Scott Gilmour helped take APEX Surety & Insurance Ltd from a scrappy startup to a thriving insurance business. This is his story.

In this episode of Winning in Winnipeg, I speak with Scott Gilmore, founding partner of Apex Surety and Insurance. Scott shares his transformative journey from corporate law to the insurance industry, recounting his many failures and insights along the way.

Scott shares his experience managing large construction projects, launching APEX during the COVID-19 pandemic, and the importance of strong client relationships. He also reflects on family dynamics, the business landscape in Winnipeg, community growth, and offers advice for young professionals.

Scott is an incredibly intelligent and scrappy entrepreneur whose insights about startups, entrepreneurship, insurance, city planning and the evolving market in Winnipeg are invaluable! Enjoy the conversation!

Follow @thewinninginwinnipegpodcast for more incredible conversations with the BEST in Winnipeg!

// CHAPTERS //

00:00:00 - Take Risks While You're Young

00:00:26 - Introducing Scott Gilmour

00:04:05 - APEX Surety & Insurance

00:06:47 - Time in Toronto

00:07:56 - Growing APEX From the Ground Up

00:14:20 - Why Law and Why Insurance?

00:31:20 - The Hardest Part of Starting VS Running

00:38:44 - Biggest Results

00:45:44 - Common Misconceptions about Insurance

01:01:05 - Biggest Failures

01:02:03 - Advice to Younger Entrepreneurs

01:10:50 - Managing the Work/Life Balance

01:20:08 - Location of Clients

01:21:54 - The Firefighter Life

01:24:25 - The Future of Winnipeg

01:33:08 - Clients Outside of Winnipeg

01:35:45 - Biggest Personal Influences

01:38:03 - The Value of Winnipeg

01:42:48 - Contact Scott Gilmour!

\\ GUEST LINKS \\

Website: https://www.apexsurety.ca/

LinkedIn: https://ca.linkedin.com/in/scott-gilmour-apex-surety

********************

FOLLOW THE WINNING IN WINNIPEG PODCAST!

Follow @thewinninginwinnipegpodcast for more!

\\ SOCIAL \\

Instagram: https://www.instagram.com/thewinninginwinnipegpodcast/

TikTok: https://www.tiktok.com/@winninginwinnipeg?_t=8bgg2yE4MKL&_r=1

Facebook: https://www.facebook.com/winninginwinnipeg?mibextid=LQQJ4d

YouTube: https://www.youtube.com/channel/UCdS1VVdejoxRlh2HXkw3UoA

\\ LISTEN \\

Spotify: https://open.spotify.com/show/4ZTEyelsxoSO5gH2OArmVg?si=6ad88429dffe46ea

Apple Podcasts: https://podcasts.apple.com/ca/podcast/the-winning-in-winnipeg-podcast/id1639621311

IHeart Radio: https://www.iheart.com/podcast/269-the-winning-in-winnipeg-bu-87292041/

Podbean: https://wpgbusiness.podbean.com/

YouTube: https://www.youtube.com/channel/UCdS1VVdejoxRlh2HXkw3UoA

@thewinninginwinnipegpodcast your premier business podcast, featuring great conversations with local entrepreneurs, business owners, and other celebrities who are absolutely killing it! Learn who they are, and what makes them tick, and get an inside look into the ins and outs of their unique industries.

Follow @thewinninginwinnipegpodcast so you don't miss a single episode!

\\ EMMETT LEO HOMES \\

Dan Nagy is the founder of Emmett Leo Homes, a luxury custom home-building company in Winnipeg, Manitoba. He is also the face of @EmmettLeoHomes YouTube, where he shares insights into everything custom home building to empower viewers to be more equipped to tackle their own projects.