The Mistakes, Mindsets & Systems Behind Business Growth | Matt Symes

Matt Symes joins Levi and Colby to talk about his evolution from academia and consulting into building a portfolio of businesses and the failures, partnerships, and leadership lessons that shaped the path. They dig into long-term value creation, choosing the right partners, building trust, and why business fundamentals and habit change still matter.The conversation also explores what AI means for entrepreneurs, education, work, and the future of business. Matt shares why an AI strategy should start with a real business constraint, how roles will shift as humans and AI work together, and why understanding how your business actually operates is becoming even more important.Connect with Matt:   https://www.linkedin.com/in/matt-symes-8328a765     Connect with Levi:    https://www.linkedin.com/in/levilawrenceConnect with Colby: https://www.linkedin.com/in/colby-jardine Timestamps:00:00 – Introduction• Levi and Colby introduce Matt Symes and the broader conversation around leadership, business and personal evolution.02:44 – Matt Symes' Background and Evolution• Matt talks about his family history, academia, entrepreneurship and how his own approach has changed over time.05:20 – From Consulting to Building a Business Portfolio• How Simplicity evolved from selling consulting time toward equity investments, Levership and larger transformations.14:55 – Failed Bets and Learning Where You Add Value• Biotech, blue cheese, startups and other failed investments that helped Matt understand where his team could create the most value.20:46 – From Consulting to Long-Term Value Creation• Why traditional consulting relationships frustrated Matt and pushed him toward longer-term partnerships and aligned incentives.29:18 – Choosing the Right Business Partners• What Matt looks for in founders, how he evaluates past failures and why accountability matters when choosing a partner.34:37 – Business Fundamentals, Habits and Scalable Systems• Why knowing what to do is rarely the problem — and how fundamentals, workflows and consistent execution create scalable businesses.40:13 – Building Trust as a Leader• Matt explains the “speed of trust,” the roles of empathy, logic and authenticity, and what he learned about his own leadership weaknesses.54:32 – Academia, Research and the Future of Education• How academic research skills became more useful in an AI-enabled world, followed by a discussion about degrees, mastery and learning.1:12:42 – AI, Job Fear and the Future of Work• Why new technology makes lost jobs easier to see than the new forms of value it may create.1:19:10 – Human Experiences With AI-Enabled Businesses• Why customers may increasingly expect both meaningful human experiences and seamless technology behind them.1:25:38 – Building a Practical AI Roadmap• Matt explains why businesses should start with their goals, identify their biggest constraint and use AI to improve the workflow behind it.1:33:33 – AI Adoption, Custom Software and Falling Behind• Why simply waiting for existing software to add AI may not be enough and how Matt introduces skeptical business owners to AI.1:39:23 – Using AI to Amplify Existing Expertise• Matt and Colby use golf as an example of combining deep existing knowledge with AI to improve performance.1:42:24 – Closing Thoughts• Matt reflects on the conversation, business fundamentals and helping more small businesses adapt.