BUILT with Otavio Pailo

If you lead an established service business and an operating bottleneck is limiting profitable growth, start with a Free Expert Assessment. Get a written recommendation on the likely constraint and the next step: https://alreadybuilt.ai/strategy?r=e009p&utm_source=podcast&utm_medium=description&utm_campaign=E009-joseph-strazzeri&utm_content=desc_top Joe Strazzeri is a California attorney and the co-founder of Strazzeri Mancini LLP in San Diego. He works on tax, estate and succession planning for business owners and their families. Before law, he was a general contractor and land developer who built and sold two companies. He explains why many owners back out of a sale at the last minute, why tax planning has to start long before the letter of intent, and why the sale multiple matters more than EBITDA. This is general education, not tax or legal advice for your situation. We also cover California residency and taxes when you sell, QSBS stacking, C corp versus S corp for a company built to sell, why advisors earn more when clients pay more tax, life after the sale, and why owners keep too much of their net worth in the business. Where to find Joe Strazzeri: Care to Know: https://caretoknow.info Strazzeri Mancini: https://strazzerimancini.com The Founders Group: https://foundersgroup.biz Southern California Institute: https://scinstitute.org LinkedIn: https://www.linkedin.com/in/joestrazzeri/ In this episode: 00:00 You're not going to sell 00:13 From contractor to tax attorney 05:00 Out-of-state trusts 07:36 How much California tax costs you 09:34 Taxes, jobs and the state budget 10:55 Selling a business in California 13:38 Moving before a sale 15:29 How long you must be gone 18:32 Why delay the tax 20:02 Advisor incentives 21:59 C corp or S corp? 23:43 QSBS stacking 25:04 Plan before the LOI 26:11 The multiple beats EBITDA 27:09 You're not going to sell: the math 28:13 Life after the sale 31:35 Retirement is a slope 35:48 Owners are misunderstood 37:12 Take chips off the table 38:53 Too much net worth in the business 40:02 AI and mundane billable work 40:36 Where to find Joe Referenced: Motive, by Joe Strazzeri: https://caretoknow.info/motive/ Younger Next Year, by Chris Crowley and Henry S. Lodge Dan Sullivan's Strategic Coach More Value: Learn the tactics my team and I are using as we scale to delivering $1B+ in client value: https://alreadybuilt.ai/brief?r=e009b&utm_source=podcast&utm_medium=description&utm_campaign=E009-joseph-strazzeri&utm_content=desc_bottom Watch my latest YouTube videos: https://www.youtube.com/@OtavioPailo DISCLOSURE: Information shared here is for educational purposes only. Individuals and business owners should evaluate their own business strategies and identify any potential risks. The information shared here is not a guarantee of success. Your results may vary. Copyright © 2026.

If you're a $3M+ business in a regulated industry, we'll find the #1 constraint bottlenecking your business and the best solution to solve it - whether it's AI or not - for free: https://alreadybuilt.ai/strategy?r=e010p&utm_source=podcast&utm_medium=description&utm_campaign=E010-henning-schwinum&utm_content=desc_top "Guess what's the common denominator between the 10? It's the leadership." Henning Schwinum is Co-Founder and Managing Partner of Vendux, which matches companies with fractional and interim sales leaders, and Executive Director of the Fractional Leadership Alliance. He spent 15 years at Bayer, then helped build a nine-person startup into an international business that Underwriters Laboratories acquired. His book is Right-Sized, Right-Skilled. He joins Otavio Pailo to explain how an owner can tell that the company has outgrown its sales leadership, when a fractional sales leader is the right answer and when a full-time hire is, and why the fractional industry has struggled to prove what it delivers. We discuss the player-coach trap, getting out of founder-led sales, where the fractional model stops working, why 'ex-Google' and job titles tell you little, the founder who will not let a new leader change anything, planning the end of an engagement in week one, playbooks versus superstars, and measuring a fractional against the goals in the statement of work. Where to find Henning Schwinum: Vendux: https://www.vendux.org Fractional Leadership Alliance: https://www.fractionalleadershipalliance.com Right-Sized, Right-Skilled (his book): https://www.vendux.org/rightsized-rightskilled LinkedIn: https://www.linkedin.com/in/henning-schwinum/ In this episode: 00:00 Hired and fired 10 sales reps? It's the leadership 00:19 Meet Henning Schwinum 01:40 From Bayer to a nine-person startup 03:27 What the startup taught him: customer centricity 05:16 Vendux works for the client, not the executive 06:20 Why a niche firm builds proof, not a brand 09:59 Why sales, and the name Vendux 12:34 Is your business outgrowing its sales leadership? 15:04 The player-coach trap 17:04 Getting out of founder-led sales 19:49 A consultant tells you. A fractional fixes it. 20:44 Where fractional stops working 23:15 How Vendux matches an executive to a company 26:46 AI in matching, and 'did you really close Wells Fargo?' 28:39 Why 'ex-Google' and titles mean nothing 30:37 When the founder does not know what good looks like 33:01 Who are you to tell me my baby is ugly? 35:31 When the founder is the one not listening 38:02 Plan the end of the engagement in week one 40:48 Playbooks vs superstars 44:46 Why some founders stay stuck 47:29 Bring in a CEO who has scaled before 49:29 Proving a fractional executive paid off 52:50 Hard OpEx vs 'what-if' ROI 55:09 Measure the goals in the statement of work 56:13 The belief his peers argue with 57:26 Where to find Henning More Value: Learn the tactics my team and I are using as we scale to delivering $1B+ in client value: https://alreadybuilt.ai/brief?r=e010b&utm_source=podcast&utm_medium=description&utm_campaign=E010-henning-schwinum&utm_content=desc_bottom Watch my latest YouTube videos: https://www.youtube.com/@OtavioPailo DISCLOSURE: Information shared here is for educational purposes only. Individuals and business owners should evaluate their own business strategies and identify any potential risks. The information shared here is not a guarantee of success. Your results may vary. Copyright © 2026.

If you're a $3M+ business in a regulated industry, we'll find the #1 constraint bottlenecking your business and the best solution to solve it - whether it's AI or not - for free: https://alreadybuilt.ai/strategy?r=e001p&utm_source=podcast&utm_medium=description&utm_campaign=E001-michael-magliochetti&utm_content=desc_top "What you have to understand as a seller is what is life going to be like day one post-investment, day 100, day 1,000." Michael Magliochetti was CEO of four venture- and PE-backed healthcare companies and led three of them through successful sales, including Claros Diagnostics to OPKO Health for $49 million. Since 2012 he has been an Operating Partner at RS2 Healthcare Partners (formerly Riverside Partners), where he chairs the healthcare advisory board. He joins Otavio Pailo to explain what a seller should check before choosing a private equity buyer, what changes after the deal closes, and why his firm passes on most of the 200-plus companies it reviews each year. We discuss the seller's side of a sale, the first hire he makes after a deal, why RS2 built clinical and AI advisory boards, where AI is paying off across a healthcare portfolio, the deal behind the title of his book Dancing Between the Toes of Elephants, and why private equity runs on transparency and trust. Where to find Michael Magliochetti: LinkedIn: https://www.linkedin.com/in/michael-magliochetti-9905371/ RS2 Healthcare Partners: https://rs2healthcare.com/ His book, Dancing Between the Toes of Elephants: https://www.amazon.com/Dancing-Between-Toes-Elephants-Experience/dp/1964421136 Michael welcomes founders of pharma services, medical device and tech-enabled healthcare services companies, even if a sale is two or three years away. In this episode: 00:00 Cold open: a marriage you can't get out of 00:20 Michael Magliochetti: four CEO seats, three exits, now the buyer 01:30 What RS2 Healthcare looks for in a company 05:14 The seller's chair: a buyer is like someone marrying your daughter 07:23 From PhD scientist to CEO: being bilingual 11:24 The founder-scientist's blind spot: go-to-market 13:44 You can teach a scientist business, not the other way around 15:51 The first hire after the deal: a professional CFO 17:13 What a PE firm brings after the deal 20:13 Shop for the partner, not the biggest check 21:40 Life on day one, day 100 and day 1,000 23:49 How sellers slow a deal and lose credibility 24:51 Why RS2 built clinical and AI advisory boards 26:38 The AI summit with the portfolio's technology leaders 28:17 Stop swinging for the fences with AI 30:27 Start with the one part of the workflow that matters 32:29 AI in pharma services and drug discovery 35:12 The book: from a private journal to a #1 bestseller 40:57 The deal he voted no on 46:15 Deal fever and dancing between the toes of elephants 49:21 What drives a pass: 200 companies, two or three investments 51:42 Where PE creates value: people, go-to-market, then add-ons 54:34 KMM Group: the team was ready on closing day 57:05 The contrarian belief: PE runs on transparency and trust 61:47 Where to find Michael Referenced: Dancing Between the Toes of Elephants by Michael Magliochetti: https://www.amazon.com/Dancing-Between-Toes-Elephants-Experience/dp/1964421136 More Value: Learn the tactics my team and I are using as we scale to delivering $1B+ in client value: https://alreadybuilt.ai/brief?r=e001b&utm_source=podcast&utm_medium=description&utm_campaign=E001-michael-magliochetti&utm_content=desc_bottom Watch my latest YouTube videos: https://www.youtube.com/@otavio_pailo DISCLOSURE: Information shared here is for educational purposes only. Individuals and business owners should evaluate their own business strategies and identify any potential risks. The information shared here is not a guarantee of success. Your results may vary. Copyright © 2026.

If you're a $3M+ business in a regulated industry, we'll find the #1 constraint bottlenecking your business and the best solution to solve it - whether it's AI or not - for free: https://alreadybuilt.ai/strategy?r=e008p&utm_source=podcast&utm_medium=description&utm_campaign=E008-michael-stier&utm_content=desc_top "You basically built yourself a very demanding job. You haven't built a business of value." Michael Stier founded Adhesion Wealth, ran it for 18 years and sold it in 2018. Today he is Area President at FocusCFO for the Carolinas, a Certified Exit Planning Advisor, and he leads the Exit Planning Exchange chapter in Charlotte. He joins Otavio Pailo to explain why a business that cannot run without its owner has little value to a buyer, what messy books tell a buyer before any meeting, and how to get a company ready long before an offer arrives. We discuss why so many founders regret their exit, the owner who panics before closing, the earn-out trap, why growth hits walls, how far back to clean up the books, where AI helps with the numbers, the six-week vacation test, the CFO as chief de-risking officer, fractional versus full-time CFOs, and why he measures cash flow instead of revenue. Where to find Michael Stier: FocusCFO: https://www.focuscfo.com/fractional-cfo-team/michael-stier LinkedIn: https://www.linkedin.com/in/michaelstier/ Michael works with founder-led companies of roughly $5M to $50M in revenue, and with the bankers, wealth advisors and coaches who serve them. In this episode: 00:00 A business that can't run without you 00:14 Meet Michael Stier 01:23 Why he sold Adhesion after 18 years 03:46 The last walk out of the office 05:56 When owners panic before closing 06:27 Why founders regret the exit 08:51 Start exit planning years early 11:04 Fix it and you may not want to sell 13:41 People, systems and key-man risk 15:28 The earn-out trap 19:49 Founders who build themselves a job 21:53 Growth hits walls 24:15 Profitable is not sellable 26:40 What buyers see in messy books 30:36 Personal expenses and lender scrutiny 32:24 How far back to clean the books 33:41 Where AI helps with the numbers 35:50 Be ready before the offer comes 37:57 The six-week vacation test 40:40 The CFO as chief de-risking officer 42:25 Fractional vs. full-time CFO 45:21 AI, capital and the department of no 48:07 Measure cash flow, not revenue 50:39 Why an outside CFO tells you the truth 52:48 His filter: are they coachable? 56:21 Where to find Michael Referenced: Built to Sell by John Warrillow EOS, the Entrepreneurial Operating System More Value: Learn the tactics my team and I are using as we scale to delivering $1B+ in client value: https://alreadybuilt.ai/brief?r=e008b&utm_source=podcast&utm_medium=description&utm_campaign=E008-michael-stier&utm_content=desc_bottom Watch my latest YouTube videos: https://www.youtube.com/@otavio_pailo DISCLOSURE: Information shared here is for educational purposes only. Individuals and business owners should evaluate their own business strategies and identify any potential risks. The information shared here is not a guarantee of success. Your results may vary. Copyright © 2026.

If you're a $3M+ business in a regulated industry, we'll find the #1 constraint bottlenecking your business and the best solution to solve it - whether it's AI or not - for free: https://alreadybuilt.ai/strategy?r=e006p&utm_source=podcast&utm_medium=description&utm_campaign=E006-marco-villarreal&utm_content=desc_top Marco Villarreal has seen finance at scale: a BPO company grew from 1,500 to 17,000 people and closed seven acquisitions while he was CFO. Now he works with owner-led businesses as a fractional CFO at The CFO Centre. Marco explains why a smooth AI answer should make a finance leader ask harder questions. He walks through his own three-day AI modeling process, the prompts he uses to challenge assumptions, and why every number must trace back to its source. We also discuss cash-flow reporting, acquisition diligence, and how to test an AI finance tool before buying it. Where to find Marco Villarreal: Marco’s CFO Centre profile: https://www.cfocentre.com/us/meet-the-cfos/marco-villarreal-fractional-cfo/ The CFO Centre: https://www.cfocentre.com/us/ LinkedIn: https://www.linkedin.com/in/marcoavillarreal References mentioned: Advait Sarkar's TED talk on AI and critical thinking: https://www.ted.com/talks/advait_sarkar_how_to_stop_ai_from_killing_your_critical_thinking Reshuffle by Sangeet Paul Choudary: https://notionpress.com/in/read/reshuffle-hardcover In this episode: 00:00 Why smooth AI work should worry you 00:14 Meet Marco Villarreal 01:18 From engineering to finance 05:05 The fractional CFO model 07:34 What breaks when a company grows 15:29 The 13-week cash-flow view 18:09 Diligence beyond the numbers 22:31 Marco's first AI finance model 27:09 Make AI challenge your plan 30:52 Traceable numbers and the accountant 32:53 Which model fits the job 35:15 How to test an AI finance tool 38:05 Start with the real business problem 49:30 Ask the incumbent team what it tried 56:46 Who needs a strategic CFO More Value: Learn the tactics my team and I are using as we scale to delivering $1B+ in client value: https://alreadybuilt.ai/brief?r=e006b&utm_source=podcast&utm_medium=description&utm_campaign=E006-marco-villarreal&utm_content=desc_bottom Watch my latest YouTube videos: https://www.youtube.com/@otavio_pailo DISCLOSURE: Information shared here is for educational purposes only. Individuals and business owners should evaluate their own business strategies and identify any potential risks. The information shared here is not a guarantee of success. Your results may vary. Copyright © 2026.