In just over 5 years, Convoy has reached a $2.75B valuation, 1,000+ employees, and $665M raised to change the big and very complex trucking industry. What's made that possible? Grant Goodale (Co-Founder & CTO) went behind the scenes on his story and shared the principles and lessons driving Convoy's growth.

Happy Thanksgiving week. 🦃🙏Thank you to everyone who has supported this project!

I tried something different on this episode. I didn’t have a guest. I looked back at 30 interviews and shared my take on the biggest themes. This was a solo episode, but I brought in soundbites from several interviews to cover three big themes: 1. How humility looks in practice; 2. Balancing analysis with intuition; 3. Playing the long-game.

Estately grew to profitability with just over $1m raised and got acquired by Realogy. Galen Ward, CEO & co-founder, said he had no business starting the business. But he and his team made it work. He goes behind the scenes on Estately's journey, getting acquired, and his lessons from the process.

Kristen is a 2x founder, startup executive, and board member. She co-founded Onvia in 1997 which went on to IPO. Recently co-founded at Koru which sold in 2018. Now an SVP at Guild Education.

But through 25 years of building start-ups she was "operating from a place of fear."

Investors laughed at the original idea for Crowd Cow. But consumers wanted to buy right away. Now they've raised $25M, grow to 90 employees, and went from selling crowd-funded cows to a complete marketplace.

Joe Heitzeberg, co-founder & CEO, goes behind the scenes on his lessons validating and scaling Crowd Cow.

Oxygen was in trouble in 2008. Juliana Stancamiano believed it could be turned around. A decade later Juliana has written a book, she's president of the Sales Enablement Society, and her business is serving clients like Microsoft, F5, Red Bull, Starbucks, and more. She goes behind the scenes on her lessons from the turnaround.

Kelly Wright grew sales from $0 to $850M over 12 years as EVP at Tableau. Now she's a Board Director at Fastly, Lucid, Amperity, and more.

She goes behind the scenes on her leadership lessons and what really matters in company building.

Kirby Winfield is a 3x founder with 3x exits who turned VC. But his journey was not all unicorns and rainbows even after his repeated success.

He goes behind the scenes on his path to finding love in the game, what he looks for in startups, and his unique approach to investing in founders at Ascend.vc.

20 years as a VC at Madrona. Headline IPOs like Accolade, Smartsheet, Apptio, Isilon. Invested in cloud before it was cool. 3x Midas list. 3x CB's top 100 VC list. Matt goes behind the scenes on his lessons (from the highs and lows), Madrona's philosophy, and how the best leaders work.

Esper 2x'd revenue during the pandemic, grew from 38 to 60 employees this year, and raised a $7.6M Series A. Yadhu Gopalan, CEO & co-founder, goes behind the scenes on Esper's pandemic shift, following his passion, and the builder's mindset.