Pitching investors: iterating through 100 rejections

Melanie Perkins is CEO and co-founder of Canva, currently valued at over $42 billion, generating over $3 billion in annual revenue, with more than 240 million monthly active users and, incredibly, eight consecutive years of profitability. But the journey was far from smooth. Melanie was rejected by over 100 investors during her first fundraising round, her team spent two years without being able to ship a new feature during a technical rewrite, and the company pivoted early from a yearbook publishing platform to become the design powerhouse it is today. Through it all, she maintained what she calls “column B” thinking: building toward a dream future rather than just using the bricks around you.

We discuss:

1. How “column B” thinking helped Melanie build Canva, by starting with an impossible vision rather than existing constraints

2. The power of setting “crazy big goals”

3. How Canva survived a painful two-year period without shipping any new features while rewriting their codebase

4. How Melanie pushed through 100 investor rejections, and how she used each rejection to strengthen her pitch

5. Canva’s “two-step plan”: build one of the world’s most valuable companies, then do the most good possible

6. Melanie’s vision for 2050 and why she believes imagination is the first step toward a better world

—

Brought to you by:

Vanta—Automate compliance. Simplify security. https://vanta.com/lenny

Stripe—Helping companies of all sizes grow revenue: https://stripe.com/

Justworks—The all-in-one HR solution for managing your small business with confidence: https://ad.doubleclick.net/ddm/trackclk/N9515.5688857LENNYSPODCAST/B33689522.424104489;dc_trk_aid=616485033;dc_trk_cid=237010502;dc_lat=;dc_rdid=;tag_for_child_directed_treatment=;tfua=;gdpr=$

—

Transcript: ⁠https://www.lennysnewsletter.com/p/the-making-of-canva⁠⁠

—

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/176082995/my-biggest-takeaways-from-this-conversation

—

Where to find Melanie Perkins:

• X: https://x.com/melaniecanva

• LinkedIn: https://www.linkedin.com/in/melanieperkins/

—

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

—

In this episode, we cover:

(00:00) Introduction to Melanie Perkins and Canva

(04:44) Building a “column B” company

(06:36) Operationalizing big visions

(13:13) Crazy big goals and celebrations

(22:00) Challenges and setbacks in Canva’s journey

(26:30) Fundraising and investor rejections

(29:36) Leadership and growth lessons

(34:38) Canva’s goal-driven structure

(35:46) Balancing work and personal life

(38:02) Community-driven product development

(40:37) The two-step plan for global impact

(45:04) Canva’s biggest launch yet

(48:10) How Canva approaches product expansion

(52:37) AI integration in Canva

(53:56) AI corner

(55:22) Melanie’s vision for 2050 and beyond

(01:00:07) Lightning round and final thoughts

—

Referenced:

• Canva: https://www.canva.com/

• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach

• Building high-performing teams | Melissa Tan (Webflow, Dropbox, Canva): https://www.lennysnewsletter.com/p/building-high-performing-teams-melissa

• UserTesting: https://www.usertesting.com/

• Figma: https://www.figma.com/

• Adobe: https://www.adobe.com/

• Calm: https://www.calm.com/

• Gandhi’s quote about happiness: https://www.brainyquote.com/quotes/mahatma_gandhi_105593

• Help us improve Canva: https://www.canva.com/help/get-in-touch/general-feedback/

—

Recommended books:

• Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration: https://www.amazon.com/Creativity-Inc-Expanded-Overcoming-Inspiration/dp/0593594649/

• The Lean Startup: How Today’s Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses: https://www.amazon.com/Lean-Startup-Entrepreneurs-Continuous-Innovation/dp/0307887898/

• The Power of Moments: Why Certain Experiences Have Extraordinary Impact: https://www.amazon.com/Power-Moments-Certain-Experiences-Extraordinary/dp/1501147765

• Designing the Obvious: A Common Sense Approach to Web and Mobile Application Design: https://www.amazon.com/Designing-Obvious-Common-Approach-Application/dp/0321749855

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.