20VC: Canva Co-Founder, Cliff Obrecht on The Journey From 100 VC Rejections to a $40BN Company, Why Good Enough is Not Good Enough, The Secret to Hiring Non-Obvious Talent and Relationships to Money and Why They Are Giving Away Billions

Cliff Obrecht is the Co-Founder & COO @ Canva, the free-to-use online graphic design tool that makes it easy for anyone to design anything from presentations to videos and social media. Cliff and Mel have scaled Canva to over 110 million monthly users, 3,500 employees, and 500,000 teams from companies like Intel and Zoom using Canva. During this incredible growth journey, they have raised over $580M with their last round valuing the company at over $40BN.

In Today’s Episode with Cliff Obrecht

1.) From Teacher to Billionaire Tech Founder:

• How did Cliff make his way into the world of tech with his founding of FusionBooks? What did the process with FusionBooks teach him about how to run Canva?

• How did the early fundraising days for Canva go? Why does Cliff think they got over 100 no’s?

• What are Cliff’s biggest pieces of advice for founders today, not in Silicon Valley, looking to raise from Silicon Valley VCs?

2.) Scaling to $40BN: The Biggest Lessons:

• What does Cliff mean when he says the secret to successful hiring is looking for “distance traveled”? How does he determine this in the interview process?

• What have been some of the single biggest lessons in what it takes to acquire the best talent?

• What are some of the biggest mistakes Cliff has made in talent acquisition? How has his process changed as a result?

• What do Canva do to get the best operators as advisors in the company? How do they compensate these advisors? What does Cliff advise founders on how to do the same?

3.) The Art of Deal-Making:

• How does Cliff think through what makes a “good deal”? How does he approach negotiation?

• What are the biggest mistakes founders make when negotiating and doing deals?

• What have been Cliff’s biggest lessons on successful investor relations over the years?

• How does Cliff and Canva approach acquisitions? What do they look for? What is their process? Why do most tech companies approach acquisitions the wrong way?

4.) Cliff Obrecht: Money, Fatherhood and Marriage:

• How does Cliff analyze his relationship to money today? How much money is enough? How has his relationship to money changed over time?

• Why have Cliff and Mel given away over $10BN to their foundation? Why is philanthropy so hard to do effectively?

• Why would Cliff hate for his children to be brought up in excess wealth?

• What does “great fatherhood” mean to Cliff? What are the most challenging aspects of parenting?

• What are the secrets to a happy marriage? How does co-founding a company with your other half work well? How does it work poorly?