Behind The Scenes At Freshbooks: "Blind Dates" With Coworkers, Creating A Secret Competitor, Being The Longest Living Cocktail Party, And Much More

Behind The Scenes At Freshbooks: "Blind Dates" With Coworkers, Creating A Secret Competitor, Being The Longest Living Cocktail Party, And Much More

Mike McDerment is the founder and CEO of FreshBooks, the world's #1 cloud accounting software for self-employed professionals. Headquartered in Toronto, Canada, it was built in 2003 after he accidentally saved over an invoice. McDerment spent 3.5 years growing FreshBooks from his parents' basement. Since then, now with around 300 employees, over 10 million people have used FreshBooks to save time billing, and collect billions of dollars.

McDerment mentioned that an employee at Freshbooks told him that the culture of the company feels like summer camp and that is something McDerment is thrilled about. Why?

When a child comes home from summer camp, they are mentally and emotionally fit. They have been challenging themselves all week – both physically and mentally. This produces a very high level of self-esteem and excitement. This is what they want employees at Freshbooks to experience each day. They believe it will lead to a sense of personal growth and self-esteem.

The culture of Freshbooks works to be like the 'longest living cocktail party on earth.' Why?

Generally, when you go to a cocktail party you have been invited by someone you like. There you will find some people you know and others you don't. This environment creates a feeling safety and of being welcome.

One of the ways they have worked to create this culture is to set up people on professional blind dates – in groups of 3 or 4. They ask employees if they would like to participate and then they match up employees who normally would not connect with on another on a day to day basis. This is one way to help the company feel smaller no matter how much they grow in size.

One piece of advice McDerment gives to larger organizations is to focus on reinforcing the behaviors you want perpetuated. Make sure to celebrate those things.

What you will learn in this episode:

  • What it is like to work at Freshbooks
  • What the movie 'Elf' has in common with the culture at Freshbooks
  • Why has Freshbooks won awards for 'best place to work'
  • Why they created a secret competitor company
  • How to keep your company feeling small no matter the size

Contact:

LinkedIn: https://www.linkedin.com/in/mike-mcderment-68895a1/

Episoder(1184)

The CEO AI Paradox, Job Hugging, and Why Electricians Are the Hottest Job in Tech

The CEO AI Paradox, Job Hugging, and Why Electricians Are the Hottest Job in Tech

March 3, 2026: The hype around AI and jobs is loud. The actual data tells a more nuanced story. This week, Stanford economist Nick Bloom released the most rigorous study yet on AI's impact on employme...

4 Mar 37min

Solving the $2 Trillion Student Debt Crisis with U.S. News & World Report CEO Eric Gertler

Solving the $2 Trillion Student Debt Crisis with U.S. News & World Report CEO Eric Gertler

Many parents and leaders are wondering if a college degree is still worth the high educational costs. With student debt reaching nearly $2 trillion and the AI impact changing the future of work, the t...

2 Mar 48min

Jack Dorsey Just Fired 40% of His Company. Stock Soared 24%. He Says You're Next

Jack Dorsey Just Fired 40% of His Company. Stock Soared 24%. He Says You're Next

February 27, 2026: Jack Dorsey cuts 40% of Block's workforce — 4,000 jobs — credits AI, and predicts most companies will follow within a year. We do a deep dive on whether this is genuine AI transform...

27 Feb 38min

Engineers Are Burning Out, Young Workers Are Shut Out, and Trade Schools Are Suddenly Elite

Engineers Are Burning Out, Young Workers Are Shut Out, and Trade Schools Are Suddenly Elite

February 26, 2026: Engineers are facing a productivity panic as coding agents accelerate output — and pressure — at the same time. Nvidia just posted a staggering quarter, underscoring how fast the in...

26 Feb 36min

Anthropic Abandons Safety Promise, JPMorgan Replacing Workers, & The Top Skills for 2026

Anthropic Abandons Safety Promise, JPMorgan Replacing Workers, & The Top Skills for 2026

February 25, 2026: This week Anthropic — one of the companies most associated with responsible AI — gutted the safety commitment it made in 2023. The same week the Pentagon gave its CEO a Friday ultim...

25 Feb 37min

Anthropic Moved Into Your Office, the Fed Admitted It Can't Help, and Goldman Said It Was All for Nothing

Anthropic Moved Into Your Office, the Fed Admitted It Can't Help, and Goldman Said It Was All for Nothing

February 24, 2026: Five major stories broke in the last 24 hours at the intersection of AI and the future of work — and they're all in conversation with each other. Anthropic launched Claude directly...

25 Feb 47min

Why the Frontline Workforce Is the Future of Work (And How Spectrum Is Proving It)

Why the Frontline Workforce Is the Future of Work (And How Spectrum Is Proving It)

Many companies try to solve low morale with simple perks like wellness apps, but workers often care more about real pay and career growth. The big challenge today is keeping frontline employees happy ...

23 Feb 51min

The Robot Is Already Your Boss. Here Are the Rules It Should Follow

The Robot Is Already Your Boss. Here Are the Rules It Should Follow

Feb 20, 2026: AI is already deciding who gets hired, promoted, and fired — and there are almost no rules governing how it does any of that. In this episode, I'm building those rules. I call them the ...

20 Feb 1h 1min

Populært innen Business og økonomi

stopp-verden
lydartikler-fra-aftenposten
dine-penger-pengeradet
e24-podden
rss-borsmorgen-okonominyhetene
rss-penger-polser-og-politikk
pengepodden-2
livet-pa-veien-med-jan-erik-larssen
finansredaksjonen
utbytte
pengesnakk
stormkast-med-valebrokk-stordalen
tid-er-penger-en-podcast-med-peter-warren
morgenkaffen-med-finansavisen
liberal-halvtime
rss-sunn-okonomi
lederpodden
rss-pa-konto
rss-investering-gjort-enkelt
rss-markedspuls-2