How did Joe Thomas and his co-founders keep building Loom when they had maxed-out credit cards and only 14 days of runway left?

Before Loom became one of the most recognizable asynchronous video platforms, Joe Thomas, Vinay Hiremath, and Shahed Khan spent nine months testing ideas, making major pivots, and listening closely to early users. Their persistence eventually transformed a struggling user-feedback product into a new way for people to communicate at work.

In this encore episode of From Start-Up to Grown-Up, executive coach and bestselling author Alisa Cohn sits down with Joe to explore Loom’s earliest days, the approximately 100 fundraising rejections that strengthened his pitch, and the leadership lessons he learned while scaling the company.

Joe also reveals why Loom defined its values when the team had only seven people, how meditation helped him make better decisions, and why founders must become comfortable doing the work they would naturally rather avoid.

This is a candid conversation about resilience, fundraising, company culture, asynchronous leadership, and what it takes to grow from founder to CEO.

You’ll learn:

How Joe Thomas and his co-founders discovered the idea for Loom
How Joe improved his fundraising skills after approximately 100 rejections
Why founders often avoid the responsibilities that make them uncomfortable
How Loom defined its company values with only seven employees
Why values become most important during difficult decisions
How meditation helped Joe become less reactive as a leader
Why giving difficult feedback can be an act of belief
How leaders can protect their energy while building a company
When to communicate asynchronously and when to hold a meeting
Why discomfort is an unavoidable part of growing into a leader

We talk about:

00:00 Meet Joe Thomas, co-founder of Loom

01:27 The original idea behind video communication at work

04:20 Nine months of experimentation, customer conversations, and pivots

10:17 Starting the company with $25,000 and a mattress on the floor

12:20 Reaching the final 14 days of runway

16:17 Learning to fundraise after approximately 100 rejections

19:44 Choosing investors for a long-term relationship

22:01 Tracking time and prioritizing a founder’s responsibilities

31:43 Defining Loom’s values with only seven employees

42:13 How meditation improved Joe’s decision-making

46:13 Balancing empathy with difficult feedback

50:33 Becoming friends with hard times

51:28 Why taking care of yourself makes you a better CEO

57:10 When to use asynchronous communication instead of a meeting

01:01:04 Learning to live with imposter syndrome

01:03:28 What Joe wishes he had understood earlier

01:05:16 Joe’s advice for founders growing into leaders

Follow Joe on

LinkedIn: https://www.linkedin.com/in/joethomasx/

Connect with Alisa!

Follow Alisa Cohn on

Instagram: @alisacohn
Twitter: @alisacohn
Facebook: facebook.com/alisa.cohn
LinkedIn: https://www.linkedin.com/in/alisacohn/
Website: http://www.alisacohn.com

Download her 5 scripts for delicate conversations (and 1 to make your life better)

Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

126: Joe Thomas Took Loom From 14 Days of Runway to a $1B Acquisition [ENCORE]

From Start-Up to Grown-Up

126: Joe Thomas Took Loom From 14 Days of Runway to a $1B Acquisition [ENCORE]