What does it really take to build, scale, and lead technology companies that last?

In this episode of Tech Scenes, we go inside Enterprise Rising for a fast-moving conversation with founders, operators, investors, and serial entrepreneurs shaping the future of Midwest tech, enterprise SaaS, sports technology, recruiting, workflow automation, edtech, digital platforms, and startup execution.

Live from Enterprise Rising, this conversation captures the energy of the Midwest startup ecosystem and the builders who are helping move it forward. The episode covers what it takes to find the real constraint in a business, build technology for industries that need it, lead through growth, improve how teams work, and create companies with the discipline to execute.

This episode features: Andre “Dre” Creighton, Dick Polipnick, Doug Berg, Joe Keeley, John Sundberg, Jon Maichel Thomas, Michael Gorman, Scott Burns, and Mark Lacek

Chapters:

00:00 — Opening hook: focus on the real constraint

00:34 — Tech Scenes at Enterprise Rising

01:06 — Andre “Dre” Creighton: finance, operations, and founder perspective

01:15 — Dick Polipnick: GoRout and sports technology adoption

01:21 — Doug Berg: Match2, recruiting, and helping people find the right fit

01:32 — John Sundberg: Kinetic Data and enterprise workflow

01:55 — Jon Maichel Thomas: MadeDaily, UX, design, and secure digital platforms

02:10 — Michael Gorman: Cascade Reading, edtech, and investing

02:24 — Scott Burns: investing, entrepreneurship, and pattern recognition

02:54 — Mark Lacek: serial entrepreneurship and builder perspective

03:30 — Why old industries need better technology

04:28 — Enterprise software, workflow, and solving real customer pain

05:10 — Design, trust, security, and digital product experience

06:01 — Founder finance, constraints, and scaling choices

06:51 — Talent technology, recruiting, and the candidate experience

07:33 — Joe Keeley on coaching, leadership, and the human side of entrepreneurship

08:26 — Building durable products and earning user trust

09:42 — Investor and operator lessons on focus and execution

11:28 — Hard-earned founder lessons from scaling companies

12:25 — AI, recruiting, workflow, edtech, and real-world adoption

13:09 — Coaching, leadership, and company-building

14:05 — Reading technology, education, and thoughtful investing

14:45 — Startup pattern recognition and practical execution

15:53 — Final founder reflections from the room

18:26 — Closing thoughts on execution, conviction, and Midwest momentum

19:19 — Outro

Topics include:

Startup execution

Founder leadership

Enterprise SaaS

Midwest technology companies

Sports technology

Recruiting and talent technology

Workflow automation

Venture investing

Product focus

Leadership alignment

Operating rhythm

Team execution

Scaling growth companies

The Minneapolis, St. Paul, Twin Cities, and Midwest startup ecosystem

At Collective Genius™, we help CEOs build organizations that execute together through the Peak Operating System™ — aligning people, priorities, metrics, and operating rhythms so growth teams can move faster with clarity and focus.

Learn more about the book Peak Teams – Mastering the Habits of Unstoppable Venture-Backed Companies: https://a.co/d/hp5Jtnu

Visit Collective Genius™ to build your growth team with the Peak Operating System™: https://www.collective-genius.com/

Explore Collective Genius™ insights on leadership, execution, scaling teams, operating rhythm, and organizational alignment: https://awesome.collective-genius.com/insights/

Insights Article

Why Growth Companies Need Operating Discipline Before They Scale - https://awesome.collective-genius.com/insights/why-growth-companies-need-operating-discipline-before-they-scale-mrc6dala

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