Advice from a $250M CEO, Advice from a $28B CEO - Tactician #0036

16/01/2024

ADVICE FROM A $250M CEO

Turner Novak, Investor at Banana Capital interviews Sid Yadav, CEO & Co-founder at Circle in “Immigrant to $250M CEO: How Circle Powers the Creator Economy with CEO and Co-founder Sid Yadav”

• Embrace Remote Work and International Hiring:

  • "We hire globally. We comp people according to maybe Tier 2 US cities... I never understand why any startup would want to compete in that talent pool when there's literally the entire world you could hire from."

• Utilise Founder CEOs as Mentors or Coaches:

  • "I found founders to be the most honest and altruistic people in terms of how they go about giving and sharing advice. Investors and folks in your team even, even your co-founders at times just do not have that level of maybe exposure and honesty to do that as do seasoned founders and CEOs."

• Leveraging Community for Customer Support:

  • "What’s great, by the way, about a community in the early days is you’re also helping scale customer support, because [...] they can share their question and maybe someone else, another customer, may help them out. Or maybe they can look up whatever their issue is and find a post that someone else made who had the same problem or same question and got resolved"

• On Ensuring Meetings are Productive and Necessary:

  • "Remote forces you to think what is it that should be async? What is it that should be sync? [...] Because in a well run company where people are documenting stuff, people are sharing updates async, there’s less to meet about. What I like to do is I like to make my meetings as fun and meaningful as possible. It has to feel like the opposite of a boring status update. It has to feel fruitful when you’re in there."

• On Striving for Financial Independence and Control of Your Destiny:

  • "There’s nothing better than owning your destiny, being cashflow positive to ourselves, to the investors, to everyone involved. [...] So, I’ve just set that constraint up for the company that we’re going to be cashflow positive no matter what. Now, whether or not we grow 90% next year or 85% or 100%, I don’t know, but we’re going to try and grow as fast as we can with that constraint.”

• Avoid Self-Delusion and Stay Grounded in Reality:

  • "Don’t bullshit yourself. Don’t get high on your own supply. Question yourself. Be super humble. Be transparent. Get all of the feedback and stay relevant. Stay true to yourself because I really feel like a lot of the downfall and the downward spirals, a lot of those situations stem from a founder who’s just not been very honest with themselves for many months or many years."

• Use ChatGPT as a Sparring Partner for Ideation:

  • "I use it honestly as a sparring partner where I will tell ChatGPT about what I’m thinking and how I’m thinking about it. I will ask it to respond to me and critique my ideas."

ADVICE FROM A $28B CEO

Harry Stebbings, Founder at 20VC interviews Brian Halligan, Co-founder at HubSpot In 20VC: Hubspot Co-Founder Brian Halligan on Leadership Lessons Scaling Hubspot to a $28BN Market Cap?“

• Embrace and Leverage Your Quirkiness:

  • Insight: Embracing personal quirks can attract the right people and set a unique culture for your company.

  • Quote: "I tried to start being myself after that and it paid off. Trying to be somebody else has a lot of overhead to it."

• On Hiring for Fit Over Brand:

  • "What you want is somebody who's three years up the ice cliff from you who's struggled through that same path... not just the logo like I think it's okay if you hire someone from a much much bigger company if they have climbed up that ice cliff and they have seen the lessons."

• Recognize the Challenges of Leadership Evolution:

  • Insight: As your company scales, evolving your leadership style is crucial, including shifting from control to delegation.

  • Quote: "The control freakness of Founders... turns into an amazing weakness as you scale and you're more prepared than everyone, you're overthinking and you're basically doing everyone else's job."

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