Logo
Sign in
Sign in
Join Free
Home
Originals
News
Events
The Stack
Founder Community
Contact us

Simon Hartley | Wumdrop

What selling grilled cheese sandwiches online can teach you about selling a company to Walmart.

What can delivering toasted cheese sandwiches teach you about building a startup?

In this episode of How Would You Build It, we talk with Simon Hartley, co-founder of Wumdrop, about the journey from scrappy beginnings to a successful exit to Massmart.

Simon shares the quirky story of how he and his co-founder first tested logistics by delivering sandwiches, what it’s really like to integrate with a corporate giant, and the lessons founders need to know when chasing partnerships and exits.

You’ll learn:

• Why understanding corporate seasonality is key to making deals work

• Why your focus should always be on helping corporates make more money

• The hard-earned insights from a founder who’s lived the exit journey‍

Youtube

Spotify

Apple

Or skip to the highlights:

02:13 What do toasted sandwiches have to do with the Wumdrop founding story

10:06 Learning by being at the coalface

13:24 The tech that made Wumdrop stand out at the time

21:11 How to get a corporate to pay attention to your startup

27:15 Leveraging corporate seasonality

36:06 Keep your team motivated when acquired by corporate

41:36 Corporate Seasonality

KEEP READING

Simon Hartley | Wumdrop

What selling grilled cheese sandwiches online can teach you about selling a company to Walmart.

What can delivering toasted cheese sandwiches teach you about building a startup?

In this episode of How Would You Build It, we talk with Simon Hartley, co-founder of Wumdrop, about the journey from scrappy beginnings to a successful exit to Massmart.

Simon shares the quirky story of how he and his co-founder first tested logistics by delivering sandwiches, what it’s really like to integrate with a corporate giant, and the lessons founders need to know when chasing partnerships and exits.

You’ll learn:

• Why understanding corporate seasonality is key to making deals work

• Why your focus should always be on helping corporates make more money

• The hard-earned insights from a founder who’s lived the exit journey‍

Youtube

Spotify

Apple

Or skip to the highlights:

02:13 What do toasted sandwiches have to do with the Wumdrop founding story

10:06 Learning by being at the coalface

13:24 The tech that made Wumdrop stand out at the time

21:11 How to get a corporate to pay attention to your startup

27:15 Leveraging corporate seasonality

36:06 Keep your team motivated when acquired by corporate

41:36 Corporate Seasonality

KEEP READING

View all posts →

JOIN IN

The best stories from South Africa’s business scene. Delivered with insight, edge, and just the right amount of mischief.

Whether you’re building, scaling, operating, investing, or just curious, The Open Letter keeps you in the loop and ahead of the curve.

business

Startup Events

Founder Community

Follow us on:

© 2026 The Open Letter.
Report abusePrivacy policyTerms of use
beehiivPowered by beehiiv