Leah Busque Solivan: Founder, Leader, Creator, Backer – Below the Line with James Beshara

Key Takeaways

  • Solve a problem, don’t start a company
  • You’re much more likely to succeed as a founder when the problem you’re solving is one you’ve personally experienced before
  • When building a company, set expectations with your team from the get-go
  • Hiring advice:
    • “The more experience you have hiring people, the better you get at it”
    • Trust your intuition (it’s usually right)
      • “If there are any doubts, there are no doubts” – James
      • And realize: If you have any doubts about people, they only grow – they never go away
    • When possible, standardize the interview process to remove unconscious biases 
  • First-time entrepreneurs tend to take things more personal than they should – DON’T
  • “It seems to be so often that some of the wisest things we learn are from situations we would never have designed or designed to avoid completely” – James

Books Mentioned

  • Founders at Work by Jessica Livingston gave Leah a ton of inspiration during the early days of TaskRabbit


What were a few of Leah’s favorite parts of being a founder?

  • Leah started TaskRabbit when she was only 28-years-old shortly after leaving a job at IBM
  • “My favorite time was when we were a tiny team of 10-20 people, working out of a tiny office space”
    • TaskRabbit used to have office space at Dogpatch Labs: Pier 38 which has since been shut down (they shared space with Instagram and Twilio)
  • One of Leah’s fondest memories was the company’s appearance on Good Morning America (a 7 AM air time, meaning everyone had to be in the office at 4 AM)
    • “The phone lines were ringing like crazy… The site was going down because so much traffic was hitting it. We were completely unprepared to be on a nationally recognized news outlet. But that morning… that’s a fun memory.”

Solve a Problem, Don’t Start a Company

  • “I never set out to start a company. I was an engineer at IBM and I saw this problem that I knew how to fix… So for me, everything was really unexpected.”
    • “My passion for the product is really what perpetuated it into a company”

What does Leah look for when investing in founders?

  • They have to be building a product because they themselves are purpose-built for that opportunity
    • “I want to know when I meet a founder, why they’re sitting across from me at that moment; what life journey brought them to my office?”
    • Leah will also consider:
      • “Are they solving a problem that they’ve felt in their own lives?”
      • “Are they passionate about solving that problem?”
      • “What experience do they bring to the table?
  • What DOESN’T resonate with Leah?
    • When someone starts a company without being emotionally invested in the specific problem they’re solving

Growing Pains

  • “The bigger we [TaskRabbit] got, and the more money we raised, the harder it got for me”
  • “As we scaled and grew, it was a completely different job”
    • Leah describes her work becoming a ton of people management, investor relations management, financial modeling/budgeting, etc.
      • On people management: “You HAVE to mentor, cultivate, and invest in people and in your team to be successful, but it’s a completely different job. It’s a completely different skill set. It takes a lot of empathy. It takes a lot of time and patience. And for me, those weren’t my natural skill sets.”
        • Leah, a born software engineer, suddenly found herself managing 50 people
        • James, with Tilt, also struggled with people management – he works best as a creator

Finding Balance | Creating a High-Performance, Yet Family-Oriented, Business Culture

  • Leah was ultimately very satisfied with the familial TaskRabbit culture, but…
    • “I remember feeling that everything was great – the team was happy, everyone was friends and would often head out to happy hour, but I didn’t feel like the business was performing the way it needed to. For me, it was stressful. We had the family culture, but I always felt we should be driving more revenue and growth.”
  • If Leah were to start another company, the advice she’d give herself (and the advice she’d give to founders she’s invested in) would be:
    • “Set expectations early on. Build a high-performance team into the DNA very early and hammer that message home.”
      • Appreciate the successes, but always be looking forward to the next milestone”

Hiring Advice

  • “The more experience you have hiring people, the better you get at it”
  • Trust your intuition
    • Paul Graham once told James:
      • Young founders will make the mistake of thinking, “Oh, this is a different type of person than me, so it’s okay if we feel this distance or disconnect between us.”
      • Or – “Oh that awkwardness we feel, it must be because we have a different working style”
      • ^Don’t convince yourself of either
  • Keith Rabois once said in a tweet that within two weeks he could tell if a new team member would work out or not
    • How? By examining how often they’re at their desk and how frequently people were around them at their desk – Why?
      • In the first few weeks at a company, there’s a TON to learn – sit at your desk and get to work
      • Secondly, if everyone wants to learn from the new hire (a good sign), the new hire will attract others to their workspace
  • Two more pieces of advice:
    • “If there are any doubts, there are no doubts” – James
    • “If you have any doubts about people, they only grow. They never go away.” – James
  • When hiring executives for her portfolio companies, Leah began having advisers, other investors, and friends interview candidates to supplement any of her lapses in judgment and provide her with feedback
    • Leah would require specific questions to be asked in each interview and that each interviewer complete an evaluation afterward in Google Sheets (she created a point system where specific answers/observations were weighted differently)
      • “Standardizing the interview process takes out a lot of subjective input… Having a baseline and framework that everyone follows is very important… You can remove some of the unconscious bias in interviews by really standardizing them a bit.”

The Hardest Thing Leah Ever Had to Do

  • “The worst day at TaskRabbit was when I had to fire 30% of the team. It was like my worst nightmare had come true.”
    • (this was at the end of 2012, 4.5 years after conception – Leah was six months pregnant at the time as well)
    • TaskRabbit wasn’t running out of money, but the team needed reorganizing 
    • Leah adds:
      • “I felt like I was betraying 30% of my team. It was just awful. It was emotionally difficult for me, but I know it was so much more difficult for every person that had to go through it.”
      • “I just fail like such a failure”
      • “I think it was probably the most stressful things I’ve been through”

Don’t Take it So Personal

  • “When I was an entrepreneur for the first time, everything felt so personal… I had a heightened sense of sensitivity to everything.”
  • “Looking back, I wish I didn’t take things so personally and that I wasn’t so emotionally invested in every single moment and decision. I made it a lot harder on myself.”

Becoming a Venture Capitalist

  • During her second pregnancy, in December 2015, Leah knew it was time for a change
    • By April of 2016, Stacy Brown-Philpot became TaskRabbit CEO, and Leah became Chair of the Board
  • Around this time, IKEA reached out about acquiring the company and Leah began to think about what to do next (her new role on the board would be severely diminished if the acquisition were to go through… which it did)
    • One thing Leah knew for sure: “I didn’t want to start another company. That I was sure of.”
      • Why? – Mainly due to burnout
      • “Whatever I did next, it had to be something that allowed me to stay at the forefront from a technology standpoint”
        • Leah felt she had missed out on all the emerging technology (blockchain, AI, VR, etc.) that occurred during her 10+ year stint as TaskRabbit CEO
      • Another reason – she didn’t want to focus on only one business/technology for another decade-plus
  • So… Leah became a VC

Leah’s Favorite Aspects of Being a Venture Capitalist with Fuel Capital

  • She calls it her dream job
  • “Meeting with entrepreneurs every day is just the best thing. Just hearing about their crazy businesses and how they’re utilizing technologies to innovate and do things people have never done before… It’s just so exciting.”
  • Leah, oddly, enjoyed the aspect of raising money for TaskRabbit (James did as well with Tilt)
    • “It was a couple of weeks where you had the excuse to meet with any smart person who’ve you’ve ever admired in the tech space… It was a win, no matter how the conversation went.” – James
    • This carried over to Leah’s work as a VC and raising funds from LPs – it’s a very similar process
      • Leah says pitching as a founder is a lot more difficult. Why?
        • LPs all want the same thing (a return on their capital) – it’s much more of a math equation with them than it is with a founder trying to convince a VC to buy into their vision.
  • Chris Howard, the founder of Fuel Capital, and Leah just closed their third fund valued at $75 million
    • Chris was also an investor in James’ former company, Tilt
    • Leah says of Chris – “His empathy and ability to connect with founders is INCREDIBLE.”
      • James adds – “You’d think with investing, empathy from investors would be the easy part, but it’s so stupidly rare”
  • One of the most challenging aspects of being a VC – you get 0 immediate feedback!
    • (And because of this, you won’t have an idea if you’re good at it for quite some time
  • Leah and Chris have the philosophy – “We’re in our founder’s corner, but not in their kitchen”
    • Founders want investors that will support them but only to a certain extent
    • Leah adds – “There’s no one that knows the business better than the actual founder”
  • Fuel Capital currently has 100 portfolio companies

The 3 Stories That Have Shaped Leah as a Person | Story #1

  • Leah is half Puerto Rican – her father is from Puerto Rico
  • Leah recalls a time in high school when someone called her a racist Latin American term
    • “When he called me out in that way, everything changed in that moment. I realized I was different and didn’t look like everyone else.”
  • Why was this formative?
    • It’s made her more empathetic to unrepresented communities and minorities
      • “It’s made me focus on bringing more diversity inclusion into, not just tech, but the world in general… I came from a family that wasn’t made up of entrepreneurs… I had every reason not to be an entrepreneur and every reason to fail as an entrepreneur, but I didn’t.”

The 3 Stories That Have Shaped Leah as a Person | Story #2

  • Leah grew up as a ballet dancer and chose where she went to college based on the dance program
    • She ended up attending Sweet Briar College in Virginia – When Leah got there, she fell in love with math & computer science
  • How did knowing ballet help Leah?
    • “Ballet is very disciplined and precise. Growing up with that discipline and preciseness really aided my interest in math and computer science.”
    • The creativity aspect of ballet also helped Leah on her entrepreneurship journey

The 3 Stories That Have Shaped Leah as a Person | Story 3

  • While away at college, Leah’s mother was diagnosed with breast cancer
    • “She never complained, she was never depressed, and she never felt down about the situation. She was so optimistic and so strong all the time.”
  • “Watching her go through that with such strength and persistence, it was instilled in me as well. As I think about hard times in my life. hard times as a founder, and hard times with TaskRabbit, I definitely get my continued perseverance from my mom.”
    • James adds – “It seems to be so often that some of the wisest things we learn are from situations we would never have designed or designed to avoid completely.”

What’s a topic Leah thinks a lot about but rarely gets a chance to talk discuss?

  • How to bring up her children (now 6 and 3) in a way that they stay humble, embody the idea that nothing in life is given, and have a good work ethic
  • How do you instill that work ethic in your kids?
    • It’s a challenge – try giving your them daily chores and responsibilities around the house for a small allowance
    • Check out Bright – it’s an app James recommends which provides daily parenting tips
    • Make sure they play sports – it teaches them perseverance, discipline, and how to fail in a team setting

A Book Recommendation to Close

  • Founders at Work – it gave Leah a ton of inspiration in the early TaskRabbit days

Additional Notes

  • As CEO, Leah only took a 6-7 week maternity leave after having her first child (and it was a c-section!)
  • “One of the most traumatic things one can go through in life is to face death”
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