M&A Zing (S2EP18) - Beyond “ABC”: The Art and Practice of Good SMB M&A with Andrew Longcore
Season 2, Episode 18, Nov 13, 10:18 AM
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Attorney-operator Andrew Longcore breaks down how to “defeat the unknown” in SMB deals: balancing people and paperwork, creative structures that share risk, avoiding seller remorse, and the first-year realities buyers ignore. Practical, people-first M&A without the hype. Chapters included.
This week Gareth is joined by Andrew Longcore - Managing Partner at Business Law Group and Founder of Cecil Sterling & Co. - to unpack what makes a good small-to-mid market deal and how to avoid the traps new acquirers fall into.
Andrew’s mission is simple: help entrepreneurs “defeat the unknown” in transactions. We get into buy-side vs sell-side realities, why many SMBs underuse acquisitions for growth, how to balance legal diligence with the human factors, and practical ways to structure deals so both sides win post-close.
Highlights include: creative risk-sharing beyond cookie-cutter terms, funding constraints for services businesses, handling seller remorse, assembling the right deal team, and why empathy is a competitive advantage in M&A. If you care about buying well and operating better, this is a sharp, no-fluff playbook from someone who’s seen hundreds of transactions.
[00:13] Intro to Andrew
[00:49] Founding Business Law Group → launching Cecil Sterling
[02:04] Why SMBs matter: community, jobs, and overlooked deals
[03:27] “Defeating the unknown” in transactions
[04:43] Diligence vs personalities: where the real risks hide
[05:37] Why SMB owners underuse M&A for growth
[06:38] Freedom, control and buying time via deals
[07:39] Don’t underthink post-close: vision before closing
[08:53] What “good deal” feels like (both sides win)
[10:11] Trust, remorse and structures that actually hold up
[11:47] US vs UK/EU risk appetites and financing realities
[12:40] People first, numbers second… but don’t skip the numbers
[13:58] Empathy as an M&A edge
[15:12] Paying for future performance without overpaying today
[16:14] New blood, influencer myths and real landmines
[17:51] Managing complexity, assembling the right deal team
[19:36] Building firms, loneliness of leadership, finding your “Yoda”
[21:07] Operating cadence and alignment (EOS)
[22:00] Goals for the next 12 months
[22:33] How to reach Andrew; closing takeaways
Show notes
Guest: Andrew Longcore
Managing Partner, Business Law Group:
https://www.businesslawgr.com/
Founder, Cecil Sterling & Co:
https://www.cecilsterling.com/
Focus: SMB buy-side and sell-side transactions, legal and advisory, post-close integration.
Topics: risk allocation, seller psychology, services-business funding, creative structures, deal team makeup, EOS after the acquisition.
Find Andrew on LinkedIn: / andrewlongcore
Host: Gareth Hawkins - CEO BizCrunch:
https://www.bizcrunch.co/
Andrew’s mission is simple: help entrepreneurs “defeat the unknown” in transactions. We get into buy-side vs sell-side realities, why many SMBs underuse acquisitions for growth, how to balance legal diligence with the human factors, and practical ways to structure deals so both sides win post-close.
Highlights include: creative risk-sharing beyond cookie-cutter terms, funding constraints for services businesses, handling seller remorse, assembling the right deal team, and why empathy is a competitive advantage in M&A. If you care about buying well and operating better, this is a sharp, no-fluff playbook from someone who’s seen hundreds of transactions.
[00:13] Intro to Andrew
[00:49] Founding Business Law Group → launching Cecil Sterling
[02:04] Why SMBs matter: community, jobs, and overlooked deals
[03:27] “Defeating the unknown” in transactions
[04:43] Diligence vs personalities: where the real risks hide
[05:37] Why SMB owners underuse M&A for growth
[06:38] Freedom, control and buying time via deals
[07:39] Don’t underthink post-close: vision before closing
[08:53] What “good deal” feels like (both sides win)
[10:11] Trust, remorse and structures that actually hold up
[11:47] US vs UK/EU risk appetites and financing realities
[12:40] People first, numbers second… but don’t skip the numbers
[13:58] Empathy as an M&A edge
[15:12] Paying for future performance without overpaying today
[16:14] New blood, influencer myths and real landmines
[17:51] Managing complexity, assembling the right deal team
[19:36] Building firms, loneliness of leadership, finding your “Yoda”
[21:07] Operating cadence and alignment (EOS)
[22:00] Goals for the next 12 months
[22:33] How to reach Andrew; closing takeaways
Show notes
Guest: Andrew Longcore
Managing Partner, Business Law Group:
https://www.businesslawgr.com/
Founder, Cecil Sterling & Co:
https://www.cecilsterling.com/
Focus: SMB buy-side and sell-side transactions, legal and advisory, post-close integration.
Topics: risk allocation, seller psychology, services-business funding, creative structures, deal team makeup, EOS after the acquisition.
Find Andrew on LinkedIn: / andrewlongcore
Host: Gareth Hawkins - CEO BizCrunch:
https://www.bizcrunch.co/