# Advice Line with Tope Awotona of Calendly

- Show: [How I Built This](https://hardwarepodcasts.com/podcast/how-i-built-this)
- Published: 2026-10-29
- Length: 1h 00m
- Page: https://hardwarepodcasts.com/podcast/how-i-built-this/2026-10-29-advice-line-with-tope-awotona-of-calendly

## Summary

Tope Awotona, founder of the scheduling platform Calendly, returns to discuss the company's evolution into an AI-powered meeting assistant called Cali and the lowered barriers to building software. He advises callers on specific hardware and business challenges: Dom Cotton of New Lane struggles with profitability and scaling his UK-made foldable bike helmet; Ivana Besseluck of Playfield seeks operational systems to maintain her modular dog walking bag business while preparing for childbirth; Danny of The Nail Room weighs expansion against family life using builder gel techniques; and Justin Kitridge of ISlide prioritizes channels for his customized footwear.

## Chapters

- [0:09](https://hardwarepodcasts.com/podcast/how-i-built-this/2026-10-29-advice-line-with-tope-awotona-of-calendly#t=9) Introduction: Tope Awotona and Calendly's AI Pivot
- [5:15](https://hardwarepodcasts.com/podcast/how-i-built-this/2026-10-29-advice-line-with-tope-awotona-of-calendly#t=315) Building Software with Low Capital and AI Tools
- [7:40](https://hardwarepodcasts.com/podcast/how-i-built-this/2026-10-29-advice-line-with-tope-awotona-of-calendly#t=460) New Lane: Scaling the UK-Made Foldable Helmet
- [19:12](https://hardwarepodcasts.com/podcast/how-i-built-this/2026-10-29-advice-line-with-tope-awotona-of-calendly#t=1152) Playfield: Maintaining Momentum During Maternity Leave
- [33:11](https://hardwarepodcasts.com/podcast/how-i-built-this/2026-10-29-advice-line-with-tope-awotona-of-calendly#t=1991) The Nail Room: Balancing Expansion and Family
- [44:29](https://hardwarepodcasts.com/podcast/how-i-built-this/2026-10-29-advice-line-with-tope-awotona-of-calendly#t=2669) ISlide: Prioritizing Sales Channels for Growth

## Topics

- [Crowdfunding & preorders](https://hardwarepodcasts.com/topic/crowdfunding)
- [Direct-to-consumer & e-commerce](https://hardwarepodcasts.com/topic/direct-to-consumer)
- [Pricing, margins & unit economics](https://hardwarepodcasts.com/topic/pricing-and-unit-economics)
- [Scaling production](https://hardwarepodcasts.com/topic/scaling-production)
- [AI & machine learning](https://hardwarepodcasts.com/topic/ai-and-machine-learning)
- [Validation & product-market fit](https://hardwarepodcasts.com/topic/validation-and-product-market-fit)

## Most relevant to

early-stage companies, companies scaling up

## Mentioned

- Calendly (product)
- Cali (product)
- New Lane (product)
- Playfield (product)
- The Nail Room (product)
- ISlide (product)
- Shopify (tool)
- Chewy (company)
- Fanatics (company)
- Dry Bar (product)
- Regal Nails (company)
- Nike (product)
- Adidas (product)
- Lovable (tool)
- Replit (tool)

## Related episodes from other shows

- [97: Plateaus](https://hardwarepodcasts.com/podcast/thoroughly-considered/2023-04-06-97-plateaus) (Thoroughly Considered)
- [#194 - AI for Ops with YANY Beauty and Phenomenal Foods Co](https://hardwarepodcasts.com/podcast/the-startup-cpg-podcast/2025-04-29-194-ai-for-ops-with-yany-beauty-and-phenomenal-foods-co) (The Startup CPG Podcast)
- [75: We Got to Finish Something](https://hardwarepodcasts.com/podcast/thoroughly-considered/2021-12-16-75-we-got-to-finish-something) (Thoroughly Considered)
- [Episode 336: Take the hug…](https://hardwarepodcasts.com/podcast/making-it/2021-12-24-episode-336-take-the-hug) (Making It)
- [92: We’ve Hit Our Ceiling](https://hardwarepodcasts.com/podcast/thoroughly-considered/2023-01-12-92-weve-hit-our-ceiling) (Thoroughly Considered)

## Citing this page

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