What if the most valuable asset you can build as an entrepreneur is not your company, but your relationships?

Jayson Gaignard built one of Canada’s largest ticket-wholesaling businesses, only to realize he had created a company he hated. When circumstances left him approximately $250,000 in debt, with a six-month-old daughter and a new marriage, he began investing in the one thing no one could take from him: his relationships.

That decision eventually led Jayson to create MMT, an invite-only entrepreneurial community built around intentional connection, carefully curated experiences, and the belief that success should never be pursued alone.

In this episode of From Start-Up to Grown-Up, executive coach and bestselling author Alisa Cohn sits down with Jayson to explore how entrepreneurs can build meaningful professional relationships, make the most of conferences, overcome social anxiety, and develop the courage to enter rooms where they do not yet feel they belong.

Jayson also shares the story behind buying 4,000 copies of Tim Ferriss’s book, his “eight seconds of courage” strategy for doing intimidating things, and the leadership decision that put nearly $2 million at risk during the pandemic.

This is a candid conversation about entrepreneurial community, relationship building, leadership, discomfort, comparison, and why proximity to the right people can change the trajectory of your life.

You’ll learn:

How Jayson turned a financial and personal crisis into a new entrepreneurial path
Why meaningful relationships are among the safest investments a founder can make
How to build an aspirational network before you have status or connections
Why attending the right events can accelerate years of relationship building
How to prepare for conferences and follow up before the excitement fades
How “eight seconds of courage” can help you move through social anxiety
Why MMT prioritizes character and connection over financial success
How Jayson made an integrity-driven decision involving nearly $2 million
Why comparison can quietly damage otherwise meaningful relationships
How founders can balance ambition with their health and long-term well-being

We talk about:

00:00 Meet Jayson Gaignard, founder of MMT and author of Community Made

03:12 Building a successful business he ultimately hated

05:00 Facing $250,000 in debt and searching for what came next

06:00 Why Jayson began investing in relationships

07:00 Buying 4,000 copies of Tim Ferriss’s book

09:16 Using regret minimization to make difficult decisions

12:00 How the right room can change your life

16:06 Building an aspirational network from scratch

22:22 How to make the most of conferences and large events

28:15 Managing social anxiety through preparation

29:45 Using eight seconds of courage to do hard things

34:07 Why personal growth requires discomfort

37:47 Building MMT as an invite-only entrepreneurial community

42:48 Leading a community like a company

45:15 Making a nearly $2 million decision during the pandemic

47:19 Why leaders cannot avoid difficult conversations

49:06 Escaping comparison and jealousy around successful peers

55:20 The long-term cost of entrepreneurial stress

56:51 Jayson’s advice for founders growing into leaders

Follow Jayson on

LinkedIn: https://www.linkedin.com/in/jaysongaignard/
Instagram: https://www.instagram.com/jaysongaignard
Website: https://www.jaysongaignard.com/
Read Community Made: The Truth About Success and the Relationships That Create It

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

127: Jayson Gaignard Was $250K in Debt. Relationships Helped Him Rebuild

From Start-Up to Grown-Up

127: Jayson Gaignard Was $250K in Debt. Relationships Helped Him Rebuild