In The Trenches
The Only Podcast Dedicated Exclusively to Entrepreneurs and CEOs Running Small and Medium Sized Businesses
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anxiety burnout buying a business CEO time and emotion communication compensation structure core values culture customers deal terms depression disruption financing focus goal setting growth hiring HR imposter syndrome incentives liquidity LOIs M&A M&A advisor management team meditation mental health metrics perfectionism pricing product management profitability SaaS salaries sales compensation self care selling a business software spouses and partners stoicism strategy technical debt time management transparency valuation
BUYING A BUSINESS
Quality of Earnings Analysis: What You Need to Know Before Buying a Business
My Guest My guest today is Chris Hutchinson, a Partner in Ernst & Young’s Transaction Advisory Services Group. Chris has over 15 years of experience advising clients on M&A, financings, valuation projects, and due diligence mandates, with a specific focus on private lower-middle-market businesses. Chris and his team have completed an untold number of QualityContinue reading “Quality of Earnings Analysis: What You Need to Know Before Buying a Business”
MANAGING YOURSELF
Employee Burnout and The Great Resignation
My Guest My guest today is Carin-Isabel Knoop, Executive Director of the Harvard Business School Case Research & Writing Group. Carin has spent decades writing cases on managers and leaders all over the world across a wide array of functions and industries. In 2019, alongside co-author John Quelch, Carin published Compassionate Management of Mental HealthContinue reading “Employee Burnout and The Great Resignation”
Understanding and Managing The Psychological Toll of Being an Entrepreneur or CEO
My Guest Dr. Eliana Cohen is an entrepreneur and Clinical Psychologist who runs her own practice, integrating performance psychology, strategy, emotional intelligence, and knowledge of neuroplasticity and the brain to serve her various clients. She has worked with countless entrepreneurs, business owners, and CEOs in her practice, and is passionate about discussing the psychological realitiesContinue reading “Understanding and Managing The Psychological Toll of Being an Entrepreneur or CEO”
CEO Coaches: What do they do, how do they work with CEOs, and why might you consider hiring one?
My Guest Warren Coughlin is both an entrepreneur and business coach, having worked directly with countless Entrepreneurs and CEOs for upwards of 20 years. His coaching practice focuses not only on the business itself, but also on the entrepreneur at a personal level, working with them to ensure that they craft meaningful values and liveContinue reading “CEO Coaches: What do they do, how do they work with CEOs, and why might you consider hiring one?”
MANAGING YOUR BUSINESS
All Things Finance & Accounting: Managing Liquidity, Employee Financial Literacy, Capital Allocation, Macroeconomic Uncertainty, and Hiring Your First CFO
My Guest Nicholas Andrews is the Founder of Aspen Consulting Group, a company that performs finance, accounting, and operations consulting for a wide range of small and medium sized businesses. Aspen’s services include technical accounting, corporate finance, valuations, operations planning and M&A due diligence, among others. Prior to founding the Aspen Consulting group, Nick wasContinue reading “All Things Finance & Accounting: Managing Liquidity, Employee Financial Literacy, Capital Allocation, Macroeconomic Uncertainty, and Hiring Your First CFO”
Managing a Business During Inflationary Periods & Understanding Pricing Power
My Guest My guest today is a particularly personal and a particularly special one for me: I have been fortunate to call Jim Sharpe a mentor and friend for over 10 years now, and I am thrilled that he agreed to join the podcast. In this week’s episode, we discuss the realities of running aContinue reading “Managing a Business During Inflationary Periods & Understanding Pricing Power”
Having Hard Conversations (Live Panel Discussion from 2022 MIT Sloan Search Fund Summit)
In this week’s episode, we discuss the importance of having difficult conversations, something that CEOs find themselves doing on a near-daily basis. We discuss three primary types of difficult conversations, including: Hard conversations around internal company dynamics (eg: terminations); Hard conversations about dynamics external to the company (eg: politics and global affairs); Difficult conversations thatContinue reading “Having Hard Conversations (Live Panel Discussion from 2022 MIT Sloan Search Fund Summit)”
Aaron Ross: Author of “Predictable Revenue” and “From Impossible to Inevitable”
My Guest Though Aaron Ross wears many hats, he is perhaps best known for co-authoring the global best seller Predictable Revenue, often referred to as “The Sales Bible of Silicon Valley,” which details an outbound prospecting system that’s created more than $1 billion across Salesforce.com and other companies. Most recently, Aaron published From Impossible toContinue reading “Aaron Ross: Author of “Predictable Revenue” and “From Impossible to Inevitable””
Bob Pritchett: Author of “Fire Someone Today” and Founder & Executive Chairman of Faithlife Software
My Guest Bob Pritchett is a lifetime entrepreneur and CEO, having founded Logos Research Systems (later Logos Bible Software and now Faithlife) in 1992, and acting as its CEO for 30 years until recently assuming the role of Executive Chairman. During Bob’s tenure, Faithlife has grown both organically and inorganically from 2 employees to overContinue reading “Bob Pritchett: Author of “Fire Someone Today” and Founder & Executive Chairman of Faithlife Software”
All Things Hiring with Randy Street: Co-Author of “Who: The A-Method for Hiring” and Vice Chairman of ghSMART
My Guest Randy Street is Vice Chairman of ghSMART, a leading global consulting firm that helps CEOs, boards, and investors build valuable companies through hiring and developing world class leadership teams. During Randy’s tenure, ghSMART has grown tenfold, and has been ranked by Forbes as one of America’s Best Consulting Firms from 2017-2020. In collaborationContinue reading “All Things Hiring with Randy Street: Co-Author of “Who: The A-Method for Hiring” and Vice Chairman of ghSMART”
Verne Harnish: Founder of The Entrepreneurs’ Organization (EO), Author of “Scaling Up” and “Mastering the Rockefeller Habits”
My Guest Few people have done more for Entrepreneurs and CEOs than Verne Harnish: Verne is the founder of the world-renowned Entrepreneurs’ Organization (“EO”), a global network of entrepreneurs and CEOs that boasts over 16,000 members worldwide. For the past 15 years, Verne has chaired EO’s premiere CEO program, the “Birthing of Giants” held atContinue reading “Verne Harnish: Founder of The Entrepreneurs’ Organization (EO), Author of “Scaling Up” and “Mastering the Rockefeller Habits””
The Realities of Managing Extremely Rapid Growth
My Guest Anthemos Georgiades (or Anth, for short), is the founder and CEO of Zumper, an apartment rental platform based out of San Francisco that he founded in his second year at Harvard Business School in 2012. If anybody knows anything about running a rapidly growing company, it’s Anth. Consider this: Despite being founded lessContinue reading “The Realities of Managing Extremely Rapid Growth”
Rich Manders: Lessons from Founding, Growing, Buying, Selling, Coaching, and Investing in SMBs
My Guest Rich Manders Co-Founded and led iAutomation, a Massachusetts-based machine control and automation company, and grew the business from $0 to $90M in sales with 180 employees. After selling that business to The Riverside Company (a leading global Private Equity firm), Rich stayed on with the business, and alongside his partners at Riverside, grewContinue reading “Rich Manders: Lessons from Founding, Growing, Buying, Selling, Coaching, and Investing in SMBs”
Sales: Hiring, Onboarding, Compensating, Scaling & Supporting a World Class Sales Team
My Guest Dave Prusinksi is the Chief Revenue Officer at SafeAI, a hyper-growth silicon valley company in the autonomous vehicle space. Prior to his current role, Dave spent 10 years as the Executive Vice President of Sales and Marketing at FleetComplete, a technology provider to fleet-owning businesses around the world. Under Dave’s leadership, FleetComplete grewContinue reading “Sales: Hiring, Onboarding, Compensating, Scaling & Supporting a World Class Sales Team”
MANAGING YOUR BUSINESS (SOFTWARE-SPECIFIC)
Buy at 5X EBITDA, Sell at 8X Revenue: The On-Premise to SaaS Transition of FieldEdge
My Guests My guests today are Steve Lau and Rameez Ansari, co-CEOs of AutoLeap, a cloud-based auto repair shop platform 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, Plumbing, and ElectricalContinue reading “Buy at 5X EBITDA, Sell at 8X Revenue: The On-Premise to SaaS Transition of FieldEdge”
Building and Managing a World Class Product Management Discipline
My Guest Rich Mironov is one of North America’s preeminent Product Management thought leaders. He has spent 40 years in the software industry in numerous capacities, and currently acts as a Coach, Consultant, and Interim Executive for CEOs and Heads of Product across Canada and the United States, advising them on a diverse range ofContinue reading “Building and Managing a World Class Product Management Discipline”
The Private Equity Perspective on Acquiring, Operating and Selling Software Companies
My Guest Jordan Bettman is a Partner and Co-founder of Radian Capital, a New York-based Private Equity firm focused on B2B software and technology-enabled services businesses. Radian has ~$500 million of assets under management, and is now investing out of their second fund of ~$315 million. Prior to co-founding Radian, Jordan was a Partner atContinue reading “The Private Equity Perspective on Acquiring, Operating and Selling Software Companies”
SELLING YOUR BUSINESS
Sell-Side M&A Advisors: How to Choose One, How Much They Cost, and The Importance of the “Fine Print”
My Guest John Carvalho is the President of Stone Oak Capital, an M&A advisory firm that focuses exclusively on middle market businesses, with a specific focus on transactions between $10 and $100 million. Among other things, Stone Oak offers acquisition, divestitures, corporate finance and valuations services for its clients. John is also the Founder ofContinue reading “Sell-Side M&A Advisors: How to Choose One, How Much They Cost, and The Importance of the “Fine Print””
What M&A Lawyers Want CEOs to Know About Selling Their Companies
My Guest Mario Nigro is one of Canada’s preeminent M&A lawyers, and currently serves as a Partner in the Mergers & Acquisitions and Private Equity & Venture Capital Groups at Stikeman Elliot based out of Toronto. His practice focuses on mergers and acquisitions, financings, complex corporate reorganizations, and general business law. Mario has extensive experienceContinue reading “What M&A Lawyers Want CEOs to Know About Selling Their Companies”