In The Trenches


The Only Podcast Dedicated Exclusively to Entrepreneurs and CEOs Running Small and Medium Sized Businesses

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BUYING A BUSINESS

Peter Lehrman, Founder & CEO of Axial, The Largest Online Marketplace to Buy & Sell SMBs

My Guest Peter Lehrman is the Founder and CEO of Axial, North America’s #1 online platform connecting buyers and sellers of small and medium sized businesses. Axial is used by over 20,000 investors, M&A advisors and CEOs, allowing them to connect on a confidential basis to explore potential M&A, debt, buyout, and growth equity transactions,…

The Current State of the Debt Capital Markets

My Guests My guests today are Cory Kaiser and Timothy Eaton, Vice President & Associate Vice President respectively within TD’s Commercial Banking Group. Between them, they have over 40 years of experience lending to lower-middle market businesses not just to finance their acquisitions, but also to finance growth initiatives, day-to-day working capital needs, and leveraged…

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 Quality…


MANAGING YOURSELF

Conscious Leadership with Executive Coach and Best-Selling Author Kaley Klemp

My Guest Kaley Klemp is a highly sought after CEO coach, YPO forum facilitator, and best-selling author. In 2015, Kaley co-authored The 15 Commitments of Conscious Leadership, a book that was met with instant critical and commercial success, and followed that up in 2021 with The 80/80 Marriage, a book about how to strengthen and…

“A Guide to the Good Life”: What Entrepreneurs Can Learn From Stoic Philosophy

My Guest My guest today is Dr. William Irvine, author of the best-selling book A Guide to the Good Life: The Ancient Art of Stoic Joy. He is the author of several other books, including The Stoic Challenge, On Desire, and You: A Natural History (among others). Dr. Irvine’s work has been featured in countless…

When Search Funds Don’t Go As Planned (Part 1): 3 Searcher Case Studies

My Guests If one were to attend a randomly selected group of Search Fund conferences, they’d be forgiven for thinking that every search fund is a smashing success. When I was both a searcher and a CEO, I often left these types of events with a certain sense of insecurity and self-doubt, as everybody seemed…

Kent Weaver: Building, Working With, and Learning from your Board of Directors

My Guest Today, I was thrilled to be joined by Kent Weaver. Early in his career, Kent was an acquisition entrepreneur, having acquired Sacramento-based Progressive Home Care. Subsequent to the acquisition, Kent ran the company for approximately 9 years before a successful exit. He has been investing in small and medium-sized businesses ever since. Kent…

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 Health…

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 realities…


MANAGING YOUR BUSINESS

Dr. Victoria Medvec on the Art and Science of High Stakes Negotiations

My Guest Dr. Victoria Medvec is the Adeline Barry Davee Professor of Management and Organizations at the Kellogg School of Management at Northwestern University. In addition to her professorship, Dr. Medvec is a co-founder and the Executive Director of the Center for Executive Women at the Kellogg School and the CEO of Medvec and Associates,…

A Deep Dive on Compensation

Listen in Your Browser Questions Asked Verne Harnish: Crafting Company-Wide Compensation Plans (3:06) Verne Harnish is the founder of the Entrepreneurs’ Organization (“EO” for short), a global network of entrepreneurs and CEOs that boasts over 16,000 members worldwide. He is the author of multiple global bestselling books including Mastering the Rockefeller Habits, and Scaling Up,…

A Deep Dive on Hiring

Listen in Your Browser Questions Asked Randy Street (3:30) Many of you will know Randy Street as co-author of the book Who: The A Method for Hiring, which introduced the now widely used Topgrading hiring method to the world. The book went on to become a New York Times, Wall Street Journal, BusinessWeek, USA Today,…

The Smallest Changes That Had the Largest Impacts: 4 CEO Case Studies

My Guests This is a very special episode of In The Trenches: In today’s episode, I will be interviewing 4 different CEOs of 4 different SMBs, and asking them just a single question: “What are some of the seemingly small changes you’ve made that have had the largest impacts?” When taking over a new business,…

Mike Zani, CEO of The Predictive Index: Hiring, Personality Profiling Tools, Working with a Partner, and Other Lessons from 20 Years as a CEO

My Guests My guest today is Mike Zani, CEO of The Predictive Index. The Predictive Index serves more than 9,000 clients across 142 countries, helping businesses optimize their hiring and team composition decisions through a combination of behavioral science, software, and professional consulting from the world’s top workplace behavior specialists. Mike has been CEO of…

Brent Beshore: The “Forrest Gump of Private Equity”

My Guest My guest today is Brent Beshore, Founder and CEO of Permanent Equity, a private investment firm that invests in Founder-owned private companies. Permanent Equity is a long-term investor that typically intends to hold portfolio companies indefinitely, often without the use of any leverage. In addition to his role as an investor, Brent is…

A.J. Wasserstein: Reflections of a Founder, CEO, Investor and Educator

My Guest My guest today is A.J. Wasserstein, the Eugene F. Williams, Jr. Lecturer in the Practice of Management at the Yale School of Management. His research, writing, and teaching concentrates on search funds, entrepreneurship, programmatic acquisitions, and small businesses. In addition to his role as an educator, A.J. is also a private investor in…

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 was…

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 a…

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 that…

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 to…

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 collaboration…

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 at…

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 less…

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, grew…

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 grew…


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 Electrical…

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 of…

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 at…


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 of…

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 experience…

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