The only podcast dedicated exclusively to Entrepreneurs and CEOs running Small to Medium Sized Businesses (SMB). Nobody knows what it’s like to be an Entrepreneur or CEO unless you’ve been one. Though many understand the rewards of company leadership, very few understand the arduous journey that’s required to get (and stay) there. I share my own lessons as an Entrepreneur and CEO, and interview experts spanning Sales, Leadership, Mental Health, M&A, and Operations (among others) all with a s ...
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Evaluating The Most Common Forms of Debt Used to Finance Small Business Acquisitions
27:52
27:52
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This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses * This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and O…
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From $7M to $50M via 14 Acquisitions: A Consolidation Success Story With Jay Davis & Jason Pananos
1:26:04
1:26:04
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1:26:04
This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses *This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Sm…
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Why You May Be Ignoring Brokered Deals at Your Peril
1:06:32
1:06:32
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1:06:32
This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses * This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Othe…
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Why You May Want to Reconsider Your Industry Roll-up Strategy
19:53
19:53
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19:53
This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses *This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small…
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This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses * This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and …
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The Constellation Software Playbook for Acquiring and Growing Software Companies
1:17:56
1:17:56
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This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses * This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medi…
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Evaluating Stock Options as Attraction, Retention, and Incentive Alignment Tools
22:55
22:55
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22:55
This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses * This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Si…
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Can Ambition and Inner Peace Coexist? With Rob Dube
1:26:38
1:26:38
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1:26:38
This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses * This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-…
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Answers to Recurring FAQs from Current and Prospective Searchers
44:57
44:57
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This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses * This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized…
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Profit Before Anything Else: With Mike Michalowicz, Author of "Profit First"
1:19:11
1:19:11
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1:19:11
This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses * This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium…
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Royce Yudkoff & Rick Ruback: Educators, Mentors, and Leaders Within the SMB Community
1:02:18
1:02:18
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1:02:18
This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses * This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Siz…
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Jeff Stevens & A.J. Wasserstein on The Future of Entrepreneurship Through Acquisition
1:32:44
1:32:44
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1:32:44
This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses * This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Bu…
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Michael Girdley on The Rise of Holding Companies
57:07
57:07
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This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses * This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Busine…
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Questions You Should Be Prepared to Answer Before Buying (or Selling) a Small Business
29:05
29:05
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29:05
This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses * This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses…
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What I'd Change if I Could Re-Do the First 90 Days of my Search: 3 Searcher Case Studies
1:00:32
1:00:32
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1:00:32
This episode is brought to you by The Profit Line: The Outsourced Finance & Accounting Department for Small and Medium Sized Businesses * This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses * In…
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Dr. Victoria Medvec on the Art and Science of High Stakes Negotiations
1:35:24
1:35:24
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1:35:24
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,…
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Peter Lehrman, Founder & CEO of Axial, The Largest Online Marketplace to Buy & Sell SMBs
1:24:16
1:24:16
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1:24:16
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 …
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Conscious Leadership with Executive Coach and Best-Selling Author Kaley Klemp
57:49
57:49
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57:49
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, U…
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Building a $5.5B Mid-Market Private Equity Firm: Brent Belzberg, Founder of Torquest Partners
1:16:24
1:16:24
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1:16:24
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…
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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 …
…
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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 decad…
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This episode is brought to you by Symphony. On September 8th, 2023, Symphony will be live-streaming a webinar on searchfunder.com all about the technical due diligence process when acquiring a software company. Use this link to sign up: https://www.searchfunder.com/event/view/1200. Symphony not only performs technical due dili…
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"A Guide to the Good Life": What Entrepreneurs Can Learn From Stoic Philosophy
1:19:49
1:19:49
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1:19:49
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 no…
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Venture Capital “Orphans”: Exploring an Emerging Search Fund Investment Thesis
17:00
17:00
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17:00
This episode is brought to you by Symphony. On September 8th, 2023, Symphony will be live-streaming a webinar on searchfunder.com all about the technical due diligence process when acquiring a software company. Use this link to sign up: https://www.searchfunder.com/event/view/1200. Symphony not only performs technical due diligenc…
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When Search Funds Don’t Go As Planned (Part 2): With Jim Sharpe
1:02:56
1:02:56
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1:02:56
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 refres…
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Lessons Learned From 400+ Post-Exit Entrepreneurs: John Warrillow, Host of Built to Sell Radio
53:43
53:43
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53:43
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…
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When Search Funds Don't Go As Planned (Part 1): 3 Searcher Case Studies
1:54:02
1:54:02
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1:54:02
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 du…
…
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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, Q…
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The SMB Credit Markets: Bank Failures, Rising Interest Rates, and a Looming Recession
1:09:36
1:09:36
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1:09:36
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 …
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The Merits, Risks, and Possible Unintended Consequences of Earn-Outs
23:10
23:10
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23:10
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 prof…
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Mental Health for High Achievers: Ambition, Anxiety, Perfectionism, and Balancing Striving vs. Self-Acceptance
1:34:48
1:34:48
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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 profes…
…
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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, communicati…
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Kent Weaver: Building, Working With, and Learning from your Board of Directors
55:25
55:25
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55:25
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,…
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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…
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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 w…
…
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Everything You've Ever Wanted to Know About Working with a Partner: With Dr. Noam Wasserman, Author of The Founder's Dilemmas
1:37:54
1:37:54
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1:37:54
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,…
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Evaluating the Correlation Between Hours Worked and Success Achieved
14:38
14:38
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14:38
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,…
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The Smallest Changes That Had The Largest Impacts: 4 CEO Case Studies
1:30:28
1:30:28
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1:30:28
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,…
…
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Constructing, Managing, and Working with a Board of Directors
21:30
21:30
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21:30
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…
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Mike Zani, CEO of The Predictive Index: Hiring, Personality Profiling Tools, Working with a Partner, and Other Lessons from 20 Years as a CEO
1:30:52
1:30:52
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1:30:52
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…
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1
The Current State of the Debt Capital Markets
59:39
59:39
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59:39
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 to the best extent possible, I want to prevent others from making the same…
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Evaluating 5 Very Different Approaches to Acquiring a Software Company
30:36
30:36
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30:36
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 to the best extent possible, I want to prevent others from making the same…
…
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1
Brent Beshore: The "Forrest Gump of Private Equity"
1:27:10
1:27:10
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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. I have personally read though, analyzed, and relied upon several of their actual QofE reports in my capacity as an SMB investor, and can personally attest …
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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. I have personally read though, analyzed, and relied upon several of their actual QofE reports in my capacity as an SMB investor, and can personally attest …
…
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A.J. Wasserstein: Reflections of a Founder, CEO, Investor and Educator
1:13:42
1:13:42
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1:13:42
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. I have personally read though, analyzed, and relied upon several of their actual QofE reports in my capacity as an SMB investor, and can personally attest …
…
continue reading
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. I have personally read though, analyzed, and relied upon several of their actual QofE reports in my capacity as an SMB investor, and can personally attest …
…
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Buy at 5X EBITDA, Sell at 8X Revenue: The On-Premise to SaaS Transition of FieldEdge
1:18:50
1:18:50
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My guests today are Steve Lau and Rameez Ansari, co-CEOs of AutoLeap, a software company that services auto repair shops, that counts Bain Capital Ventures among its investors. Prior to founding AutoLeap, Steve and Rameez purchased, operated, and sold D'Esco (later renamed FieldEdge), a software company that helps entrepreneurs run their HVAC, Plum…
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Unfortunate at this reality may be, I would argue that firing (specifically knowing who, when, and how to fire) is a required core competency for any CEO, and is arguably as important as hiring, communication, capital allocation, and other tools within the CEO’s toolkit. The extent to which this is an unpleasant (and perhaps even unpopular) topic t…
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Sell-Side M&A Advisors: How to Choose One, How Much They Cost, and The Importance of the "Fine Print"
1:07:26
1:07:26
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Today’s episode is for anybody who ever plans to sell a company. Most entrepreneurs will sell a business once in their entire careers (if they’re lucky), and as a result many understandably don’t have a lot of context or experience in the finer points of exiting, specifically when it comes to how to select an M&A advisor. Most advice that I’ve come…
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Strategic Considerations When Evaluating a Letter of Intent to Sell Your Business
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15:32
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For many business owners, few things are as exciting as receiving a Letter of Intent (“LOI”) from a prospective purchaser. Beyond the sense of validation stemming from the fact that a sophisticated counterparty sees an asset worth paying for, many business owners likely view an LOI as a just reward for decades of hard work, sacrifice, and illiquidi…
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