you to Mike Duda, Bullish’s co-founder, for connecting us with Lindsay and helping us to make this interview happen!
TL;DR from our interview:
- She’s looking for consumer and consumer-adjacent companies disrupting new categories, with a particular interest in the loneliness epidemic, women’s health, and niche communities
- Her pitch meeting advice: skip the pleasantries, go deep, and don’t lean on your advisor slide
The Signal That Told Her She Might Need A Change
Lindsay didn’t leave Chief because the company was struggling. She left because she recognized something in herself that most founders won’t admit out loud.
“I found myself exhausted and found myself not giving 100%, kind of going down to 80, having days where I wasn’t giving even 50%, and nobody wants to be running a company and deeply invested in a company that they aren’t giving their all.”
She co-founded Chief in 2018, raised VC, and scaled a massive community for executive women through COVID and beyond. But after years of operating, she stepped back about a year ago to travel, do what she calls “a lot of soul searching,” and angel invest more formally. She also joined Next Wave, Flybridge’s operator-led scout program, a group of about 20 operators, mostly NYC-based, focused on getting first checks into startups. (See our interview with Jesse Middleton of Flybridge if you want to learn more about the program)
The Bullish connection had been building for over a decade. Lindsay has known co-founders Mike and Brent since before Bullish even existed. Over the past year, their conversations about how consumer behavior has shifted, how audiences have democratized brands, and what she calls this “weird post-post modern era” of consumer, kept getting deeper.
“We just had these amazing conversations that went from deep, interesting, meaty dialogue into we should be doing this together. We should actually be partnering.”
The Venture Partner role lets her focus on deal flow through her New York operator and founder network, while working across both sides of Bullish: the consumer VC side and their agency/brand side. And she’s still participating in Next Wave (which has an AI thesis and focuses on pre-seed), while Bullish writes bigger seed-stage checks in consumer.
What She’s Investing In
Lindsay’s angel portfolio gives a clear picture of what catches her eye. A few examples:
- Riley is an AI-powered parenting co-pilot for new parents and moms. Parenting is a crowded category, but Lindsay saw “an incredible founder with an interesting wedge.”
- Rocco is a smart fridge (yes, it was on Shark Tank) founded by Elise Borkin. Lindsay describes it as “a viral Instagram darling” with genuine consumer love.
- Sifsy is a B2B tool that analyzes comment section data so CMOs and brand teams can actually interpret what their audience is saying.
If you look across all three, they’re either products that create a strong relationship with the end user or tools that help brands decode that relationship. Lindsay’s taste skews consumer tech over CPG, and she’s drawn to founders “doing weird things” in non-obvious categories rather than me-too plays in crowded markets.
Beyond her current portfolio, Lindsay called out a few areas she’s watching closely.
- The loneliness epidemic and niche communities. After building Chief, she still sees massive opportunity in how people connect and find belonging. She specifically called out the male loneliness epidemic as “fascinating” and said she believes there’s still a lot of innovation ahead.
- Women’s health across the full lifecycle. She’s aware there are many companies right now addressing perimenopause and menopause, but she’s interested in more holistic approaches that span a woman’s entire health journey, not just one life stage.
She also thinks there’s something to be looked at more deeply regarding the trend of companies bringing in expensive AI consultants to squeeze efficiencies out of their teams. Point blank: She thinks they’re looking at it the wrong way.
“We really need to understand how it’s going to revolutionize the businesses and how the business model needs to change and flex. It’s almost been used as a wedge with HR (regarding making) teams work differently when in fact people need to understand that their business model (in a post AI world) needs to flex and change”
Skip The Small Talk
Lindsay was refreshingly blunt about what makes meetings memorable and what doesn’t.
“I want to avoid the 10 minutes of small talk. I think small talk is really boring. Like you really don’t need to remember where I live or what my kids’ names are.”
What she actually values: “a deep meaty, interesting, weird conversation that I will walk away with and make me think differently about a category, about how I’m investing, about the way people are interacting with brands.”
If you’re building in consumer tech, community, women’s health, or using AI to rethink a consumer category, Lindsay is someone worth reaching out to. Just skip the pleasantries 🙂
The full conversation with Lindsay goes deeper into her Chief journey, how the Next Wave scout program works, and what she’s looking for in her first deals at Bullish. Watch the full interview above to get the complete picture.
