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PODCAST

In The Trenches

The only podcast dedicated exclusively to Entrepreneurs and CEOs running Small to Medium Sized Businesses (SMB). Nobody knows what it’s like to be an Entrepreneur or CEO unless you’ve been one. Though many understand the rewards of company leadership, very few understand the arduous journey that’s required to get (and stay) there. I share my own lessons as an Entrepreneur and CEO, and interview experts spanning Sales, Leadership, Mental Health, M&A, and Operations (among others) all with a

business entrepreneurship

All Episodes

00:22:57

Migrating Your Software Company from On-Premise to...

In The Trenches ·

2021/06/10

In Part 1 of this Audio Blog, we evaluated some of the more common challenges that companies face when attempting to migrate both their product and revenue models from that of on-premise to SaaS. I guided my own company through this transition over many years. Though we did end up achieving some success, our transition ultimately went too slow, required too much time and capital, and came in below our initial targets. In this Audio Blog (Part 2), I leverage this first-hand experience to walk you

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00:24:11

What I Learned During my First (Failed) Attempt to...

In The Trenches ·

2021/06/04

As CEOs, many of youare undoubtedly considering the possibility of selling your business at some point in the future. In 2018, I attempted to sell my own business, though was unsuccessful in doing so. From start to finish, the sale process took upwards of 12 grueling months. Hundreds of potential suitors were narrowed down to a dozen or so, which in turn were narrowed down to a single acquiror with whom we completed the extensive financial, legal, technical, and commercial due diligence

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00:21:14

Considerations in Selecting Your M&A Advisor

In The Trenches ·

2021/06/02

As CEOs & Entrepreneurs, I suspect many of you have at least considered the possibility of an exit, whether it be in the near or long-term future. In my experience selling my own business, the selection of my M&A Advisor was perhaps one of the most important decisions that I had to make, and in retrospect so many other decisions (and their outcomes) flowed directly from this one critical choice. I once chose a bad advisor, and have since worked with a great one. Based on these experiences, I

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00:17:13

Pricing Power: How Small Changes Can Have Big Impacts

In The Trenches ·

2021/05/30

As CEOs & Entrepreneurs, we all know that there are a countless number of levers that one can pull to grow revenue or profitability, all of which will have varying degrees of impact. Increasing prices is one such lever, however it is somewhat unique. In this audio blog, I explain why. I argue that in certain circumstances, raising the prices that you charge to existing customers is one of the fastest, most effective, and “lowest friction” ways to unlock a nascent revenue and profitability

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01:28:32

The Private Equity Perspective on Acquiring,...

In The Trenches ·

2021/05/27

My guest today is Jordan Bettman. Jordan is a Partner and Co-founder of Radian Capital, a New York-based Private Equity firm focused on B2B software and technology-enabled services businesses. Radian currently has ~$500 million of assets under management, and is now investing out of their second fund. Prior to co-founding Radian, Jordan was a Partner at Bain Capital Ventures for nearly a decade, where he focused largely on financial services and back-office technology investments. He currently

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00:24:04

Migrating Your Software Company from On-Premise to...

In The Trenches ·

2021/05/26

Today’s audio blog is specific to software, and concerns the migration from i) a business model characterized by on-premise hosting and one-time perpetual-use licensing fees, to ii) a new business model characterized by cloud-based hosting and a subscription licensing. This process is generally referred to as the "On-Premise to SaaS Migration". Most software companies founded over the past fifteen years or so have never known anything other than the latter model, however, for anybody running a

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00:20:50

Hiring Your Senior Leadership Team

In The Trenches ·

2021/05/17

In my experience as a CEO, I came to learn that surrounding myself with A+ people (particularly at the senior leadership team level) was one of the most impactful things that I could do for both myself and my company. Even if you are above average with respect to your ability to hire great people (most people think that they are – yet most people are not), it is a virtual guarantee that you'll make some mistakes as you build out your leadership team. I certainly did. It took me many years (and many

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00:22:20

Why So Many Companies Rarely Achieve Their Annual Goals

In The Trenches ·

2021/05/17

Today’s episode is all about execution, and more specifically what you need to do to give yourself the best odds of actually executing on the goals that you set for your organization. There’s a well-known maxim that you might be familiar with that states “Strategy without execution is hallucination”, and in today’s audio blog I’ll share with you why I think that’s true. I’ll do so by sharing some of the lessons that I’ve learned over the years related to executing on the strategy you set. In my

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00:16:36

The Entrepreneur and Mental Health (Part 2): My...

In The Trenches ·

2021/05/13

In today's post, I share with you the lessons I’ve learned to deal with (or prevent, as much as possible) the mental health toll that entrepreneurship (or leadership, or success) can take: Of course, these lessons are only now clear to me with the benefit of hindsight vision being of the 20/20 variety. When you’re constantly in the trenches, like so many Entrepreneurs and CEOs are, it’s difficult to see the forest from the trees. For this reason, I hope you’ll find this Audio Blog to be highly

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00:19:46

The Entrepreneur and Mental Health (Part 1): My Journey

In The Trenches ·

2021/05/13

In this Audio Blog, I provide you with a brief summary of my own mental health journey as a leader. My goal isn’t to provide you with an exhaustive account of my journey, but rather to simply discuss it publicly. After all, if I don’t do my own part to contribute to the discussion around the worries, thoughts, and fears that Entrepreneurs and CEOs face, what right do I have to lament that it isn’t being discussed enough more broadly? This will be my only Audio Blog solely about me. Though it may be

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01:29:57

Sales: Hiring, Onboarding, Compensating, Scaling &...

In The Trenches ·

2021/04/29

In this episode I interview Dave Prusinksi, currently the Chief Revenue Officer at SafeAI, a hyper-growth silicon valley company in the autonomous vehicle space. Here is why I think Dave is a person worth listening to: Prior to his current role, Dave spent 10 years as the Executive Vice President of Sales and Marketing at FleetComplete, a technology provider to fleet-owning businesses around the world. Under Dave's leadership, FleetComplete grew from $6M ARR to $150M in total revenue, achieving an

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00:00:59

In The Trenches (Trailer)

In The Trenches ·

2021/04/19

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