In The Trenches

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 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 operation, including countless searchers and CEOs within the ETA community. * When acquiring small to medium sized businesses, buyers often utilize a tool called an “earn-out”, which is a form of contingent consideration that sellers may receive at some point in the future in addition to the cash that they stand to receive at closing. Though earn-outs can be useful and mutually beneficial tools for both buyers and sellers under the right circumstances, without careful structuring and consideration they can fraught with risk and unintended consequences. Before you propose an earn-out as part of your own acquisition, I’d encourage you to think through some of the risks and considerations that we discuss in today's episode. Please enjoy!

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 ⁠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. * My guest this week is Andy Johns, whose memoirs could be titled "a tale of two careers". In his "first" career, Andy was an executive within the start-up and technology ecosystems, with growth and product oriented leadership roles at Facebook, Twitter, and Quora, among others. Following his time at these three companies, Andy became VP of Growth, VP of Product, and eventually President at Wealthfront, an automated investment platform that currently boasts $27 billion AUM across 470,000 accounts. Now, in his second act, Andy spends his time helping others heal from emotional pain, transform themselves, and discover their life purpose. He is the Founder of clues.life, an online collection of wisdom, information, stories, and research on mental health, personal transformation, and the pursuit of meaning and purpose. He is also the author of a very popular substack, where he writes about the mental health struggles often faced by high achievers like himself.

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 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! * Though search funds have historically acquired companies within countless different industries, software has been among the most popular and sought-after industries among searchers for many years now. Because of this, I chose to conduct a survey of SaaS CEOs (who became owners/CEOs by way of the search fund model) for two reasons: (1) To better understand the complexion of the "typical" software acquisition within the search fund ecosystem; & (2) To see whether or not the the complexion of the "typical" software acquisition has changed over time. As you will see from the data presented in today's episode, I feel safe in concluding that, yes, the profile of the typical SaaS acquisition has indeed changed over the past few years, in some cases quite materially. Today's episode will walk you through how and why I arrived at this conclusion. *Special Note for today's episode*: Because this post is necessarily heavily on stats and graphs, I would strongly suggest viewing the blog post (as I can only verbally describe graphs so well!), which you can find at this link.

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 their LinkedIn page to learn how they might be able to help you exactly as they helped me. * 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. * Today, I'm joined by Kent Weaver, somebody who has decades of experience serving on the Boards of SMBs. Kent is an acquisition entrepreneur himself, having acquired a Sacramento-based health care business after a ~2 year search. After running the company for close to 9 years, he exited successfully, and has been investing in SMBs ever since. He has invested in over 150 search funds and 80 operating businesses, and has served on over 25 boards spanning health care, software, business services and consolidation strategies. Given Kent’s depth of governance experience, I thought he’d make a great resource for current or prospective CEOs who might be wrestling with questions related to how to construct, communicate with, and learn from their own Boards. Please enjoy!

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 entrepreneurs persist at substantially any cost, or should they be wise enough to know when they’d be better off doing something else entirely? How does one know when to perceive persistence as an asset, and when to perceive it as a liability? In late-2020, I decided to step down as the CEO of my own company after approximately 7 years at the helm. Since then, I have spoken to countless entrepreneurs and CEOs wrestling with similar decisions. In each instance, they asked how I made my decision, which is why I’ve decided to write this post.  Though I can’t tell you specifically what you should do, I can at least share with you the questions that I asked of myself in coming to my own decision.

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 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 their LinkedIn page to learn how they might be able to help you exactly as they helped me. * Among the countless strategic decisions that software CEOs must make, the decision of which end markets to serve doesn’t seem to command the time, attention, and level of thoughtfulness that it probably should. More specifically, substantially every small or medium-sized software company must answer the following two questions: Should I sell to SMBs or to larger enterprises? Should I sell my product into a single industry vertical, or multiple industry verticals? Though these are of course not the only questions that software CEOs must answer with respect to the markets that they serve, they tend to be among the most important and most frequently posed ones. The purpose of this blog is to speak to both of these questions in turn.

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 their LinkedIn page to learn how they might be able to help you exactly as they helped me. * 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.  * My guest today is Dr. Noam Wasserman, recognized as one of the world's foremost experts in how to form and maintain high performing partnerships in entrepreneurial contexts. Dr. Wasserman is currently the Dean of the Sy Syms School of Business at Yeshiva University in New York City, and was previously a professor at Harvard Business School for 13 years. His now famous book, The Founder’s Dilemmas, quickly became an Amazon #1 bestseller, and has since won countless awards. In our conversation today, we discuss what to consider when seeking out a partner, the important conversations that prospective partners ought to have with each other, what role passion and persistence should play in the entrepreneurial journey, and how to apply his various concepts and frameworks to our personal lives.

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 their LinkedIn page to learn how they might be able to help you exactly as they helped me. * 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 that, Warren is offering $3,000 off of his coaching program for listeners of In The Trenches. Just go to warrencoughlin.com/trenches to learn more.  * Though there are countless books, blogs, podcasts, and social media accounts that serve as thoughtful and informative resources for current and prospective entrepreneurs, unfortunately there appears to be an equal number of resources that demonstrate seemingly no limit to the fundamentally bad advice that they’re willing to impart upon others. "Hustle Culture" has unfortunately become so prevalent online that I felt it necessary to provide the entrepreneurial community with my own perspective on the matter.

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 their LinkedIn page to learn how they might be able to help you exactly as they helped me.  * 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 that, Warren is offering $3,000 off of his coaching program for listeners of In The Trenches. Just go to warrencoughlin.com/trenches to learn more. * This is a very special episode of In The Trenches: In today’s episode, I will be interviewing 4 different CEOs of 4 different SMBs, and asking them just a single question: "What are some of the seemingly small changes you’ve made that have had the largest impacts?" When taking over a new business, new CEOs often speak of operational “low hanging fruit”, so I wanted to ask this same question to 4 different CEOs to learn more about just what this low hanging fruit is. Each CEO that I’ll be speaking with today is at a different stage of their journey: Betsy, who I’ll begin the episode with, is still in her first year in the CEO seat. Sheret, our next leader, has been CEO of his company for ~2 years. Robin Kovitz has been leading her company for ~8 years, and finally Adrian, our final CEO, ran his company for ~7 years before a successful exit to a strategic acquiror in 2019. Does growth and success tend to result from a large number of seemingly small changes, or a small number or larger changes? That’s what we’ll endeavor to answer today, informed by 4 CEOs at very different stages of their respective journeys.

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 that, Warren is offering $3,000 off of his coaching program for listeners of In The Trenches. Just go to warrencoughlin.com/trenches to learn more. * 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.  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 Crossing is offering a special discount to listeners of In The Trenches: Just go to caynecrossing.com, and scroll down to the “contact form” on their homepage. Enter the offer code “trenches”, and you will get a full $2,000 off of your QofE engagement with them. * CEOs running newly public companies, those who have raised external equity for the first time, and those occupying the CEO seat for the first-time are often intimidated by the idea of reporting into a Board, and are uncertain of how to construct, manage, communicate with, and learn from them. This combination of uncertainty and inexperience often creates undue stress for CEOs, and can create situations in which they are more focused on impressing their Boards than they are on leaning on them for support, guidance, and mentorship. Over many years as a CEO reporting directly into a Board (and now as an investor who sits on Boards and works directly with CEOs myself), I’ve come to learn a few things about how to construct, manage, communicate with, and learn from this critically important group of people. This episode is my best attempt at sharing these lessons with you.