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Steve Divitkos
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M&A Launchpad
Ups & Downs of the CEO Life with Steve Divitkos
In this episode of the M&A Launchpad Podcast, hosts Feras Moussa and Casey Minshew welcome special guest Steve Divitkos, discussing the challenges of launching and growing a search fund. Steve shares his experiences as a first-time CEO, the emotional toll, strategic decisions, and the eventual exit from his company. Steve dives deep into what it’s like to be a CEO. For example, the challenges he faced around the perception of young CEOs, as well as the decision process between firing and hiring top talent. At the end of the day, Steve states that the path to growth is no...
2024-11-14
37 min
In The Trenches
Dr. Bill Hudenko: Professor of Psychology at the Dartmouth School of Medicine and a 4x Founder & CEO
This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses * 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 * Today I'm joined by Dr. Bill Hudenko, an Assistant Professor of Clinical Psychology at the Dartmouth School of Medicine. In addition to his experience as a professor and clinician, Dr. Hudenko is also a 4x CEO & Entrepreneur, having founded and sold several companies that have utilized technology to improve mental health outcomes for customers. Because of his incredibly unique career that spans coding, entrepreneurship, psychology, medicine, leadership, and technology,
2024-08-15
1h 12
In The Trenches
From Combat to Classrooms: How Jim Vesterman Went from Special Forces to a 13.5x Return in 8 Years
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 * This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses * My guest today is Jim Vesterman, currently a lecturer at the Wharton School at the University of Pennsylvania. Prior to joining the faculty at Wharton, Jim was the CEO of Raptor Technologies, a company that he purchased through his own search fund in 2012, and ran through to a successful exit in 2020. Under Jim’s tenure, Raptor technologies grew from serving 7,000 schools in the United States to serving over 40,000 schools with an in...
2024-08-01
1h 26
In The Trenches
17 Lessons on the Psychology of Being a Searcher and CEO
This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses * 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 * During my ~10 years as a searcher and CEO, I had an endless number of commercial problems and opportunities that required my attention at any given time. However, it was often the personal considerations that kept me up at night: I rarely lost sleep over whether to raise prices by 5% or 15%, but instead was kept awake by the idea that even asking the question suggested that I didn’t truly know what I was doing. I wasn’t...
2024-07-18
31 min
In The Trenches
You Don't Have an Engineering Problem, You Have a Product Management Problem
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 * This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses * Based on my own experience as a software CEO, I think that Product Management is one of the most important - and one of the lest well understood - ingredients to building a successful software company. Many software businesses (particularly mature ones still led by their original Founders) don't have any product management function at all. While this may be tenable under the Founder's leadership, it is almost never tenable when the company...
2024-07-04
1h 06
In The Trenches
Evaluating The Most Common Forms of Debt Used to Finance Small Business Acquisitions
This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses * 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 * Though it is correct to suggest that all acquisitions are funded through some combination of cash-on-hand, debt, or equity, it’s also a bit of an oversimplification. Indeed, the financing options available to prospective acquirors are numerous, and in today’s blog post, I focus specifically on debt, and evaluate the four most common sources of leverage used to finance the purchase of small and medium-sized businesses. These include ban
2024-06-20
27 min
In The Trenches
From $7M to $50M via 14 Acquisitions: A Consolidation Success Story With Jay Davis & Jason Pananos
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 * This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses * I recently published a blog post, Why You May Want to Reconsider Your Industry Roll-up Strategy, within which I detailed many of the ways in which consolidation strategies can go wrong. In today’s episode, I want to look at the opposite side of that coin and dig deeply into an instance where a consolidation strategy went very right. I'm joined today by Jay Davis & Jason Pananos, who, after...
2024-06-06
1h 26
In The Trenches
Why You May Be Ignoring Brokered Deals at Your Peril
This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses * 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 * Today’s episode is all about participating in brokered transactions, and working with brokers more broadly (by "brokers", I am referring to investment banks, accounting firms, business brokers, or any other sell-side advisor whose job it is to help clients sell their companies). To inform our discussion today, I’m joined by Ryan Farkas, a Partner, Managing Director and the Practice Leader in M&A and Capital Markets at BDO, who has successfully closed countle
2024-05-23
1h 06
In The Trenches
Why You May Want to Reconsider Your Industry Roll-up Strategy
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 * This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses * Though pursuing the consolidation of an industry is not necessarily a new thesis within the search fund ecosystem, I have observed that it has become increasingly popular over the past few years among prospective searchers. Though there have been, and will continue to be, many consolidation success stories within the search fund ecosystem, I suspect there will be an equal number of failures, though this latter outcome will surely be much less publicized. Though...
2024-05-09
19 min
In The Trenches
45 (More) Things That I Think Are True
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 * This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses * In a previous post (75 Things That I Think Are True), I compiled quotes from countless books, mentors, podcasts and blogs to present 75 ideas that I believed to be fundamentally true, spanning both business and personal considerations. Since publishing that post last year, I have come across 45 additional quotes that I thought were also worthy of presentation. I hope that some of these new submissions also distill a lifetime of wisdom into o
2024-04-25
11 min
In The Trenches
The Constellation Software Playbook for Acquiring and Growing Software Companies
This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses * 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 * Constellation Software is one of the world's most widely followed and admired software companies, having acquired upwards of 500 lower-middle-market software companies since its founding in 1995. Our guest today, Mike Dufton, is the CEO of the Volaris group, one of the six major operating units within Constell
2024-04-11
1h 17
In The Trenches
Evaluating Stock Options as Attraction, Retention, and Incentive Alignment Tools
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 * This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses * After many years of using company stock options as attraction, retention, and incentive alignment tools, I’ve come to appreciate their merits, risks, and possible alternatives. I intend to share these lessons with you today. More specifically though, I will argue that w...
2024-03-28
22 min
In The Trenches
Can Ambition and Inner Peace Coexist? With Rob Dube
This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses * 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 * Today I'm joined by entrepreneur, CEO, and best-selling author, Rob Dube. In 1991, Rob co-founded imageOne, a managed print services business based in Oak Park, Michigan, that has won countless awards across countless publications for it’s growth, culture, and employee engagement...
2024-03-14
1h 26
In The Trenches
Answers to Recurring FAQs from Current and Prospective Searchers
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 * This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses * Many searchers understandably tend to have very similar questions and areas of uncertainty. Indeed, in most instances, I had these very same questions and areas of uncertainty myself prior to raising my own search fund in 2012. As a result of the frequency with which I'm asked...
2024-02-29
44 min
In The Trenches
Profit Before Anything Else: With Mike Michalowicz, Author of "Profit First"
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 * This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses * Today I'm joined by Entrepreneur, Investor, and Author Mike Michalowicz. In addition to being the author of 9 books, Mike is himself a serial entrepreneur, having founded, operated, and successfully exited several companies across his multi-decade career. He now spends much of his professional time writing, speaking, and coaching CEOs and entrepreneurs on the various systems that helped ma...
2024-02-14
1h 19
In The Trenches
Royce Yudkoff & Rick Ruback: Educators, Mentors, and Leaders Within the SMB Community
This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses * 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 * Today I am thrilled to be joined by two guests that, without the risk of hyperbole, have changed my life in more ways than I can count. Royce Yudkoff & Rick Ruback are both professors at the Harvard business school, and co-teach two wildly popular courses called “The Financial Management of Smaller Firms” and “Entrepreneurship through Acquisition”, both of wh...
2024-02-01
1h 02
In The Trenches
Jeff Stevens & A.J. Wasserstein on The Future of Entrepreneurship Through Acquisition
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 * This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses * Today I'm joined by two of the most thoughtful, distinguished, and respected investors in the ETA ecosystem, Jeff Stevens and A.J. Wasserstein, to discuss the future of acquisition entrepreneurship. The paper that inspired this episode, written by both Jeff & A.J...
2024-01-18
1h 32
In The Trenches
Michael Girdley on The Rise of Holding Companies
This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses * 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 * Today I'm joined by Michael Girdley, an entrepreneur and investor who has spent the past 30 years building a personal holding company boasting over $100M in annual revenue, comprised of 12 businesses across software, technology, consumer re...
2024-01-04
57 min
In The Trenches
Questions You Should Be Prepared to Answer Before Buying (or Selling) a Small Business
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 * This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses * Over many years of evaluating acquisition targets alongside searchers, I’ve found that certain questions tend to apply more often than not. I’ve presented each of these FAQs in today's episode, in hopes that they play a small r...
2023-12-21
29 min
In The Trenches
What I'd Change if I Could Re-Do the First 90 Days of my Search: 3 Searcher Case Studies
This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses * 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 * In today's episode, I will be speaking with 3 searchers, each of whom are at different stages of their respective search journeys. As I have done in the past, I will again be asking these guests only a single question: Knowing what...
2023-12-07
1h 00
In The Trenches
Dr. Victoria Medvec on the Art and Science of High Stakes Negotiations
This episode is brought to you by Symphony. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. Just go to the Contact form on their website and tell them that you’re a listener of the podcast to receive this discount! * This episode is brought to you by Oberle Risk Strategies, the leading insurance broker...
2023-11-23
1h 35
In The Trenches
Peter Lehrman, Founder & CEO of Axial, The Largest Online Marketplace to Buy & Sell SMBs
This episode is brought to you by Oberle Risk Strategies, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by August Felker (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company’s insurance program, including any potential coverage gaps, the pro-forma insurance pricing, and the program structure changes needed for closing. At or shortly after closing, they then execute on all of those findings on your behalf. Oberle has serviced over 900 customers across a decade of...
2023-11-09
1h 24
In The Trenches
Conscious Leadership with Executive Coach and Best-Selling Author Kaley Klemp
This episode is brought to you by Symphony. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. Just go to the Contact form on their website and tell them that you’re a listener of the podcast to receive this discount! * This episode is brought to you by Oberle Risk Strategies...
2023-10-26
57 min
In The Trenches
Building a $5.5B Mid-Market Private Equity Firm: Brent Belzberg, Founder of Torquest Partners
This episode is brought to you by Oberle Risk Strategies, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by August Felker (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company’s insurance program, including any potential coverage gaps, the pro-forma insurance pricing, and the program structure changes needed for closing. At or shortly after closing, they then execute on all of those findings on your behalf. Oberle has serviced over 900 customers across a d...
2023-10-12
1h 16
In The Trenches
My Experience With Anxiety
This episode is brought to you by Symphony. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. Just go to the Contact form on their website and tell them that you’re a listener of the podcast to receive this discount! * This episode is brought to you by Oberle Risk Strategies, the leading insu...
2023-09-28
24 min
In The Trenches
A Deep Dive on Compensation
This episode is brought to you by Oberle Risk Strategies, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by August Felker (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company’s insurance program, including any potential coverage gaps, the pro-forma insurance pricing, and the program structure changes needed for closing. At or shortly after closing, they then execute on all of those findings on your behalf. Oberle has serviced over 900 cust...
2023-09-14
1h 07
In The Trenches
A Deep Dive on Hiring
This episode is brought to you by Symphony. On September 8th, 2023, Symphony will be live-streaming a webinar on searchfunder.com all about the technical due diligence process when acquiring a software company. Use this link to sign up: https://www.searchfunder.com/event/view/1200. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenc...
2023-08-31
2h 17
In The Trenches
"A Guide to the Good Life": What Entrepreneurs Can Learn From Stoic Philosophy
This episode is brought to you by Oberle Risk Strategies, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by August Felker (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company’s insurance program, including any potential coverage gaps, the pro-forma insurance pricing, and the program structure changes needed for closing. At or shortly after closing, they then execute on all of those findings on your behalf. Oberle has serviced over...
2023-08-17
1h 19
In The Trenches
Venture Capital “Orphans”: Exploring an Emerging Search Fund Investment Thesis
This episode is brought to you by Symphony. On September 8th, 2023, Symphony will be live-streaming a webinar on searchfunder.com all about the technical due diligence process when acquiring a software company. Use this link to sign up: https://www.searchfunder.com/event/view/1200. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In t...
2023-08-03
17 min
In The Trenches
When Search Funds Don’t Go As Planned (Part 2): With Jim Sharpe
This episode is brought to you by Symphony. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. Just go to the Contact form on their website and tell them that you’re a listener of the podcast to receive this discount! * This episode is brought to you by Oberle Risk Strategies, the leading insurance brokera...
2023-07-22
1h 02
In The Trenches
Lessons Learned From 400+ Post-Exit Entrepreneurs: John Warrillow, Host of Built to Sell Radio
This episode is brought to you by Oberle Risk Strategies, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by August Felker (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company’s insurance program, including any potential coverage gaps, the pro-forma insurance pricing, and the program structure changes needed for closing. At or shortly after closing, they then execute on all of those findings on your behalf. Oberle has se...
2023-07-22
53 min
In The Trenches
When Search Funds Don't Go As Planned (Part 1): 3 Searcher Case Studies
This episode is brought to you by Oberle Risk Strategies, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by August Felker (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company’s insurance program, including any potential coverage gaps, the pro-forma insurance pricing, and the program structure changes needed for closing. At or shortly after closing, they then execute on all of those findings on your behalf. Oberle...
2023-06-22
1h 54
In The Trenches
75 Things That I Think Are True
This episode is brought to you by Symphony. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. Just go to the Contact form on their website and tell them that you’re a listener of the podcast to receive this discount! * This episode is brought to you by Oberle Risk Strategies, the lead...
2023-06-08
22 min
In The Trenches
The SMB Credit Markets: Bank Failures, Rising Interest Rates, and a Looming Recession
This episode is brought to you by Oberle Risk Strategies, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by August Felker (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company’s insurance program, including any potential coverage gaps, the pro-forma insurance pricing, and the program structure changes needed for closing. At or shortly after closing, they then execute on all of those fin...
2023-05-25
1h 09
In The Trenches
The Merits, Risks, and Possible Unintended Consequences of Earn-Outs
This episode is brought to you by Symphony. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. Just go to the Contact form on their website and tell them that you’re a listener of the podcast to receive this discount! * Thi...
2023-05-11
23 min
In The Trenches
Mental Health for High Achievers: Ambition, Anxiety, Perfectionism, and Balancing Striving vs. Self-Acceptance
This episode is brought to you by Symphony. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for listeners of In the Trenches. Just go to the Contact form on their website and tell them that you’re a listener of the podcast to receive this discount! *
2023-04-27
1h 34
In The Trenches
The 2023 SaaS CEO Survey
This episode is brought to you by Avidbank. Avidbank is one of the most experienced search fund lenders in North America, having funded over 40 separate transactions since 2014, for a total of over $300M. They are deeply familiar with the search fund model, and understand the nuances of the fundraising process, dealing with sellers, communicating with your equity investors, LOI reviews, and everything else in between. Reach out to Anthony Rodriguez (arodriguez@avidbank.com) or Conor Tidgwell (ctidgwell@avidbank.com) to learn more. * This episode is brought to you by Symphony. Symphony not only performs technical due dili...
2023-04-13
34 min
In The Trenches
Kent Weaver: Building, Working With, and Learning from your Board of Directors
This episode is brought to you by The Profit Line. The Profit Line is a boutique finance and accounting firm that provides a wide range of accounting services to small and medium businesses generating anywhere between $5M to $50M in revenue. On a fractional, outsourced basis, they do day-to-day bookkeeping, bank reconciliations, month-end accruals, tax compliance, and financial statement preparation, among countless other things. I was a customer of theirs for 7 consecutive years while running my own company, and am speaking as a happy customer. Book a call with Founder and CEO, Fern Gordon (Ferngordon@theprofitline.com) or visit th...
2023-03-29
55 min
In The Trenches
How to Know When it's Time to Stop
It's not hard to understand the importance of persistence to the entrepreneurial journey. Entrepreneurs who overcome substantial hardships on their eventual road to success are (rightly) applauded for the otherworldly persistence that they demonstrated in doing so. Yet many entrepreneurs are able to finally achieve success only after moving on from several prior ventures whose prospects eventually grew to become much less promising. These entrepreneurs are also (rightly) applauded, though this time it’s for the foresight, objectivity and courage that they demonstrated in making what must have been an incredibly difficult decision to “quit”. So, which is it? Should entrepre...
2023-03-22
17 min
In The Trenches
Are You Selling to the Wrong Customers?
This episode is brought to you by Avidbank. Avidbank is one of the most experienced search fund lenders in North America, having funded over 40 separate transactions since 2014, for a total of over $300M. They are deeply familiar with the search fund model, and understand the nuances of the fundraising process, dealing with sellers, communicating with your equity investors, LOI reviews, and everything else in between. Reach out to Anthony Rodriguez (arodriguez@avidbank.com) or Conor Tidgwell (ctidgwell@avidbank.com) to learn more. * This episode is brought to you by The Profit Line. The Profit Line i...
2023-03-16
28 min
In The Trenches
Everything You've Ever Wanted to Know About Working with a Partner: With Dr. Noam Wasserman, Author of The Founder's Dilemmas
This episode is brought to you by The Profit Line. The Profit Line is a boutique finance and accounting firm that provides a wide range of accounting services to small and medium businesses generating anywhere between $5M to $50M in revenue. On a fractional, outsourced basis, they do day-to-day bookkeeping, bank reconciliations, month-end accruals, tax compliance, and financial statement preparation, among countless other things. I was a customer of theirs for 7 consecutive years while running my own company, and am speaking as a happy customer. Book a call with Founder and CEO, Fern Gordon (Ferngordon@theprofitline.com) or visit th...
2023-03-02
1h 37
In The Trenches
Evaluating the Correlation Between Hours Worked and Success Achieved
This episode is brought to you by The Profit Line. The Profit Line is a boutique finance and accounting firm that provides a wide range of accounting services to small and medium businesses generating anywhere between $5M to $50M in revenue. On a fractional, outsourced basis, they do day-to-day bookkeeping, bank reconciliations, month-end accruals, tax compliance, and financial statement preparation, among countless other things. I was a customer of theirs for 7 consecutive years while running my own company, and am speaking as a happy customer. Book a call with Founder and CEO, Fern Gordon (Ferngordon@theprofitline.com) or visit th...
2023-02-16
14 min
In The Trenches
The Smallest Changes That Had The Largest Impacts: 4 CEO Case Studies
This episode is brought to you by The Profit Line. The Profit Line is a boutique finance and accounting firm that provides a wide range of accounting services to small and medium businesses generating anywhere between $5M to $50M in revenue. On a fractional, outsourced basis, they do day-to-day bookkeeping, bank reconciliations, month-end accruals, tax compliance, and financial statement preparation, among countless other things. I was a customer of theirs for 7 consecutive years while running my own company, and am speaking as a happy customer. Book a call with Founder and CEO, Fern Gordon (Ferngordon@theprofitline.com) or visit th...
2023-02-02
1h 30
In The Trenches
Constructing, Managing, and Working with a Board of Directors
This episode is brought to you by Warren Coughlin, CEO Coach and founder of JumpStart Coaching. Warren focuses exclusively on coaching CEOs running SMBs, and has been doing so for over 20 years. One of my biggest regrets across my 7 years as a CEO was not hiring a coach, and I want to prevent others from making the same mistake. For listeners of In The Trenches, working with Warren is effectively risk-free: If at the end of the first three months you're not happy with the direction of your business, he will give you your money back. On top of...
2023-01-19
21 min
In The Trenches
Mike Zani, CEO of The Predictive Index: Hiring, Personality Profiling Tools, Working with a Partner, and Other Lessons from 20 Years as a CEO
This episode is brought to you by Warren Coughlin, CEO Coach and founder of JumpStart Coaching. Warren focuses exclusively on coaching CEOs running SMBs, and has been doing so for over 20 years. One of my biggest regrets across my 7 years as a CEO was not hiring a coach, and I want to prevent others from making the same mistake. For listeners of In The Trenches, working with Warren is effectively risk-free: If at the end of the first three months you're not happy with the direction of your business, he will give you your money back. On top of...
2023-01-05
1h 30
In The Trenches
The Current State of the Debt Capital Markets
This episode is brought to you by Warren Coughlin, CEO Coach and founder of JumpStart Coaching. Warren focuses exclusively on coaching CEOs running SMBs, and has been doing so for over 20 years. One of my biggest regrets across my 7 years as a CEO was not hiring a coach, and to the best extent possible, I want to prevent others from making the same mistake. For listeners of In The Trenches, working with Warren is effectively risk-free: If at the end of the first three months you're not happy with the direction of your business, he will give you your...
2022-12-22
59 min
In The Trenches
Evaluating 5 Very Different Approaches to Acquiring a Software Company
This episode is brought to you by Warren Coughlin, CEO Coach and founder of JumpStart Coaching. Warren focuses exclusively on coaching CEOs running SMBs, and has been doing so for over 20 years. One of my biggest regrets across my 7 years as a CEO was not hiring a coach, and to the best extent possible, I want to prevent others from making the same mistake. For listeners of In The Trenches, working with Warren is effectively risk-free: If at the end of the first three months you're not happy with the direction of your business, he will give you your...
2022-12-08
30 min
In The Trenches
Brent Beshore: The "Forrest Gump of Private Equity"
This episode is brought to you by Cayne Crossing. Cayne Crossing helps prospective SMB purchasers with all aspects of financial due diligence, including producing the Quality of Earnings report. I have personally read though, analyzed, and relied upon several of their actual QofE reports in my capacity as an SMB investor, and can personally attest to the quality of the work that they do. Unlike any other QofE provider that I’m aware of, Cayne Crossing also co-invests alongside their buyers, aligning their interests with yours in a way that I simply haven’t seen anywhere else. Cayn...
2022-11-24
1h 27
In The Trenches
Tools in Managing my own Psychology
This episode is brought to you by Cayne Crossing. Cayne Crossing helps prospective SMB purchasers with all aspects of financial due diligence, including producing the Quality of Earnings report. I have personally read though, analyzed, and relied upon several of their actual QofE reports in my capacity as an SMB investor, and can personally attest to the quality of the work that they do. Unlike any other QofE provider that I’m aware of, Cayne Crossing also co-invests alongside their buyers, aligning their interests with yours in a way that I simply haven’t seen anywhere else. Cayn...
2022-11-10
22 min
In The Trenches
A.J. Wasserstein: Reflections of a Founder, CEO, Investor and Educator
This episode is brought to you by Cayne Crossing. Cayne Crossing helps prospective SMB purchasers with all aspects of financial due diligence, including producing the Quality of Earnings report. I have personally read though, analyzed, and relied upon several of their actual QofE reports in my capacity as an SMB investor, and can personally attest to the quality of the work that they do. Unlike any other QofE provider that I’m aware of, Cayne Crossing also co-invests alongside their buyers, aligning their interests with yours in a way that I simply haven’t seen anywhere else. Cayn...
2022-10-27
1h 13
In The Trenches
The CEO as Chief Capital Allocator
This episode is brought to you by Cayne Crossing. Cayne Crossing helps prospective SMB purchasers with all aspects of financial due diligence, including producing the Quality of Earnings report. I have personally read though, analyzed, and relied upon several of their actual QofE reports in my capacity as an SMB investor, and can personally attest to the quality of the work that they do. Unlike any other QofE provider that I’m aware of, Cayne Crossing also co-invests alongside their buyers, aligning their interests with yours in a way that I simply haven’t seen anywhere else. Cayne...
2022-10-13
20 min
In The Trenches
Buy at 5X EBITDA, Sell at 8X Revenue: The On-Premise to SaaS Transition of FieldEdge
My guests today are Steve Lau and Rameez Ansari, co-CEOs of AutoLeap, a software company that services auto repair shops, that counts Bain Capital Ventures among its investors. Prior to founding AutoLeap, Steve and Rameez purchased, operated, and sold D'Esco (later renamed FieldEdge), a software company that helps entrepreneurs run their HVAC, Plumbing, and Electrical Contracting businesses. Steve and Rameez purchased the company from its original founder in 2015 at 5X EBITDA, when its product was entirely on-premise and its revenue was generated solely through the sale of perpetual use licenses. After successfully transitioning the...
2022-09-29
1h 18
In The Trenches
Knowing Who, When, and How to Fire
Unfortunate at this reality may be, I would argue that firing (specifically knowing who, when, and how to fire) is a required core competency for any CEO, and is arguably as important as hiring, communication, capital allocation, and other tools within the CEO’s toolkit. The extent to which this is an unpleasant (and perhaps even unpopular) topic to discuss doesn’t negate its critical importance in building and sustaining a healthy and vibrant company. Some may associate the idea of firing with toxic, authoritarian, or fear-based work cultures. While firing can lead to these types of outcomes if done in a...
2022-09-15
19 min
In The Trenches
Sell-Side M&A Advisors: How to Choose One, How Much They Cost, and The Importance of the "Fine Print"
Today’s episode is for anybody who ever plans to sell a company. Most entrepreneurs will sell a business once in their entire careers (if they’re lucky), and as a result many understandably don’t have a lot of context or experience in the finer points of exiting, specifically when it comes to how to select an M&A advisor. Most advice that I’ve come across in this domain is frankly too high level to be useful, so today I wanted to get really detailed on how to select an M&A advisor, how much you shou...
2022-09-01
1h 07
In The Trenches
Strategic Considerations When Evaluating a Letter of Intent to Sell Your Business
For many business owners, few things are as exciting as receiving a Letter of Intent (“LOI”) from a prospective purchaser. Beyond the sense of validation stemming from the fact that a sophisticated counterparty sees an asset worth paying for, many business owners likely view an LOI as a just reward for decades of hard work, sacrifice, and illiquidity. Understandable as these reactions may be, I would argue that they are premature at best, and misleading (or even incorrect) at worst. This audio blog attempts to speak to prospective sellers of small or medium-sized businesses about what L...
2022-08-04
15 min
How2Exit: Buy, Don't Build - M&A of Small Businesses
How2Exit Episode 54: Steve Divitkos - Founder of Mineola Search Partners and a Search Fund Investor.
Mineola Search Partners is a firm that invests in Search Funds, the entrepreneurs who run them, and the companies that they acquire.Prior to Mineola, Steve was the CEO of Microdea, a document management and workflow automation software company serving the transportation and logistics industry. Steve acquired the business from its original founders in 2014, and successfully sold the company to a strategic acquirer in 2020 after having served as its CEO for approximately seven years. During Steve’s tenure as CEO, Microdea’s equity value quadrupled, providing his investors with a 20% compounded annual return on their original investment. In his...
2022-08-03
58 min
Top M&A Entrepreneurs
Searcher to CEO and Exit to Search Fund Investor, Steve Divitkos Top M&A Entrepreneurs
Take the Business Buyer Readiness Assessment → Jon talks to Steve Divitkos. Steve was in PE, became searchers, acquired a company, grew it, sold it, and is now the Founder of Mineola Search Partners, a company that invests in Search Funds, the entrepreneurs who run them, and the companies that they acquire.Show NotesIntro: 00:0000:45 Where did you start and why become a searcher?02:32 What is search fund - what is your cut of acquisition04:48 Why would a search fund investor install you as CEO with Z...
2022-07-25
37 min
In The Trenches
All Things Finance & Accounting: Managing Cash & Liquidity, Employee Financial Literacy, Capital Allocation, Preparing for Macroeconomic Turbulence, and Hiring Your First CFO
Today's episode is all about the finance & accounting function: My guest is Nicholas Andrews, who is the Founder of Aspen Consulting Group, a company that performs finance, accounting, and operations consulting for a wide range of small and medium sized businesses. Aspen’s services include technical accounting, corporate finance, valuations, operations planning and M&A due diligence, among others. Our conversation begins with several questions about how to manage cash and other sources of liquidity amid all of the macroeconomic volatility & uncertainty we’re currently witnessing. We then discuss the topic of employee financial literacy, including the question of how tran...
2022-07-21
1h 16
In The Trenches
Busting the Biggest Myth About Purchasing and Operating Small Companies
In this episode, I attempt to debunk a common misconception among prospective acquirors, particularly those looking to purchase a business for the first time. This myth states that the smaller the business in question, the easier it is to purchase and operate. In the material that follows, I will attempt to explain why the exact opposite statement is likely true: That smaller companies are actually much harder to both purchase and operate when compared to their larger peers.
2022-07-07
13 min
In The Trenches
Running a Business During Inflationary Periods and Understanding Pricing Power (with Jim Sharpe)
My guest today is a particularly personal and a particularly special one for me: I have been fortunate to call Jim Sharpe a mentor and friend for over 10 years now, and I am thrilled that he agreed to join the podcast. In this week's episode, we discuss the realities of running a business during high inflation environments, including the risks and opportunities that may present themselves during such times. We also discuss how CEOs should think about pricing their products and services in response to inflationary pressures, and finally how they should deal with vendors who attempt to pass through...
2022-06-23
1h 01
In The Trenches
The Biggest Temptation of a Software CEO
In his book, The Five Temptations of a CEO, author Patrick Lencioni discusses five areas in which CEOs tend to inadvertently prioritize the wrong things. These “temptations”, as he calls them, can lead to poor decision making at best, and can risk the very survival of the company at worst. My experience leading a software company taught me that there is a sixth temptation, unique to software, that seemed to present itself on a near-daily basis. More specifically: The biggest temptation of a software CEO is to throw bodies (specifically engineers) at problems. It is this...
2022-06-09
15 min
In The Trenches
Employee Burnout and The Great Resignation
My guest today is Carin-Isabel Knoop, Executive Director of the Harvard Business School Case Research & Writing Group. Carin has spent decades writing cases on managers and leaders all over the world, across a wide array of functions and industries. In 2019, alongside co-author John Quelch, she published Compassionate Management of Mental Health in the Modern Workplace, a book that dove deeply into the relationship between work life and mental well-being, and suggested in which managers can and should act as the "chief mental health officers" of their respective teams. In today's episode, we dive deeply into the following qu...
2022-05-26
1h 08
In The Trenches
Should You Become an Entrepreneur?
Today's episode is aimed towards those who may be wrestling with the question of whether or not to finally pursue their entrepreneurial dreams. I walk you through how I made this decision myself in 2012, and also attempt to compliment those considerations with some of the lessons and reflections that I’ve garnered in the 10 years since then, which of course benefit from the clarity that only seems to come with hindsight. Whether or not to take the entrepreneurial plunge is a deeply personal question, and as a result no objectively correct answer exists to address it. What I argue in thi...
2022-05-12
20 min
In The Trenches
Having Hard Conversations (Live Panel Discussion from 2022 MIT Sloan Search Fund Summit)
In this week's episode, we discuss the importance of having difficult conversations, something that CEOs find themselves doing on a near-daily basis. We discuss three primary types of difficult conversations, including a) Hard conversations around internal company dynamics (eg: terminations); b) Hard conversations about dynamics external to the company (eg: politics); & c) Difficult conversations that CEOs must sometimes have with themselves (eg: how and when to ask for help). This is a particularly special episode of In The Trenches for a number of reasons, including: It is our first ever video podcast! (Video available only through...
2022-04-28
1h 00
In The Trenches
A Leader’s Most Important Skill
My experience as a CEO taught me that the most important skill for any leader to possess is that of clear and effective communication. Indeed, a CEO’s strategy is only as good as her ability to communicate it. Though some of the basic tenets of effective communication are obvious and intuitive, others are less so. My experience leading a company over many years illustrated that good organizational communication often went well beyond the basics. In this episode, I will share with you some of the most important lessons that I learned about effective communication within my own company, including if...
2022-04-14
16 min
In The Trenches
Quality of Earnings Analysis: What You Need to Know Before Buying a Business
My guest today is Chris Hutchinson, a Partner in Ernst & Young's Transaction Advisory Services Group. Chris has over 15 years of experience advising clients on M&A, financings, valuation projects, and due diligence mandates, with a specific focus on private lower-middle-market businesses. Chris and his team have completed an untold number of Quality of Earnings ("QofE") mandates spanning countless industries, including software, technology, business services, distribution, and retail, among others. Chris and I discuss what a QofE is, why it's necessary, and common trends and themes that buyers should look out for. We also discuss the working capital adjustment: What it...
2022-03-31
1h 01
In The Trenches
Lessons Learned in Capitalizing an Acquisition
Among the myriad variables that must be carefully considered when acquiring a business is the question of how the acquisition is going to be financed. In today's episode, I will provide you with an overview of the specific lessons that I learned when financing my own acquisition in 2014. I begin by discussing the critical importance of the link between capital structure and strategy, and then discuss more specific lessons learned in raising the debt required to finance the acquisition. Please enjoy!
2022-03-17
21 min
In The Trenches
Aaron Ross: Author of "Predictable Revenue" and "From Impossible to Inevitable"
Though Aaron Ross wears many hats, he is perhaps best known for co-authoring the global best seller Predictable Revenue, often referred to as “The Sales Bible of Silicon Valley,” which details an outbound prospecting system that’s created more than $1 billion across Salesforce.com and other companies. Most recently, Aaron published From Impossible to Inevitable, a book co-written alongside Jason Lemkin (serial tech entrepreneur, venture capitalist, and founder of SaaStr.com, the world’s #1 resource for SaaS entrepreneurs), which is a "hypergrowth playbook" based on the successes of companies like Twilio, HubSpot, Marketo, and Salesforce.com. In addition...
2022-03-03
51 min
In The Trenches
The Entrepreneur and the Spousal Relationship
The role of spouse to an entrepreneur or CEO is not an easy one, as they are directly impacted by the emotional high and lows that are typical of the journey: They act as a source of consolation during the bad times, keep us grounded during the good times, and in many cases play a large (though often unnoticed and under-appreciated) role in our ultimate successes and failures. In spite of the importance of the role that spouses play however, the role of a spouse or partner in the entrepreneurial journey is a very under-discussed topic, at least within the...
2022-02-17
21 min
Acquisitions Anonymous - #1 for business buying, selling and operating
Analyzing Software Businesses for Sale with Steve Divitkos, experienced industry CEO - e66
We're joined this week by Steve Divitkos, Search Fund Investor & former CEO of Microdea.Steve has a background in private equity investing and after attending Business School he funded a Search Fund in 2012. He is originally from Canada.We examine two Saas businesses currently for sale.Thanks to our sponsors!Trout CPA is a full-service accounting firm offering M&A specific services of valuations, quality of earnings studies, and due diligence review services.The BEYOND8figures podcast (Beyond8Figures.com...
2022-02-08
47 min
In The Trenches
Bob Pritchett: Author of "Fire Someone Today" and Founder & Executive Chairman of Faithlife Software
My guest today is Bob Pritchett, and I’m really excited to be sharing this episode with you. Bob first came on my radar when I read his book titled “Fire Someone Today”, which was published in 2006. Right before I purchased my first software company, one of my investors and mentors purchased the book for me as a gift, and promised me that, in spite of the fact that I had likely never heard of the book, it was full of countless gems for entrepreneurs and CEOs running SMBs. And he was right: Fire Someone today remains one of my favori...
2022-02-03
1h 14
In The Trenches
The Working Capital Adjustment
The Working Capital Adjustment is part of substantially every M&A transaction, yet it is the calculation (and concept) with which most business owners remain largely unfamiliar. Without a proper understanding of what the working capital adjustment is, why it's necessary, and ways in which it can be manipulated, business owners risk leaving a lot of money on the table when dealing with a more sophisticated and experienced counterpart (even AFTER the sale of their business is already complete). If you don't like the idea of having to wire money back to your buyer after they've wired y...
2022-01-20
12 min
A Dealmaker's DNA with Ilan Jacobson
Episode 45: Steve Divitkos
Are you running on autopilot? Do you know how to turn off the autopilot? Today’s guest says that people spend more time on autopilot than they’d like to think, and it can prevent them from getting on the right path. Listen in to this interview with Steve Divitkos, an entrepreneur and the former CEO of Microdea. In this episode, you’ll hear about how Steve views entrepreneurship, why introspection is so difficult, and what Steve did right and wrong as a new CEO. Topics Discussed in This Episode How Steve was expo...
2022-01-11
35 min
In The Trenches
All Things Hiring with Randy Street: Co-Author of " Who: The A-Method for Hiring" and Vice Chairman of ghSMART
Today’s episode is all about Hiring, and we’ve managed to secure one of the world’s foremost experts on the subject. My guest is Randy Street. Randy is Vice Chairman of ghSMART, which is a global consulting firm that helps CEOs, boards, and investors build valuable companies specifically through hiring and developing world class leadership teams. During Randy's tenure, ghSMART has grown tenfold, and has been ranked by Forbes as one of America’s Best Consulting Firms from 2017-2020. Randy first came on my radar when I read the book that he wrote in colla...
2022-01-06
1h 10
In The Trenches
Considerations Unique to Acquiring a Software Company (Product)
In today's episode, I discuss the signs that prospective acquirors should look out for when attempting to uncover how much “technical debt” any given target company may possess within their 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 ship code less frequently, struggle to keep pace with competitors, regularly miss release targets, and are generally much more expensive and capital intensive to operate and grow. In this way, what start out as technical problems quickly accumulate to become significant business problems. Thus, pros...
2021-12-23
27 min
In The Trenches
Verne Harnish: Founder of The Entrepreneurs' Organization (EO), Author of "Scaling Up" and "Mastering the Rockefeller Habits"
Verne Harnish quite literally wrote the book (or, in his case, books), on being an entrepreneur and CEO running a small to medium sized business. Verne is the founder of the world-renowned Entrepreneurs’ Organization ("EO"), a global network of entrepreneurs and CEOs that boasts over 16,000 members worldwide. For the past 15 years, Verne has chaired EO’s premiere CEO program, the “Birthing of Giants” held at MIT, a program in which he still teaches today. Verne is also the Founder and CEO of Scaling Up, a global executive education and coaching company with over 200 partners on six continents. Verne may be best kno...
2021-12-09
1h 00
In The Trenches
Implementing a Formal Operating System Like EOS or the Rockefeller Habits
Throughout recent history, there has been substantial growth in the number of companies who have decided to implement formal “operating systems” to govern certain strategic and operational decisions within their businesses. Though there are many operating systems in existence today, two of the most widely used systems are EOS (based on the book Traction, by Gino Wickman) and The Rockefeller Habits (based on the books Mastering the Rockefeller Habits and Scaling Up, both by Verne Harnish). I implemented an operating system (EOS) in my own company beginning in 2015, and we continued to operate under its various principles and structures until succ...
2021-11-25
15 min
In The Trenches
The Realities of Managing Extremely Rapid Growth
Today’s show is all about GROWTH. Specifically, I want to dig into the personal and professional realities of running a high growth company that often aren't terribly visible from the outside looking in. Today, I talk to Anthemos Georgiades (or Anth, for short), who is the founder and CEO of Zumper, an apartment rental platform based out of San Francisco. If anybody knows about running a rapidly growing company, it’s Anth. Consider this: Despite being founded less than 10 years ago in 2012, Zumper now boasts over 250 employees and 75 million active users, making it the biggest residential rental platform in North...
2021-11-11
1h 19
In The Trenches
Considerations Unique to Acquiring a Software Company (Financial)
Acquiring any business is hard. Acquiring a software company is no exception, and indeed may prove to be even more intimidating to the inexperienced acquiror due to certain non-obvious considerations unique to software companies and the business models under which they operate. In this audio blog, I explore several of these unique and non-obvious considerations for the prospective software acquiror to consider based on my own experience acquiring, running, and selling a small- to medium-sized software company over the course of many years. Specifically, for every topic that I profile, I discuss why it’s important to dig one level de...
2021-10-28
18 min
In The Trenches
What M&A Lawyers Want CEOs to Know About Selling Their Companies
Today's episode is all about the legal issues and considerations involved in selling a small to medium sized business ("SMB"), many of which tend to be unfamiliar to CEOs and Entrepreneurs. My guest, Mario Nigro, is one of Canada's preeminent M&A lawyers, and currently serves as a Partner in the Mergers & Acquisitions and Private Equity & Venture Capital Groups at Stikeman Elliot based out of Toronto. From a legal standpoint, Mario has worked with substantially every type of stakeholder within the SMB ecosystem (business owners, CEOs, entrepreneurs, strategic acquirers, private equity firms, banks, non-bank lenders, financial advisors, d...
2021-10-14
1h 17
In The Trenches
Lessons From my First Month as the CEO of a Newly Acquired Company
In January, 2014, I became the CEO of a software company (after having acquired it from its original founders), powered by all of the wisdom and experience that one would expect from a 27-year-old who had never managed as much as a fruit stand in his entire life. The pace was intense, the volume of information to be processed was overwhelming, and the lessons learned were numerous. In this audio blog, with the benefit of 10 years' worth of hindsight and perspective, I attempt to share with you some of the major lessons and observations gleaned from my few months as the...
2021-09-30
20 min
In The Trenches
Rich Manders: Lessons from Founding, Growing, Buying, Selling, Coaching, and Investing in SMBs
My guest today is Rich Manders, who has essentially done everything that a CEO and Entrepreneur can do: He has founded companies, operated and grown them substantially, sold them (several times), acquired them (several times), and now acts as a coach for other CEOs and Entrepreneurs looking to do the same. Rich Co-Founded and led iAutomation, a Massachusetts-based machine control and automation company, and grew the company from $0 to $90M in sales with 180 employees. After selling that business to The Riverside Company (a leading global Private Equity firm), Rich stayed on with the business, and alongside his p...
2021-09-16
1h 27
In The Trenches
Why Your Business Needs a Set of Core Values (or Why Yours May Not be Having an Impact)
Early in my tenure as a CEO, I thought core values were tired, hollow, and meaningless platitudes that companies created simply because they felt they had to. Many of you may view them in a similar light. What I came to learn over time however was that my skepticism towards core values wasn’t because the CONCEPT of them was hollow and meaningless, but instead because so many companies had done such a poor job in establishing theirs, and as a result, their core values BECAME tired platitudes that nobody paid attention to. We ev...
2021-09-02
12 min
In The Trenches
Building and Managing a World Class Product Management Discipline
Today’s episode is specific to software companies, and is all about the Product Management operation. As most software executives can attest to, a non-functioning (or worse, a non-existent) product management operation can get companies into all kinds of trouble, and those problems often manifest across Engineering, Sales, Customer Support, and other areas. Some software companies, particularly more mature ones, often start out without a formalized product management discipline, but companies who pursue any degree of scale often quickly realize just how critically important this discipline is. My guest today is Rich Mironov, who is...
2021-08-19
1h 04
In The Trenches
Busting the Biggest Myth About Selling Your Business
As a business owner, if you're thinking about the sale of your company as being the singular event that will finally eliminate all of the risks that you've personally assumed for so many years, then I hate to be the one to tell you this, but: Think again. Indeed, in my experience, the single biggest myth about selling a company is that the seller bears no further risk after the sale of his or her company is completed. In most cases, especially with respect to the sale of SMBs, this is simply not true. In this audio blog, I will sh...
2021-08-05
23 min
In The Trenches
Understanding and Managing The Psychological Toll of Being an Entrepreneur or CEO
In today's episode, I speak with Dr. Eliana Cohen, a Clinical Psychologist who works with (among others) a wide variety of Entrepreneurs and CEOs. Dr. Cohen's practice integrates performance psychology, strategy, emotional intelligence, and knowledge of neuroplasticity and the brain to serve her various clients. In our discussion, we cover a lot of ground including the psychological similarities that Entrepreneurs and CEOs tend to present, how to differentiate between healthy and unhealthy levels of worry and/or anxiety, how leaders tend to conflate their own happiness with the success of their businesses, signs to watch that may suggest that m...
2021-07-22
1h 21
In The Trenches
Lessons in Managing my own Psychology
Ben Horowitz, the former CEO of Opsware and now world-renowned Venture Capitalist, once said: “By far the most difficult skill for me to learn as CEO was the ability to manage my own psychology . . . very few people talk about it . . . In the end, this is the most personal and important battle that any CEO will face.” I suspect that almost all entrepreneurs and CEOs know exactly what he meant when he said this. My own experience taught me that unless you are deliberate about managing your own psychology as a leader, you risk becoming a sort of “victim”...
2021-07-08
21 min
In The Trenches
CEO Coaches: What do they do, how do they work with CEOs, and why might you consider hiring one?
In this episode I interview Warren Coughlin, who has been a Coach to SMB CEOs for upwards of two decades, helping them achieve everything from hugely successful exits, to 7-figure salaries, to significantly reduced day-to-day operational roles, and countless other outcomes. Warren is the creator of The Business That Matters Playbook, a tool that streamlines and automates the strategic planning process for CEOs and Entrepreneurs. His coaching practice focuses not only on the business itself, but also on the entrepreneur at a personal level, working with them to ensure that they craft meaningful values and live a...
2021-06-24
1h 09
In The Trenches
Migrating Your Software Company from On-Premise to SaaS (Part 2)
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 through the tactics and strategies that you can put into place to make your own t...
2021-06-10
22 min
In The Trenches
What I Learned During my First (Failed) Attempt to Sell my Business
As CEOs, many of you are 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 process. Just as we were beginning to draft the final purchase agreement, the transaction fel...
2021-06-04
24 min
In The Trenches
Considerations in Selecting Your M&A Advisor
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 have an enhanced appreciation for the specific variables...
2021-06-02
21 min
In The Trenches
Pricing Power: How Small Changes Can Have Big Impacts
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 opportunity that may reside within the base of customers that you already possess. ...
2021-05-31
17 min
In The Trenches
The Private Equity Perspective on Acquiring, Operating, and Selling Software Companies
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 serves on the Board of Directors of 5 private technology businesses, and through Radian has made direct investments (both majority and minority...
2021-05-27
1h 28
In The Trenches
Migrating Your Software Company from On-Premise to SaaS (Part 1)
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 company still selling on-premise software under a perpetual-use pricing model (or is considering investing in one) , I'd humbly suggest that yo...
2021-05-26
24 min
In The Trenches
Hiring Your Senior Leadership Team
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 mistakes) to learn about gre...
2021-05-17
20 min
In The Trenches
Why So Many Companies Rarely Achieve Their Annual Goals
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 experience (and in the experience o...
2021-05-17
22 min
In The Trenches
The Entrepreneur and Mental Health (Part 2): My Advice to You
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 practical, and full of strategies that you can actually...
2021-05-13
16 min
In The Trenches
The Entrepreneur and Mental Health (Part 1): My Journey
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 less practical for yo...
2021-05-13
19 min
In The Trenches
Sales: Hiring, Onboarding, Compensating, Scaling & Supporting a World Class Sales Team
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 average 50% revenue CAGR for 9 of his 10 years. Dave played an in...
2021-04-29
1h 29
In The Trenches
In The Trenches (Trailer)
2021-04-19
00 min