The Small Business Black Holes with Alan Pentz
Welcome to The Small Business Black Holes podcast show with Alan Pentz, where we help you navigate the chaos of today's world with precision. Forget the old playbook - it's toast. We’re in a new game now, and Alan Pentz is here to help you win.
Alan brings 25 years of experience working at the highest levels of business and government, from Capitol Hill to advising the federal government on cutting-edge innovation. He’s seen the old rules fall apart and knows what it takes to thrive in this brave new world.
Whether it's superpowers battling for dominance or inflation throwing everyone for a loop, Alan helps you play 4D chess while everyone else is stuck on checkers? Let’s dive in.
- Update frequency
- every 7 days
- Average duration
- 40 minutes
- Episodes
- 87
- Years Active
- 2024 - 2025
Re-Released: Prof. Matt Green on Why Congress Feels More Divided Than Ever
As part of our re-release series, we are revisiting an important episode of Small Business Black Holes featuring Professor Matthew Green, a political science scholar at Catholic University and an exp…
00:42:08 |
Tue 02 Sep 2025
Stop Hiring Sales Teams Too Early: The Hidden $250K Mistake Most Owners Make
In this episode of SBP - Small Business Bootstrapped, Alan deconstructs the economic realities behind this critical growth inflection point and reveals how emerging AI technologies are creating unpre…
00:44:07 |
Tue 26 Aug 2025
The Death of Mediocrity: How AI is Forcing Small Business Evolution | Steven Wilkinson
This intellectually rich episode of Small Business Black Holes examines the fundamental forces reshaping entrepreneurial success in the AI era. Host Alan Pentz engages with Steven Wilkinson—a seasone…
00:41:09 |
Tue 19 Aug 2025
Why Everyone's Becoming an AI Operator – Insights from Tim Cakir
The convergence of natural language processing and automated reasoning is fundamentally reshaping business operations, transitioning from deterministic workflows to adaptive, multi-tool agent systems…
00:41:32 |
Tue 12 Aug 2025
Work 45 Hours, Grow 4 Hours: The Small Business Time Trap
Small business leaders face a critical paradox: intensified work schedules yielding diminished strategic output. In this analytical discussion, host Alan Pentz and Chad Brooks, Senior Managing Editor…
00:24:06 |
Tue 05 Aug 2025
The AI Gamble: How Losing 50% of Clients Made Charlie Felker Millions
What separates visionary entrepreneurs from those left behind isn't just their willingness to embrace new technology—it's their ability to recognize inflection points and act decisively when others h…
00:26:22 |
Tue 29 Jul 2025
The Dark Knowledge Crisis with Luca Rossetti
AI is rapidly transforming how businesses operate, yet many organizations remain unprepared for the seismic shifts ahead in knowledge management and automation.
In this episode of Small Business Black…
00:35:01 |
Tue 22 Jul 2025
Flying Backwards: The Case for Real-Time Business Intelligence
In this episode of Small Business Black Holes, Elizabeth Gore, co-founder of Hello Alice, reveals why even Michael Dell loses sleep over cash flow and how her platform serves 1.5 million entrepreneur…
00:25:38 |
Tue 15 Jul 2025
The Zone of Genius: Why Business Owners Are Abandoning Their Greatest Advantage
The greatest tragedy in modern entrepreneurship isn't failure—it's the systematic abandonment of authentic competitive advantage in favor of imitation and external validation.
In this intellectually p…
00:19:33 |
Tue 08 Jul 2025
The Hidden Gold Mine in SMB Tech: NetSurit's Blueprint for 10X Growth Without PE Backing
AI and automation are revolutionizing how small and medium-sized businesses operate, making enterprise-grade solutions accessible and affordable at unprecedented levels.
In this episode of Small Busin…
00:38:57 |
Tue 01 Jul 2025
Breaking Free from the $1M Revenue Trap: Why Most Owners Stay Stuck
Breaking Free from Business Black Holes: Understanding Owner Involvement and Growth Barriers
In this episode of Small Business Black Holes, host Alan and co-host Tonya explore insights from a business…
In this episode of Small Business Black Holes, host Alan and co-host Tonya explore insights from a business…
00:21:23 |
Tue 24 Jun 2025
From Bottleneck to Breakthrough: How Top 4% of Owners Scale Past $10M Revenue | Patrick Metzger
In this episode of Small Business Black Holes, host Alan speaks with Patrick Metzger of Growing For Success, a business coach and valuation expert, about helping business owners overcome growth barri…
00:29:26 |
Tue 17 Jun 2025
Duolingo for Business: How OwnerRx is Making Elite Coaching Accessible to All
A groundbreaking AI-powered business coaching platform aims to democratize access to strategic business guidance and make expert consulting accessible to small business owners.
In this episode, Alan P…
In this episode, Alan P…
00:23:53 |
Tue 10 Jun 2025
The Hidden Power of Cold Calling: 11M Calls That Generated $10M+ Revenue | Gabe Lullo, Alleyoop
In this episode of Small Business Black Holes, host Alan speaks with Gabe Lullo, founder of Alleyoop, about revolutionizing B2B sales development through a unique blend of human expertise and technol…
00:39:42 |
Tue 03 Jun 2025
Breaking the Revenue Ceiling: Why Management Training is Your Hidden Growth Lever
In this episode of Small Business Black Holes, host Alan Pentz speaks with Gavin Howarth, CEO of Howarths, a UK-based HR consulting firm. Their discussion covers the delicate process of family busine…
00:38:16 |
Tue 27 May 2025
Agency Alchemy: How Eli Ruble Turned Service Businesses into 67% Profit Machines
From Zero to Millions: A Masterclass in Building Highly Profitable Agencies
In this episode of Small Business Black Holes, host Alan Pentz speaks with Eli Rubel, founder of Profit Labs and serial agen…
00:35:57 |
Tue 20 May 2025
Forget Being Better—Why Differentiation Drives 5X Higher Margins in B2B Marketing
In this episode of Small Business Black Holes, host Alan Pentz speaks with Garrett Mehrguth, founder of Directive and Abe, who scaled his marketing agency to $25M in revenue. They explore how to brea…
00:38:11 |
Tue 13 May 2025
Monthly Check-ins Beat Quarterly Marathons: The Math Works
In this episode of Small Business Black Holes, host Alan and co-host Tonya discuss how traditional business planning sessions can be condensed and optimized using modern tools like AI, making strateg…
00:17:23 |
Tue 06 May 2025
Forget Passion: Why Boring Businesses Create More Millionaires | Nick Huber of Bolt Storage
In this episode of Small Business Black Holes, host Alan Pentz talks with Nick Huber, entrepreneur and author of "The Sweaty Startup," about building sustainable businesses through traditional indust…
00:43:14 |
Tue 29 Apr 2025
From Life Support to Long-Term Success: The Small Business Financial Journey with Simple Numbers
In this episode of Small Business Black Holes podcast, host Alan Pentz sits down with Mike Maxson and Brandon Gray from Simple Numbers, a renowned financial advisory firm, to explore how businesses e…
00:39:03 |
Tue 22 Apr 2025
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