How do you scale from 3 to 100+ employees while preserving the collaborative spirit that made you successful in the first place? 

In this engaging episode of The Learn-It-All Podcast, Colton Pace shares his journey from managing billionaires' assets to founding OwnWell, a rapidly growing startup that helps homeowners reduce their property expenses. He discusses how his experience in wealth management revealed opportunities to democratize financial tools previously available only to the ultra-wealthy. Pace offers valuable insights on building strong co-founder relationships, creating an office-first culture that promotes cross-functional learning, and maintaining effective communication as an organization scales. 

This Episode Covers: 

• Why having multiple co-founders with complementary skills is crucial for startup success 
• The importance of over-communication when scaling from a small team to 100+ employees 
• How to maintain productive conflict between founders without damaging relationships 
• Why intellectual curiosity should be a key hiring criterion 
• Creating opportunities for cross-functional learning through shadowing and lunch-and-learns 
• The value of testing ideas with real customers before building perfect solutions 
• Managing founder finances and expectations during the early startup phase 
• Balancing in-office culture with rapid growth 

 Chapters: 

(00:00) Introduction to Colton Pace – Damon introduces Colton, CEO of OwnWell, and sets up the conversation about managing real estate costs effectively. 

(02:00) Managing Assets to Democratizing Access – Colton shares his journey from managing billionaire assets to founding OwnWell to help everyday homeowners. 

(05:30) Property Taxes: Not as Fixed as You Think – Colton explains how OwnWell helps homeowners challenge and lower their property tax bills. 

(09:00) Building the OwnWell Platform – Colton discusses the technology and team behind OwnWell and the importance of co-founders in scaling a business. 

(12:30) Leadership Lessons from Business School – Colton reflects on the value of his MBA experience and how it shaped his approach to culture and leadership. 

(17:00) Hiring for Culture and Curiosity – Colton shares tips for recruiting team members who align with company values and thrive in collaborative environments. 

(21:30) Advice for Aspiring Founders – Colton offers actionable steps for entrepreneurs to test their ideas, find customers, and scale their businesses efficiently. 

(33:18) The Future of OwnWell – Colton discusses his vision for OwnWell as a digital assistant for real estate owners, providing personalized recommendations and savings 

About Colton: 

Colton Pace is the co-founder and CEO of OwnWell, a venture-backed startup that helps property owners reduce expenses through automated solutions, drawing on his extensive experience managing billions across multiple asset classes. His career spans roles in wealth management, venture capital, and asset management, where he was involved with early investments in notable companies like Uber, Spotify, and Snowflake. After graduating from UCLA's Anderson School of Management, Pace founded OwnWell to democratize access to sophisticated financial tools previously available only to ultra-high-net-worth individuals. Under his leadership, OwnWell has grown to serve over 350,000 customers with more than 100 employees. 

Resources Referenced: 

OwnWell Website 

Colton Pace on LinkedIn 

Podcast Contact Information: 

Website: www.learnit.com 

Email: podcast@learnit.com 

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