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In The Trenches
Steve Divitkos
126 episodes
5 days ago
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 single goal: To improve the personal and professional lives of Entrepreneurs and CEOs running SMBs.
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Entrepreneurship
Business
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All content for In The Trenches is the property of Steve Divitkos and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
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 single goal: To improve the personal and professional lives of Entrepreneurs and CEOs running SMBs.
Show more...
Entrepreneurship
Business
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Technical Debt: What it is, How Much of it You Can Live With, and How to Incorporate it into an Investment Thesis
In The Trenches
1 hour 26 minutes 21 seconds
1 week ago
Technical Debt: What it is, How Much of it You Can Live With, and How to Incorporate it into an Investment Thesis

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

 

 

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This episode is brought to you by ⁠⁠⁠B⁠⁠⁠⁠⁠⁠⁠⁠oulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠



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Chris Smith is the Managing Partner of Spellbound Partners, a a company that helps acquirors with technical due diligence, fractional CTO services, and outsourced development services, among other things. Chris has over 25 years of experience building software platforms, and is an expert in cloud computing and software as a service (SaaS). He has been a part of numerous founding startup teams and has led multiple teams through high-growth transitions.


Much of what we discuss today is intended to uncover how much “technical debt” any given target company may possess within its code base. Though substantially every software company has some amount of technical debt, those that are weighed down by an asymmetric burden of it tend to experience very real business problems that non-technical acquirors and CEOs may not fully appreciate.


As a result, prospective acquirors would be well served to thoroughly diligence the amount of technical debt possessed by any given target company, and proceed very carefully (or perhaps not proceed at all) with those companies who seem to possess much more than their fair share of it.

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 single goal: To improve the personal and professional lives of Entrepreneurs and CEOs running SMBs.