# Calendly: Tope Awotona

- Show: [How I Built This](https://hardwarepodcasts.com/podcast/how-i-built-this)
- Published: 2020-09-14
- Length: 1h 11m
- Page: https://hardwarepodcasts.com/podcast/how-i-built-this/2020-09-14-calendly-tope-awotona

## Summary

Tope Awotona, founder of Calendly, explains how he pivoted from failed e-commerce ventures to building a $60 million/year scheduling platform after realizing the market lacked a simple, user-centric solution for complex meeting coordination. Awotona details his decision to self-fund the initial prototype by cashing in his 401(k) and maxing out credit cards, hiring the Ukrainian firm Railsware to build the MVP, and accidentally launching a free product that went viral among K-12 schools. He discusses the challenges of raising capital as a Black founder in the Southeast, securing early investment from David Commens of Atlanta Tech Village, and the strategic decision to monetize via a freemium model rather than seeking heavy VC backing.

## Chapters

- [0:00](https://hardwarepodcasts.com/podcast/how-i-built-this/2020-09-14-calendly-tope-awotona#t=0) Introduction: Tope Awotona and the Origin of Calendly
- [5:17](https://hardwarepodcasts.com/podcast/how-i-built-this/2020-09-14-calendly-tope-awotona#t=317) Early Life, Sales Experience, and Previous Business Failures
- [34:09](https://hardwarepodcasts.com/podcast/how-i-built-this/2020-09-14-calendly-tope-awotona#t=2049) Identifying the Scheduling Problem and Validating the Idea
- [41:30](https://hardwarepodcasts.com/podcast/how-i-built-this/2020-09-14-calendly-tope-awotona#t=2490) Funding the Prototype and Hiring Railsware
- [52:58](https://hardwarepodcasts.com/podcast/how-i-built-this/2020-09-14-calendly-tope-awotona#t=3178) Accidental Viral Growth and the Free Product Launch
- [58:13](https://hardwarepodcasts.com/podcast/how-i-built-this/2020-09-14-calendly-tope-awotona#t=3493) Raising Capital, Monetization, and Scaling Calendly

## Topics

- [Starting a product company](https://hardwarepodcasts.com/topic/starting-a-company)
- [Validation & product-market fit](https://hardwarepodcasts.com/topic/validation-and-product-market-fit)
- [Fundraising & investors](https://hardwarepodcasts.com/topic/fundraising)
- [Pricing, margins & unit economics](https://hardwarepodcasts.com/topic/pricing-and-unit-economics)
- [Manufacturing partners & offshoring](https://hardwarepodcasts.com/topic/manufacturing-partners)

## Most relevant to

founders before launch, early-stage companies

## Mentioned

- Calendly (product)
- Railsware (company)
- Big Green Egg (product)
- Projectorspot.com (product)
- Yardsteals.com (product)
- IBM (company)
- Perceptive Software (company)
- Atlanta Tech Village (company)

## Related episodes from other shows

- [034: Staying Motivated & Overcoming Lack of Money, Time & Skills](https://hardwarepodcasts.com/podcast/product-startup/2017-01-03-034-staying-motivated-overcoming-lack-of-money-time-skills) (Product Startup)
- [159: Build a Community to Sell Your New Product Invention](https://hardwarepodcasts.com/podcast/product-startup/2023-01-18-159-build-a-community-to-sell-your-new-product-invention) (Product Startup)
- [085: Scaling Your Product Up After Crowdfunding](https://hardwarepodcasts.com/podcast/product-startup/2021-07-21-085-scaling-your-product-up-after-crowdfunding) (Product Startup)
- [Oddball's Path From Idea to Funding a Nationwide Target Launch](https://hardwarepodcasts.com/podcast/the-startup-cpg-podcast/2026-07-11-oddballs-path-from-idea-to-funding-a-nationwide-target-launch) (The Startup CPG Podcast)
- [S3 E7: Building Bootstrapped Hardware That Sells with Christian Reed](https://hardwarepodcasts.com/podcast/the-builder-circle/2026-01-13-s3-e7-building-bootstrapped-hardware-that-sells-with-christian-reed) (The Builder Circle)

## Citing this page

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