This is the last of a six-episode series with Trilogy Search Partners focused on Search, Search-backed acquisitions, and small business operations. Today we have a great conversation with Stijn Hendrikse, an operating partner at Trilogy.As an author of T2D3.pro, serial entrepreneur, and marketing leader, Stijn has contributed to the success of 10+ startups as a C-level executive, including the Chief Revenue Officer of Acumatica and CEO of MightyCall, a SaaS contact center solution.Stijn founded Kalungi - the global leading Growth-as-a-Service provider focused solely on B2B SaaS companies, and Amy.us, an AI-powered conversation platform that allows small business owners to service their customers better.Before focusing on startups, Stijn led global SMB Marketing and B2B Product Marketing for Microsoft’s Office platform.Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. Links:Stijn on LinkedInTrilogy Search PartnersBrowzwearTopics:(1:53) - Breaking down the SAAS business model(4:22) - What are some of the SAAS companies and marketing teams you’ve been a part of over your career?(7:20) - What led you to ultimately work with Search Funds?(11:22) - What kinds of companies do you encourage Searchers to look for?(13:50) - How do you value the effectiveness of a marketing function in a company?(20:03) - Where can early CEOs improve on pricing?(25:58) - Do you recommend any proactive communication cadence with customers?(30:45) - How do you start developing a high-performing marketing function? (33:38) - When does bringing on a fractional CMO make sense?(35:24) - What’s the best mix long-term for in-house marketing vs. outsourcing?(37:36) - How do you find the right person to grow within your marketing function(42:17) - What strategies do successful CEOs use to help get teams behind their vision?(43:49) - What’s really important to know about the Ideal Customer Profile?(48:25) - How do you develop an effective outbound campaign?(57:36) - How incoming CEOs can add value

Today’s episode is a rerun with past guest Ross Brendel, a co-founder and the managing partner of Westerly Group alongside cofounder Rich Littlehale. Westerly Group invests in acquisition entrepreneurs with committed, permanent capital to pursue a specific industry thesis over an indefinite time horizon. They are investors in several of our podcast guests such as Justin Vogt and Ed Redden, Eric Factor, and Austin King, among others.I wanted to bring this episode back to your attention as permanent capital and longer time horizons are becoming more talked about today and I think it’s important to discuss the nuances of this approach, as Ross does in this episode.In this conversation, Ross shares Westerly’s permanent capital thesis and model, whether buying a business has become harder or easier, how to think about a purchase price with a longer-term view, and the nuanced advantages of committed capital in pursuing acquisitions.Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. Links:Ross on LinkedInWesterly GroupSylmar GroupEra Services GroupEvermore IndustriesNorthrim HorizonBusiness Model GenerationTopics:(3:32) - Ross’ background & career(6:39) - Why do you think interest in longer-term hold vehicles has increased in the past few years?(9:33) - Should entrepreneurs be less price-sensitive when looking to buy a business?(11:36) - How do you find entrepreneurs with the right mindset when buying a business?(13:42) - Do you think buying a business has gotten harder over the past 5-10 years?(18:46) - What are some of the unique ways you’ve seen Searchers find companies to buy?(20:25) - Can you tell us about some of the teams you’ve backed?(23:19) - Can you talk through some of the advantages of committed capital structures?(28:06) - Was it intentional to take a generalist approach to your work?(31:53)- What happens if an entrepreneur you back loses desire for the industry they initially start Searching in?(33:51) - Does your Zero Horizon Investor idea give you more flexibility in terms of the business models you go after?(37:18) - Are there any other models in Search that are interesting to you?(39:36) - How do you think you’ll continue to find entrepreneurs and teams? Do you have a formulaic approach?(42:10) - What college class would you teach if it could be about anything?(44:12) - What’s a strongly held belief you’ve changed your mind on?(45:33) - What’s the best business you’ve ever seen?

My guest on this episode is Sandy Paige. Sandy has been an operator several times over his career, including being a general manager at a Maine paper mill, a director of The Jackson Laboratory, and others which gave him a wide range of experience to use in growing the company he acquired as a searcher, Explora BioLabs.He’s also an outlier in being one of, if not the, oldest searchers. But his results speak for themselves: Sandy grew Explora BioLabs over the course of 4 years starting in May 2018 to sell for $295 million in April 2022.Sandy and I talk about the importance of communication as a CEO and his philosophy behind it, how he sought and hired managers who could grow with the company, early career CEO mistakes to avoid, communicating with your board, and his priorities and focus in the CEO role.Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. Links:Check out this podcast for a deeper dive into Sandy's backgroundThe Jackson Laboratory Explora BioLabsSandy on LinkedInTopics:(2:58) - Can you give us your background and career to this point?(6:36) - How did the paper mill experience influence your management style?(10:45) - What were some of the characteristics of bosses you worked for that you tried to emulate?(12:43) - Are there skills that helped you refine your best qualities as a manager?(15:30) - What do you look for when hiring?(18:54) - What do you think early career CEOs often miss in management hires?(21:56) - Are there questions or techniques you use to inform you the hire is a hard worker?(24:14) - What started to happen after those hires?  (27:41) - As your company grew, how did your team structures have to change?   (33:45) - How do you position a company so that it increases enterprise value?(35:39) - What made it so different for you?(37:52) - Did you find it challenging to run the business while going through diligence?(40:08) - What was your set of responsibilities and priorities as a CEO?(42:03) - What kind of communication cadence did you have with your board?(45:08) - How do you ask good questions to your board?(46:34) - Is there any advice you often give to early career CEOs?(48:21) - What strongly held belief have you changed your mind on?(49:48) - What’s the best business you’ve ever seen?

My guest on this episode is Michael Coscetta. Michael has held several high-level sales roles at companies like Square, Compass, his own company, and his current role as CRO of Paxos, and through it all has become an expert in designing and managing sales teams.This was a fantastic conversation about all things sales and building sales teams and is one I will be re-listening to several times over the coming years. While a large portion of Michael’s time has been spent in very large sales organizations, the principles he talks about are still widely applicable in companies of any size, and all regular listeners to this podcast are in for a treat.Michael and I talk about writing high-value sales contracts, the growing importance of high-performing sales operations, how sales have become data-driven and more quantitative, how to recruit for sales, and the leadership of sales.One final note before the episode, I want to meet more sales professionals, especially in data and data software. If you, or someone you know, have expertise in data enterprise sales I would love the chance to connect. You can find me on my website alexbridgeman.com, LinkedIn, and Twitter, or send me an email directly at alex.e.bridgeman@gmail.com. Thank you, I look forward to chatting soon!Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. Links:PaxosMichael on LinkedInSuperhuman's Fundraising Playbook with CEO Rahul Vohra on the Acquired PodcastOn Revenue Quality with Bradley Roofner and Logan Brown - Ep.145 of TLAOTopics:(4:32) - Michael’s background and career(7:03) - Are there any common principles you’ve picked up over the course of these vastly different experiences?(9:28) - What have learned about building valuable sales contracts?(12:42) - What processes or strategies have you developed to find the right pricing matrix arrangement?(15:49) - Are there any questions you ask customers to find optimum pricing?(18:55) - Have you seen an evolution in how sales teams are viewed in companies?(22:04) - Is there any data set that has the most impact on a sales team?(24:37) - What are the differences between sales orgs of less than 50 people and larger ones?(27:33) - How do you go about setting sales goals?(30:38) - Do you have a sense for trigger points for when you separate different parts of the sales process into their own individual teams (32:42) - How do you view renewals or upsells for existing customers vs. new ones?(33:57) - What personalities or characteristics work best for filling out different sales roles? (40:31) - Are there any helpful questions or interview styles to determine whether a candidate is a good fit?(42:57) - What are some best practices for making sure sales and products are communicating effectively?(45:57) - Are there any communications methods that work well with customers?(48:51) - How does the product team decide what customer feedback is valid and what is noise?(53:09) - In this environment, how do you continue to build and improve your sales team?(55:54) - Can you expand on the concept of the sales org being the brains of a revenue organization?(58:00) - How can a CEO get more involved with their sales team in a non-disruptive way?(1:00:16) - What strongly held belief have you changed your mind on?(1:01:11) - What’s the best business you’ve ever seen?(1:04:06) - What other companies do you study and admire for their sales org?

My guest on this episode is Nick Buchanan. Nick and his father founded a data software business called BUCS Analytics in 2006. BUCS builds deep analytical dashboards for CEOs that pull from internal data sources like ERPs, inventory systems, and more. Long-time customer Trevor Flannigan, COO of the Flint Group, introduced us after hearing about my deep curiosity of data companies.Nick and I talk about building the company with his father, building momentum in product development and sticking close to customers, hiring a talented team, and how to find groups and peers to help guide your entrepreneurial journey.Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. Links:Nick on LinkedInBUCS analyticsSean Joy – CEO Journey within Chenmark – Ep.152Timestamps(00:00:00) Intro(00:02:15) What is Bucs Analytics and the founding story? (00:07:35) Are there any industries you’ve specialized in?(00:09:38) Can you walk through product development?(00:13:11) How do you decide on outcomes of experiments where results come out similar?(00:16:25) Are there 2-3 ways you measure engagement and value? (00:17:41) What’s been the process of evolution on the sales side? (00:20:53) What are the channels you’re hoping to develop further?(00:22:13) What are the benefits of having a group of peers over time? (00:25:34) Is there one change or development in your peer group that’s helped the most? (00:27:35) Where was your mindset when starting Bucs and how has it changed over time?(00:29:19) What are some of the most successful ways you’ve found to attract and keep talent at Bucs?(00:32:21) What does it look like fulfilling a new employee’s goals? (00:34:46) What’ve you learned the most about managing change in a company? (00:36:37) What’s your philosophy for setting goals? (00:39:21) Have you ever made secondary adjustments to annual goals?(00:40:30) What goal do you feel you’re the most excited to achieve this year? (00:41:13) What strongly held belief have you changed your mind on?(00:42:40) What’s the best business you’ve ever seen?

My guest on this episode is Carl Streck, founder and CEO of MountainSeed, a data and software business serving commercial real estate professionals. I was introduced to Carl by Michael Arrieta after asking Michael for the most interesting entrepreneurs in data he knew of, and Carl’s name was the first out of his mouth. Carl started MountainSeed in 2006 to build software serving banks making commercial real estate loans and eventually developed a data product to help banks make more data-driven decisions.Carl and I talk about bootstrapping a data software company, evolutions in his management style as the company grew, the business models of data companies, and how staying close to customers impacted the development of their data product. Enjoy!Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. Links:Carl Streck on LinkedInMountainSeedEOSWhat Got You Here Won't Get You There by Marshall GoldsmithYPO.orgThe Economics of Data Businesses by Abraham ThomasCraig Fuller on TLAOTopics:(2:46) - How has your thought process around raising capital changed over the years?(5:43) - Does your mindset towards capital change when it comes to accelerating growth vs. starting growth?(8:03) - What have you learned from peers or your own experience in finding the right investor/company fit?(10:29) - What was your role and how did it evolve during different stages of team size in the organization?(14:16) - As companies grow, where do you see CEOs and founders start to struggle?(17:46) - Is there a way to build a culture that encourages feedback they might not want to share otherwise?(21:05) - What are some of the most impactful behavioral changes you’ve made to build trust and feedback with the team?(25:43) - When you study CEOs of larger companies, what is different about how they operate as leaders?(28:23) - Can you walk us through how you view your product portfolio and how the two work together?(32:40) -How do you compare SAAS businesses to Data Businesses?(35:56) - Does your Data Analytics platform work within the platforms or software of customers?(38:23) - How would you categorize the customers of your product?(41:02) - Does the Analytics platform license 3rd party data sources?(43:19) - How are you looking to design and build a data company that lasts?(46:07) - How do you incorporate customer feedback or determine new features?(49:09)- What’s a strongly held belief you’ve changed your mind on?(52:24) - What’s the best business you’ve ever seen?

My guest on this episode is Sean Joy, CEO at Buccaneer Pirate and Southern Star Dolphin Cruise, a company owned by Chenmark in Destin, FL that provides seasonal boat tours. Sean was a part of Chenmark’s GVP, the Generalist Vice President program that provides a career track to becoming a CEO at a Chenmark company.Individuals start by working on a couple of projects within the portfolio, then take a non-CEO operating role in a company, before moving to a CEO role. Sean’s background was in control workouts and restructuring, which we talk about to kick off the episode before he found a small business in Chenmark and inquired about their GVP program.Over the course of the episode, we talk about Sean’s finance experience, what he pays close attention to given his restructuring experience, managing cash in a highly seasonal business, the wide array of services offered on a tour boat and how they interact, and the power of price increases. Enjoy!Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. Links:Sean on LinkedInSouthern Star Dolphin CruiseBuccaneer Pirate CruiseChenmarkTopics:(6:08) - What are some interesting lessons you learned and experiences in restructuring?(12:52) - What are some habits you have today as a CEO that you can tie back to prior experiences in restructuring?(14:40) - How did you connect with Chenmark and what about it was appealing to you?(16:52) - What were the roles you had when you first joined the organization?(20:27) - Were there any learning curves early on in your role as CEO?(22:06) - How much debt was in the business?(23:39) - What are some ways that you manage cash throughout the year with a heavily seasonal business?(27:33) - What are some of the add-on services you’ve implemented to increase revenue?(31:46) - What are your criteria for cutting vs. keeping products?(32:47) - How much time and energy do you spend on pricing your products?(38:10) - How dynamic is your pricing?(39:28) - What other improvements are top of mind for you?(46:26) - What strongly held belief have you changed your mind on?(48:51) - What’s the best business you’ve ever seen?

My guests on this episode are Heritage Holding co-founders Alex de Pfyffer and Ross Porter. Heritage acquires companies across industries, but has a special focus on IT services and data centers. I’m a data geek and love talking with entrepreneurs in data, and haven’t talked with much of anyone on the hardware side so this conversation was a lot of fun for me.We talk about identifying companies offering essential services, their data center acquisitions and strategy, what they’ve learned from private equity on growing companies, and thoughts on a long-term structure for Heritage going forward.Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. Links:Heritage HoldingAlex de Pfyffer on LinkedInRoss Porter on LinkedInTopics:(3:03) - What’s the background for Heritage and how did you each get to this point?(5:56) - What ideas were you considering for a startup?(7:57) - Have there been any guiding principals or common threads through the acquisitions you’ve done thus far?(11:49) - What does the data center business model look like?(13:53) - Is there some overlap with your ISP or Fiber investments?(15:00) - Is there some first mover advantage to bring Fiber Optic Cable to a certain area?(16:33) - Who is your typical competitor?(18:38) - Once you own an ISP, what are the ROI metrics for expanding that footprint?(20:27) - Where do you see other opportunities in data for investments?(26:10) - What have you learned from managing companies of different sizes?(34:09) - What changes the most when you go from $10m to $50m of EBITDA?(37:29) - What are some structure questions in your mind as you look to future acquisitions?(43:35) - What’s a strongly held belief you’ve each changed your mind on?(49:41) - What’s the best business you’ve ever seen?

My guests on this episode are Johnny Lieberman and Zack Miller, who together founded Worklyn Partners to acquire and grow cybersecurity and IT services companies. A concept we talk a lot about in the episode is how the two businesses create a flywheel between each other. I find these flywheels fascinating and I've talked about others such as the flywheel between media and data with FreightWaves founder Craig Fuller in Episode 121.Johnny and Zack share how the two business models function both together and independently, where growth is coming from and trends driving that growth, developing sales teams, and why only the paranoid survive. Enjoy.Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. Links:Johnny Lieberman on LinkedIn Zack Miller on LinkedIn Worklyn Partners Quadrant Information Security Topics:(2:41) - Can you walk us through the timeline of Worklyn and where you’re at today?(9:35) - How do your cybersecurity & IT platforms work collaboratively together?(11:07) - Why are you pursuing growth via acquisition on the IT side but not in cybersecurity?(17:07) - Is there a similar dynamic between sales in IT services and Cyber?(18:08) - How does the sales cycle work from getting an IT customer over to the Cyber side?(22:42) - What are some high-level industry tail winds you’ve observed?(29:49) - Could the flywheel between Cyber and IT extend to software businesses or service tools that could support the business?(33:59) - Within Worklyn, where do you see most of the value being created?(36:49) - How have you been working to attract great people to your teams?(40:01) - How have you structured management compensation?

My guest on this episode is Richard Reese. Richard took over as CEO of Iron Mountain, a physical records management business, in 1981. He ran the business as CEO through going public in 1996 before retiring from the role in 2013. Revenue over that period grew from around $3 million in 1981 to $3 billion in 2013.Our discussion focuses on incentivizing teams with cash and stock, something Richard has thought deeply about over many decades, developing compensation plans, working with private and public investors, and a few stories from the early years of running Iron Mountain.Listen weekly and follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. Links:Richard on LinkedInIron MountainTopics:(4:03) - Richard’s background, career, and time as CEO for Iron Mountain(14:03) - What became easier when you went public? What became harder?(17:30) - What did your management team look like when you stepped in and how did you look to evolve it?(24:29) - When you started thinking about incentivizing the management team, what were some ways you got them to buy in?(38:35) - What kind of challenges did you run into with equity compensations?