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/

Jaksot(1178)

Meta's Layoff Math, FedEx's Agent Army, & A Crazy AI Productivity Forecast

Meta's Layoff Math, FedEx's Agent Army, & A Crazy AI Productivity Forecast

March 17, 2026: Five major AI models shipped in a single week in February. Your company's training budget grew 5%. Cathie Wood told Bloomberg this morning that AI is already pushing productivity above...

17 Maalis 52min

The New Rules for People Leaders in an AI-Integrated Workplace - Emily Field, Chief People Officer of LPL Financial

The New Rules for People Leaders in an AI-Integrated Workplace - Emily Field, Chief People Officer of LPL Financial

Many managers today spend more time on paperwork and individual tasks than actually coaching their teams. This lack of true leadership hurts the employee experience and stops a business strategy from ...

16 Maalis 53min

The Hidden Cost of AI Nobody Is Counting & Why Tesla Is Hiring While Others Are Firing

The Hidden Cost of AI Nobody Is Counting & Why Tesla Is Hiring While Others Are Firing

March 13, 2026: Most companies are cutting headcount to fund AI — but do they actually know what AI costs? When agentic AI runs autonomously overnight, the compute bill can hit $120,000 to $270,000 a ...

13 Maalis 38min

Why Companies Only Talk About AI Fear And Never the Opportunity

Why Companies Only Talk About AI Fear And Never the Opportunity

March 12, 2026: Companies are failing to communicate the real promise and potential of AI to their people. Sam Altman stood in front of BlackRock and admitted nobody knows what to do about the labor-c...

12 Maalis 43min

Amazon Workers Say AI Is Making Their Jobs Harder, Oracle Confirms AI Layoffs, and the Safety Net Isn't Ready

Amazon Workers Say AI Is Making Their Jobs Harder, Oracle Confirms AI Layoffs, and the Safety Net Isn't Ready

March 11, 2026: Amazon corporate workers say the company's AI push is creating more work, not less — with surveillance dashboards tracking every click and promotion criteria now tied to AI adoption. O...

11 Maalis 38min

Hired to Train Your Replacement, Bosses Stealing AI Time, and the CEO Headcount Formula Nobody's Talking About

Hired to Train Your Replacement, Bosses Stealing AI Time, and the CEO Headcount Formula Nobody's Talking About

March 10, 2026: AI is generating real, measurable productivity gains at major companies. Workers aren't seeing any of it. A new survey of 100 major CEOs finds only 9% plan to cut jobs because of AI th...

10 Maalis 48min

How Lumen Is Preparing Leaders for Humans + AI Agents (w/ EVP & CPO Ana White)

How Lumen Is Preparing Leaders for Humans + AI Agents (w/ EVP & CPO Ana White)

While many companies focus only on buying new AI tools, the real secret to success often lies in changing how leaders think and act to drive a massive business turnaround. In this episode, Anna White,...

9 Maalis 51min

The February Jobs Disaster, the Uber Culture War, and Why Enterprise AI Is Still Mostly Hype

The February Jobs Disaster, the Uber Culture War, and Why Enterprise AI Is Still Mostly Hype

March 6, 2026: The U.S. economy lost 92,000 jobs in February — and the headline number is almost the least interesting part of the story. When you break down where the losses actually came from, you g...

6 Maalis 42min

Suosittua kategoriassa Liike-elämä ja talous

sijotuskasti
mimmit-sijoittaa
rss-rahapodi
psykopodiaa-podcast
rss-rahamania
rss-sisalto-kuntoon
ostan-asuntoja-podcast
rss-lahtijat
hyva-paha-johtaminen
rss-startup-ministerio
rss-sami-miettinen-neuvottelija
rss-seuraava-potilas
lakicast
herrasmieshakkerit
leadcast
rahapuhetta
rss-porssipuhetta
rss-rentotapaus
rss-tyoelamasta-podcast
rss-viisas-raha-podi