My guest today is Isaac Saldana, co-founder and former CEO of Sendgrid, the API centric email platform which went public in 2017 and was acquired by Twilio for 3 billion in 2019.
Before Sendgrid, Isaac started multiple startups that failed and faced a ton of challenges as a first time founder, with very little business background and an introverted personality.
Today, we discussed Isaac’s challenges in transitioning from founder to CEO, his decision to bring in an external CEO to SendGrid, and the lessons he learned along the way. We also covered the company-building lessons he gained at SendGrid, including insights on product development, market timing, and team building.
Finally, we talked about his latest venture, Memo, and how he aims to empower introverts to build their personal brands and social capital in a world dominated by social media.
Spotify | YouTube | Apple Podcasts
🗒 Show notes:
[04:01] - How did Isaac decide to bring in an external CEO
[09:18] - Transition from founder to becoming a CEO
[19:01] - The role of the founder
[29:51] - Business lessons from SendGrid's success
[51:19] - What does it mean to build a social network platform for introverts
🧠 Key Takeaways
#1 Hire Your Boss: Isaac knew early on he wasn’t the ideal long-term CEO, preferring to focus on product development. Supported by mentors and being the transparent with the board, he successfully transitioned leadership to Jim Franklin, who shared the company’s core values and mentored Isaac, ensuring both his growth and SendGrid’s success.
#2 Building a Strong Foundation: Isaac emphasized the importance of a great team, mentors, and clear values. He learned that even with a solid team and funding, success isn't guaranteed. Mentors help navigate unknown challenges, and strong values guide decisions when mentors can't.
#3 Empowering the Quiet Majority: Isaac's Memo is a social network for introverts, tackling the issue that 90% of social media content is created by 10% of users. Memo focuses on meaningful connections, allowing users to be found on their terms, prioritizing user control and privacy over invasive engagement tactics.
#3 Empowering the Quiet Majority: Isaac's Memo is a social network for introverts, addressing the issue that 90% of social media content is created by 10% of users. Memo focuses on meaningful connections, allowing users to be found on their terms, prioritizing user control and privacy over invasive engagement tactics.
😲You won’t hear this anywhere else
[About hiring an external CEO] “I think I would start with the end: hire your boss. You need to see this person as your boss, even though you created the company and have many ideas. Ultimately, they need the ability to make the decisions required for a CEO.
Accepting this makes everything easier. A smart CEO will always seek the founder's opinion, especially on gut feelings. Founders have the best gut instincts for their company by far. If CEOs leverage this, you can create a great relationship where the founder feels included in decisions.”
🎧 From Immigrant to a $3B Exit: The Story of Sendgrid