20VC: Raising $60M and Not Touching a Dollar of It; The 3 Decisions That Led to a Cash-Flow Positive Business, Why Not Being Able To Fundraise in the Early Days Can Help Build Your Business & What are the First Things To Break in Scaling Orgs with Sameer Shariff, CEO @ Cambly

Sameer Shariff is the Co-Founder and CEO @ Cambly, the company that allows you to become fluent faster through one-on-one video chat lessons with native English tutors. To date, Sameer has raised over $60M with Cambly from the best including Jeremy Levine @ Bessemer, Sarah Tavel @ Benchmark, Monashees, YC and more. Prior to founding Cambly, Sameer spent close to 5 years at Google on the Search Quality team and became the Tech Lead of the Search experiments team helping make experimentation a core part of the launch process.

In Today’s Episode with Sameer Sharif We Discuss:

1.) Entry into Startups and Co-Founding Cambly:

• How did Sameer make his way into the world of tech with his joining Google straight out of college?

• What were the 1-2 biggest takeaways from his time at Google? How did it shape his mindset?

• What was the a-ha moment for Sameer with Cambly?

2.) The Trials and Tribulations of Leadership:

• What does “high performance” mean to Sameer in business? How has it changed over time?

• What are the first things to break in a scaling company?

• How do the best companies retain speed and agility with scale?

• What are the single biggest hiring mistakes Sameer has made? What did he learn?

3.) The Fundraise that Led to Cash Flow Positive:

• Why does Sameer think it was so hard to fundraise for Cambly in the early days?

• When they failed to raise their Series A, what 3-4 core decisions did they make to get Cambly to cash flow positive as fast as possible?

• How did Sameer communicate their failed fundraising to the team? How did he do this in a way that rallied the troops and did not worry or scare them?

• What was the tipping point for fundraising to become much much easier for the company?

• Given they have not touched any of their Series A or Series B funds, how does Sameer think about the balance of growth vs profitability?

4.) Marketplace Dynamics 101:

• How did Cambly acquire the first 100 customers on the demand side?

• What is the most challenging dynamic of Cambly; demand or supply side?

• Where does Sameer see most marketplace founders make the biggest mistakes?

• What does Sameer know now on the intricacies of marketplace dynamics that he wishes he had known at the beginning?

Items Mentioned In Today’s Episode with Sameer Shariff:

Sameer’s Favourite Book: The Most Human Human: What Artificial Intelligence Teaches Us about Being Alive