Learn how to acquire, grow, and invest in cash-flowing SMBs | Bought healthcare biz at 26, grew 8x by 31 | Subscribe to the SMB Scoop weekly newsletter

Joined April 2009
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PPP Data is a goldmine for a small business buyer - I shouldn't be telling you this... In less than 10 minutes, I found 95 'Flooring Contractors' in Texas, estimated their revenue & EBITDA based on their PPP loan data 6 steps: 1. Get PPP Payroll data for the specific NAICS industry code & geography into a spreadsheet 2. Calculate annual payroll (PPP loan is 2.5 months of payroll) 3. Estimate what payroll is as a % of revenue (this will be industry and biz) 4. Estimate annual revenue 5. Get estimated EBITDA (using your estimate of EBITDA margins typical for this biz) 6. Refine your list further by filtering by your minimum EBITDA threshold
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Will be some great insights shared by Chris if you are interested in the home services space
If you run a home service company (or aspire to someday), you need to read this. Here is why I am launching a newsletter on June 1 (subscribe in comments): Countless entrepreneurs are wanting to dive deeper into what it takes to scale beyond $100M… without raising capital. - how to blend “high performance” with a purpose driven culture - how to lead the way in technology artificial intelligence - where to invest… and what to avoid - how we design systems & processes to drive improvements in targeted KPIs - how we approach acquisitions our post-closing integration work - how I think about competing - and WINNING - in the face of intensifying competition from large consolidators - how we leverage our long term orientation to outperform our peers - how I think about working with family members to include my dad and brother - how we finance our business & investing activities … and many more tactical strategic insights. Grateful for my founding sponsors… really excited to share exclusive content in collaboration with category leaders across software, AI, financing, and more.
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Anyone use Ramp (@tryramp) for CCs and AP? Our cash balances required linked has increased 3x overnight after 2 years of being a client. 4 support tickers, some ignored, still no answers. Terrible communication. Can’t get to a knowledgeable support person Or is this just us?
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🔥 MSP owners: Still stuck in technician or fire fighting mode? Like the idea of delegating but it never actually happens? In this week’s MSP Owner Podcast, I sit down with Elmo Taddeo, owner and CEO of Parachute Technology — a $11.5M revenue MSP with 70 team members. Elmo breaks down the real shift that happens when you stop doing the work and start building the machine. We're talking about process & people, and most importantly LETTING GO. 👊 Delegation isn’t just about offloading tasks — it’s about building trust and creating freedom. We talk about a lot of other stuff too: EOS, marketing, how to target & find larger clients 50 users 🎧 Listen here → mspowner.com/episode/elmo-ta… 🎧 Youtube: youtu.be/u9Ok_sqpIR8 🎧 Spotify: open.spotify.com/show/0NskmB… 👇 Was there a moment when you truly started to delegate? Mine: I acquired a company years ago where it was too big (16) for me to do all the things myself, I HAD to rely on others from the start. Some small MSPs who start as 1 man bands, never get over that hump.
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I've struggled with change management and I need your help: Do you have a change management process within your company? What does it look like? Formalized? Only certain departments? Too much restrictions can turn you into a corporate beast. Too few restrictions means it's the wild west, communication is poor. Also, why does no one talk about this??? I see this become an issue when you have 40 employees it becomes a real pain point (especially if things worked well at 30 employees)
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🚀 I'm loving doing the MSP Owner Podcast. Today we just released an episode featuring Mike Beecher from EscapeWire Solutions. MSP owners sharing their story about how they got to where they are today, and it's working. We don't hold back on the topics & stuff we talk about - successes and failures. 🌍💻 Mike's journey is a true underdog story, filled with unexpected twists and turns. Mike is more of a business guy rather than a technical guy, which gives him a unique sales perspective and advantage. From a family business in equipment rentals to navigating the chaotic waters of the IT world, his insights on work-life balance and client relationships are both relatable and enlightening. Discover how Escape Wire adapted to the post-pandemic landscape, embracing remote work as an opportunity for growth. Mike and I talk about the how to maintain a strong company culture (essential to growing your MSP), ensuring every employee contributes to the mission. Listen in and let me know your thoughts & feedback :-) 🎧 Tune in now: mspowner.com/episode/mike-be… Youtube: youtu.be/JW-m2LUXgV8?si=pnjY… Spotify: open.spotify.com/show/0NskmB…
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🚨 Do you hate Microsoft Teams? 🚨 A lot of Twitter does for some reason. I'm going to be honest, it's a YOU problem (yes I'm looking at you @kelceylehrich). If you are running a modern business who cares even just a little bit about productivity & security, Microsoft & Teams is what you should be buying into. I'm hosting a webinar with my CISO Ernest Murry tomorrow to break down exactly how to make Teams work for your business—not against it. We’ve seen it done very poorly—bad buy-in, confusing structure, and disorganized workflows. In less than 30 minutes, we’ll show you the light and how to think about Teams the right way 💡 Registration link: events.teams.microsoft.com/e…
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🚀 New Episode of MSP Owner Podcast! 🎙️ In this episode, I sit down with Marco Hernandez, founder of TEK IT UP IT Services, a nimble one-man MSP based in Toronto, Canada. Marco's journey spans 25 years, three countries, and countless lessons on running an efficient, client-focused IT business. 🔹From law school dropout to IT entrepreneur 🔹Running an MSP as a solo operator—and making it work 🔹Transitioning from break-fix to managed services model 🔹The power of networking to grow an MSP 🔹Why he walked away from a high-paying corporate IT job after one day Marco’s story is a masterclass in resilience, adaptability, and strategic growth for MSPs. Whether you're a solo operator or scaling up, you’ll take away actionable insights from this episode. 🎧 Listen now: 👉 YouTube: youtu.be/q2It88KcG2c 👉 Spotify: open.spotify.com/show/0NskmB… 👉 Apple Podcasts: podcasts.apple.com/us/podcas… 👉 Subscribe for new episodes: mspowner.com/ What are your biggest challenges running an MSP? Drop a comment below! ⬇️
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Episode 2 of the MSP Owner Podcast just dropped featuring the wonderful Dustin Bolander of Clear Guidance. Dustin and I met for breakfast 6 months ago, and I left thinking...wow that guy sure does a lot of things. 🎙️🚀 Dustin’s journey from a 12-year-old helping his family business to building and selling multiple MSPs is packed with lessons on leadership, growth, and making bold moves. Here’s what you’ll learn: ✅ Starting an MSP....then on top of that staring multiple businesses that service MSPs (as the customer). ✅ The “New Game Plus” approach to starting businesses with accumulated experience. ✅ Why knowing your sweet spot—whether 0 to 1 million or 3 to 10 million—changes everything. ✅ The role of intentionality in aligning business with personal happiness. Dustin’s candid insights will leave you motivated to take the leap, refine your vision, and grow your business—on your terms. 🎧 Tune in here: Subscribe & listen in your favorite spot: -Youtube: youtu.be/aDjhMiR7dRY -Spotify: open.spotify.com/show/0NskmB… -Apple Podcasts: podcasts.apple.com/us/podcas… -Subscribe to new episodes: mspowner.com/ What’s your biggest challenge in growing your MSP? Let’s discuss below! 👇
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Episode 2 of the MSP Owner Podcast just dropped featuring the wonderful Dustin Bolander of Clear Guidance. Dustin and I met for breakfast 6 months ago, and I left thinking...wow that guy sure does a lot of things. 🎙️🚀 Dustin’s journey from a 12-year-old helping his family business to building and selling multiple MSPs is packed with lessons on leadership, growth, and making bold moves. Here’s what you’ll learn: ✅ Starting an MSP....then on top of that staring multiple businesses that service MSPs (as the customer). ✅ The “New Game Plus” approach to starting businesses with accumulated experience. ✅ Why knowing your sweet spot—whether 0 to 1 million or 3 to 10 million—changes everything. ✅ The role of intentionality in aligning business with personal happiness. Dustin’s candid insights will leave you motivated to take the leap, refine your vision, and grow your business—on your terms. 🎧 Tune in here: Subscribe & listen in your favorite spot: -Youtube: youtu.be/aDjhMiR7dRY -Spotify: open.spotify.com/show/0NskmB… -Apple Podcasts: podcasts.apple.com/us/podcas… -Subscribe to new episodes: mspowner.com/ What’s your biggest challenge in growing your MSP? Let’s discuss below! 👇
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The hedonic treadmill...Jacob Levine (who runs a $20M MSP) and I (owner of an $8M MSP) realized: we still don’t feel like we’ve nailed our niche In fact, it feels so far away in our minds that we're not sure we are ever going to get there. It’s a common theme among MSP & business owners—comparing ourselves to others who seem to be doing “cooler” or more focused things. We see others as having cracked the code, and us owners can’t help but think: Am I falling short? Should I be doing it that way too, or better? This constant push for more—for impact, for growth, for specialness in the eyes of our clients and employees—feels like a double-edged sword. On one hand, it drives progress and innovation. On the other, it feels like chasing a finish line that keeps moving further away. So that leads us to two key questions: Is this just the natural perspective of an owner—always looking ahead, striving for more, never feeling “done”? (hedonic treadmill) OR Does it come back to focus? Would dialing in on a clear, sharp niche actually unlock faster growth and a higher-quality business? Of course my entrepreneurial gut says it’s both. This is what we as owners wrestle with: it's who we are AND there's always a way to get better, do more. What’s your take? We talk about this and more on the latest episode of the MSP Owner Podcast. Check it out: mspowner.com
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Has anyone figured out a way to automate email follow-ups? Ex: ask a vendor a question. No response for 7 days. I have to manually remember to follow up (because most people don’t respond to initial emails for some reason). Anyway to solve or automate this big headache?
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🚀 MSP Owner Podcast has officially launched our first episode....LET's GO!!! 🎙️I want to welcome Jacob Levine of ROBO as the first guest, and it's a good one! MSP Owner is about the journeys of managed service provider (MSP) owners, exploring their challenges, successes, and lessons learned in the IT industry. Why should you care about the IT / MSP world (we're just a bunch of nerds, Right?)? Because it’s a goldmine of lessons about entrepreneurship, leadership, and innovation. The MSP industry is filled with owners who’ve navigated the complexities of scaling service businesses, solving high-stakes client problems, and adapting to rapidly evolving technology—all while building companies designed to provide consistent, reliable value. It's a tough business model that can drain you dry. I’ll uncover their founding stories & dig into how they grew their business from nothing into something. From scrappy beginnings to successful exits, these entrepreneurs have valuable insights to share. Whether it’s how they market their services, manage their teams, or differentiate themselves in a crowded marketplace, the takeaways are applicable far beyond the world of IT services. 💡 In this episode "Robo's Rise: Jake Levine on Building a $20 Million MSP", Jake Levine shares his remarkable journey from a non-technical background to leading a $20M MSP. He opens up about: -Acquiring two MSPs without any IT services background or experience -Navigating acquisitions with a focus on relationship-building. -Tackling keyman risk and client expectations post-acquisition. -Transitioning from founder-driven operations to a scalable structure. -His vision for the future of MSPs in a competitive industry. 🎧 Ready to tune in? Subscribe & listen in your favorite spot. Links in the first comment!! 👋 Please re-share & comment for reach! I welcome any and all feedback. Feedback is a gift and I promise to get & do better should you provide it. Let’s grow together! 🚀
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In EOS, there are 2 key leadership positions - the Visionary and Integrator. A visionary is going to come up with a lot of ideas and be poor on execution. While an integrator should be taking those GREAT ideas and making them into reality while telling the visionary no on the terrible and bad ideas. Magic ensues if this collab is present. What you don’t want to have (at least in business): a visionary who goes spouting off ideas to the entire team without context. This causes confusion, chaos, excitement, disjointed and unclear vision about where the team is going and what the priorities should be. I try to not do this (sometimes fail)… As a CEO, if I voiced every crazy idea that was in my head to my team before vetting it, it would be very bad……
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Exciting News** MSP Owner Podcast launches next week! I've spent countless hours the past 1.5 years since I acquired DataTel talking to hundreds of IT company owners. I've learned so much from these conversations and being open, authentic, and hearing other owner level experiences has 100% propelled my MSP to the next level...And I see huge value to the community in bringing these conversations to the public. This video podcast is for industry vets, it's for aspiring founders, it's for managers who want to buyout their existing owner, it's for people who like to hear stories. I believe the story matters more than the result. The journey is what is most interesting. How did you get here? What were those critical decision points? What sucked? What was amazing? Owners put pieces of themselves everyday as they make decisions to move their business forward. Managed Services is a massive industry that is highly fragmented. This means lots of people doing things different ways, lots of options for clients, and a big sales/marketing challenge. It's a people business (messy). It's also a rapidly evolving landscape with new challenges and opportunities everyday, especially relating to AI and cybersecurity. The better we do as an industry by sharing best practices, knowledge and the right ways of doing business, the better for clients, employees, management, and ownership across the board. How can you help?!? 1. Tag an MSP or an MSP owner you'd think would be good to have on the podcast 2. 5 Star/Review MSP Owner show on either Spotify or Apple Podcasts 3. Subscribe for new episodes at mspowner.com
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If you have the budget for an EOS implementor, pay for it and you’ll see better and faster results I’m a fan of if you’re doing something, do it the right way (all-in) But make sure you find the right ‘fit’ during your interview process with you and your team
For those who run EOS -- What is your one most important lesson learned?
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Had a great time with Patrick and Clint talking about a wide range of topics in a short amount of time. It’ll be clear if you listen…but I’m excited about where my MSP IT services business is at and the team that we have built. 2025 is about journey over destination.
New Inspired Or Acquired episode with Ben Tiggelaar is live. We discuss how he acquired an amazing IT services business, additional acquisitions, if he’d sell, and why he’s enjoying his career more now than ever. Full episode link in bio. @bentigg @ClintFiore
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Self-funded ‘step up’ has always been a very dumb descriptor…it was bastardized from traditional search investing where its intent was to step up pre-acquisition search capital to justify the increased risk of capital going in prior to a target being acquired New name is needed for sure ‘Equity factor’ is the best I’ve heard so far, but also needs serious work In fact, I think using the term ‘equity’ is a gross misnomer too. Self funded equity is much more similar to subordinated debt in terms of its structure and limited equity upside (warrants). It’s NOT equity other than in its name. Thoughts?? Any better naming ideas that accurately represent what it is??
To all "Self-Funded Search" stakeholders, stop calling it a "step-up". It's not a step-up, it's a step-down. When we use the term "step-up", it sounds like investors are getting an unfair deal. I assure you, we are not. Investors who put up 15% of the total deal value (but virtually 100% of the equity) and end up with only 25-30% of the common equity (a 1.7-2.0x "step-up") are not getting a "rich" or unfair deal at the expense of the searcher. The self-funded search deal is effectively a single asset private equity fund where the "self-funded" searcher is charging a large management fee (their salary) plus a 70-75% carry on all of the profits after a preferred return. In no other world would this be called a "step-up" or would a sponsor be able to put up virtually no equity and end up with a majority of the common equity (or carry) and have full control. And no, the SBA debt that you're PG-ing is not an equity contribution from you. 100% of the cash flows and proceeds from the sale of the business goes towards repaying that debt first. The investors are paying that debt off just as much as you. I recommend we start using the term "equity factor" as it better describes what it is. Investors who put up $1.5m of equity on a $10m deal (15% of EV), and receive 30% of the common equity, are receiving a 2x "equity factor" (not "step-up"). I've recently received a number of deals marketed with a 1.0-1.25x "step-up". I'm not sure who is advising these searchers, but this math simply does not work or make sense on a risk-adjusted basis. The problem is, due to a competitive deal market, and a desire to do a "big" deal, these searchers are paying up a bit (4-5x ) for larger businesses ($10-12m EV) and can only get $5-$7m of senior debt and $1-$2m of seller financing. They need $2.5-$3.0m of equity (25-30% of EV) to get the deal done but they don't want to give up the 35-45% of the common equity that is going to be required to make the deal work. They've read about other searchers getting 70-80% of the common equity and they want to get that too (and who doesn't, right?). Unfortunately, IMO, the math just doesn't make sense on a risk-adjusted basis and requires using very aggressive assumptions. The searchers that get 70-80% of the common are paying 3-4x and only need 10-15% of the deal value in equity.
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If you're using Chrome as your daily browser (and paying for Microsoft 365 licensing): you are doing it WRONG. Not only is Edge faster...the single best unique feature is that when you click a link from an email in Outlook, the Edge browser opens and there is a sidebar that shows you the original email so you have *context*. It has saved me so much back and forth, and annoyance with screen adjusting & shifting. One of the 500 reasons to fully utilize & adopt the entire Microsoft ecosystem. All you have to do to switch is import your favorites and apps from Chrome, then set your preferred browser to Edge. Get with the program people...this isn't 2019. Give it a try before you knock it.
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Lunching @MSP_Owner video podcast has been extremely fun...branding still in progress...Creating the strategy, setting up the tools & systems, doing initial recording sessions, figuring out how to position myself in the camera, training myself not to say 'um' so much. 4 pods completed, 5 more on the books, more requests coming already from MSP owners wanting to share their story. Each one is getting better. The best value for me personally so far: Every time I talk with another IT services company owner, I find multiple actionable things to improve myself, my team, and my company as CEO of DataTel. Thanks Brian Hoppe for some 'process' gold nuggets (8,000 pieces of documentation at his MSP)
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Get notified of the launch and first episodes here: forms.office.com/r/ye5qnTi4v…
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