In The Trenches
By Steve Divitkos
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Category: Entrepreneurship
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Subscribers: 3
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Episodes: 138
Description
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 single goal: To improve the personal and professional lives of Entrepreneurs and CEOs running SMBs.
| Episode | Date |
|---|---|
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Hiring Your Second in Command: With Cameron Herold, Founder of the COO Alliance and Former COO of 1-800-GOT-JUNK
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Apr 16, 2026 |
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Identifying the Irrational Beliefs Hindering Your Decision Making
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Apr 02, 2026 |
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"Great CEOs Are Lazy": Why the Best SMB Leaders Do Less—But Achieve More
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Mar 19, 2026 |
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Are Search Funds Moving Up Market?
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Mar 05, 2026 |
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The Four Stages of Leadership Maturity: Why the CEO Must Change Before the Company Can
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Feb 19, 2026 |
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“Don’t F*ck It Up": Les Trachtman on Avoiding Post-Close Founder Succession Mistakes
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Feb 05, 2026 |
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Why Most Incentive Plans Fail—and How Thoughtful CEOs Get Them Right
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Jan 20, 2026 |
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Installing an Operating System in Your Business: Lessons from Real EOS Implementations
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Jan 08, 2026 |
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The Working Capital Adjustment
|
Dec 23, 2025 |
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Hard to Kill: A Four-Part Framework for Evaluating Small Business Acquisitions
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Dec 11, 2025 |
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Facing the Worst-Case Scenario: How Jed Morris Lost His Business and Rebuilt His Life
|
Nov 27, 2025 |
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How AI is Transforming the Acquisition and Operations of Small Businesses
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Nov 13, 2025 |
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Technical Debt: What it is, How Much of it You Can Live With, and How to Incorporate it into an Investment Thesis
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Oct 30, 2025 |
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Announcing the Launch of Mineola Fund II
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Oct 22, 2025 |
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Stress, Panic Attacks, Debilitating Anxiety, and a $170M Exit: iContact Founder Aaron Houghton
|
Oct 16, 2025 |
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Rob Markey: Creator of the Net Promoter Score and Founder of Bain's Global Customer Strategy Practice
|
Oct 02, 2025 |
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Building Better CEOs: Lessons From a Veteran Executive Coach
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Sep 18, 2025 |
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The Acquisition Entrepreneur and Mental Health
|
Aug 28, 2025 |
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Evaluating Customer Retention in Recurring Revenue Businesses: With Craig Zingerline
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Aug 14, 2025 |
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Rethinking Asset Intensity in Search Fund Acquisitions
|
Jul 31, 2025 |
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Should Search Funds Buy Healthcare Practices? A Deep Dive with Scott Becker
|
Jul 17, 2025 |
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A Finance Survival Guide for SMB CEOs: Liquidity, Hiring, Budgeting, Capital Allocation & More
|
Jul 03, 2025 |
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Is Home Services Still a Good Bet? A Veteran Operator’s Take on a Saturated Market
|
Jun 19, 2025 |
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How to Price, Structure, and Diligence Around Customer Concentration
|
Jun 05, 2025 |
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A Playbook for Growing People-Intensive Service Companies
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May 22, 2025 |
|
How to Raise Prices Without Losing Customers—with Casey Brown
|
May 08, 2025 |
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The Entrepreneur’s Guide to Keeping Your Sh*t Together: With Dr. Sherry Walling
|
Apr 24, 2025 |
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The Art (and Science) of Building a High-Performance Sales Organization
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Apr 10, 2025 |
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A Super Primer on Evaluating and Acquiring a Software Company
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Mar 28, 2025 |
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Randy Street: Pioneer of the Topgrading Hiring Method & Co-Author of “Who: The A-Method for Hiring”
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Mar 13, 2025 |
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Is the Search Fund Acquisition Rate Falling? With Jim Edmunds, Badge Stone & Kent Weaver
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Feb 27, 2025 |
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How to Avoid Common Stumbling Blocks in an M&A Process: With Raam Jani
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Feb 12, 2025 |
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How to Get Your Exit Proceeds (Mostly) Tax Free
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Jan 30, 2025 |
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Dr. Daniel Crosby: How our Psychology Impacts our Spending, Investing and Risk Taking Decisions
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Jan 16, 2025 |
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Long Term Holds: With Zac Carman, CEO of ConsumerAffairs for 14+ Years
|
Jan 02, 2025 |
|
Leverage: Doing More With Less
|
Dec 19, 2024 |
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"Like Changing Tires on a Moving Car": The Unseen Realities of Managing Rapid Growth
|
Dec 05, 2024 |
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Achieving the Entrepreneurial Dream Through Franchise Ownership
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Nov 21, 2024 |
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An Investing Masterclass with Brent Beshore
|
Nov 07, 2024 |
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Five Ideas That Every CEO Should Know
|
Oct 24, 2024 |
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In Conversation with 3 Founders Who Sold Their Companies to Search Funds
|
Oct 10, 2024 |
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How to Build a Business that will Attract a Private Equity Buyer
|
Sep 26, 2024 |
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The Link Between Money, Meaning, and Happiness
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Sep 12, 2024 |
|
The Entrepreneur and the Spousal Relationship: Part 2
|
Aug 29, 2024 |
|
Dr. Bill Hudenko: Professor of Psychology at the Dartmouth School of Medicine and a 4x Founder & CEO
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Aug 15, 2024 |
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From Combat to Classrooms: How Jim Vesterman Went from Special Forces to a 13.5x Return in 8 Years
|
Aug 01, 2024 |
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17 Lessons on the Psychology of Being a Searcher and CEO
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Jul 18, 2024 |
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You Don't Have an Engineering Problem, You Have a Product Management Problem
|
Jul 04, 2024 |
|
Evaluating The Most Common Forms of Debt Used to Finance Small Business Acquisitions
|
Jun 20, 2024 |
|
From $7M to $50M via 14 Acquisitions: A Consolidation Success Story With Jay Davis & Jason Pananos
|
Jun 06, 2024 |
|
Why You May Be Ignoring Brokered Deals at Your Peril
|
May 23, 2024 |
|
Why You May Want to Reconsider Your Industry Roll-up Strategy
|
May 09, 2024 |
|
45 (More) Things That I Think Are True
|
Apr 25, 2024 |
|
The Constellation Software Playbook for Acquiring and Growing Software Companies
|
Apr 11, 2024 |
|
Evaluating Stock Options as Attraction, Retention, and Incentive Alignment Tools
|
Mar 28, 2024 |
|
Can Ambition and Inner Peace Coexist? With Rob Dube
|
Mar 14, 2024 |
|
Answers to Recurring FAQs from Current and Prospective Searchers
|
Feb 29, 2024 |
|
Profit Before Anything Else: With Mike Michalowicz, Author of "Profit First"
|
Feb 14, 2024 |
|
Royce Yudkoff & Rick Ruback: Educators, Mentors, and Leaders Within the SMB Community
|
Feb 01, 2024 |
|
Jeff Stevens & A.J. Wasserstein on The Future of Entrepreneurship Through Acquisition
|
Jan 18, 2024 |
|
Michael Girdley on The Rise of Holding Companies
|
Jan 04, 2024 |
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Questions You Should Be Prepared to Answer Before Buying (or Selling) a Small Business
|
Dec 21, 2023 |
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What I'd Change if I Could Re-Do the First 90 Days of my Search: 3 Searcher Case Studies
|
Dec 07, 2023 |
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Dr. Victoria Medvec on the Art and Science of High Stakes Negotiations
|
Nov 23, 2023 |
|
Peter Lehrman, Founder & CEO of Axial, The Largest Online Marketplace to Buy & Sell SMBs
|
Nov 09, 2023 |
|
Conscious Leadership with Executive Coach and Best-Selling Author Kaley Klemp
|
Oct 26, 2023 |
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Building a $5.5B Mid-Market Private Equity Firm: Brent Belzberg, Founder of Torquest Partners
|
Oct 12, 2023 |
|
My Experience With Anxiety
|
Sep 28, 2023 |
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A Deep Dive on Compensation
|
Sep 14, 2023 |
|
A Deep Dive on Hiring
|
Aug 31, 2023 |
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"A Guide to the Good Life": What Entrepreneurs Can Learn From Stoic Philosophy
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Aug 17, 2023 |
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Venture Capital “Orphans”: Exploring an Emerging Search Fund Investment Thesis
|
Aug 03, 2023 |
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When Search Funds Don’t Go As Planned (Part 2): With Jim Sharpe
|
Jul 22, 2023 |
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Lessons Learned From 400+ Post-Exit Entrepreneurs: John Warrillow, Host of Built to Sell Radio
|
Jul 22, 2023 |
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When Search Funds Don't Go As Planned (Part 1): 3 Searcher Case Studies
|
Jun 22, 2023 |
|
75 Things That I Think Are True
|
Jun 08, 2023 |
|
The SMB Credit Markets: Bank Failures, Rising Interest Rates, and a Looming Recession
|
May 25, 2023 |
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The Merits, Risks, and Possible Unintended Consequences of Earn-Outs
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May 11, 2023 |
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Mental Health for High Achievers: Ambition, Anxiety, Perfectionism, and Balancing Striving vs. Self-Acceptance
|
Apr 27, 2023 |
|
The 2023 SaaS CEO Survey
|
Apr 13, 2023 |
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Kent Weaver: Building, Working With, and Learning from your Board of Directors
|
Mar 29, 2023 |
|
How to Know When it's Time to Stop
|
Mar 22, 2023 |
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Are You Selling to the Wrong Customers?
|
Mar 16, 2023 |
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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
|
Mar 02, 2023 |
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Evaluating the Correlation Between Hours Worked and Success Achieved
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Feb 16, 2023 |
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The Smallest Changes That Had The Largest Impacts: 4 CEO Case Studies
|
Feb 02, 2023 |
|
Constructing, Managing, and Working with a Board of Directors
|
Jan 19, 2023 |
|
Mike Zani, CEO of The Predictive Index: Hiring, Personality Profiling Tools, Working with a Partner, and Other Lessons from 20 Years as a CEO
|
Jan 05, 2023 |
|
The Current State of the Debt Capital Markets
|
Dec 22, 2022 |
|
Evaluating 5 Very Different Approaches to Acquiring a Software Company
|
Dec 08, 2022 |
|
Brent Beshore: The "Forrest Gump of Private Equity"
|
Nov 24, 2022 |
|
Tools in Managing my own Psychology
|
Nov 10, 2022 |
|
A.J. Wasserstein: Reflections of a Founder, CEO, Investor and Educator
|
Oct 27, 2022 |
|
The CEO as Chief Capital Allocator
|
Oct 13, 2022 |
|
Buy at 5X EBITDA, Sell at 8X Revenue: The On-Premise to SaaS Transition of FieldEdge
|
Sep 29, 2022 |
|
Knowing Who, When, and How to Fire
|
Sep 15, 2022 |
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Sell-Side M&A Advisors: How to Choose One, How Much They Cost, and The Importance of the "Fine Print"
|
Sep 01, 2022 |
|
Strategic Considerations When Evaluating a Letter of Intent to Sell Your Business
|
Aug 04, 2022 |
|
All Things Finance & Accounting: Managing Cash & Liquidity, Employee Financial Literacy, Capital Allocation, Preparing for Macroeconomic Turbulence, and Hiring Your First CFO
|
Jul 21, 2022 |
|
Busting the Biggest Myth About Purchasing and Operating Small Companies
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Jul 07, 2022 |
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Running a Business During Inflationary Periods and Understanding Pricing Power (with Jim Sharpe)
|
Jun 23, 2022 |
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The Biggest Temptation of a Software CEO
|
Jun 09, 2022 |
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Employee Burnout and The Great Resignation
|
May 26, 2022 |
|
Should You Become an Entrepreneur?
|
May 12, 2022 |
|
Having Hard Conversations (Live Panel Discussion from 2022 MIT Sloan Search Fund Summit)
|
Apr 28, 2022 |
|
A Leader’s Most Important Skill
|
Apr 14, 2022 |
|
Quality of Earnings Analysis: What You Need to Know Before Buying a Business
|
Mar 31, 2022 |
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Lessons Learned in Capitalizing an Acquisition
|
Mar 17, 2022 |
|
Aaron Ross: Author of "Predictable Revenue" and "From Impossible to Inevitable"
|
Mar 03, 2022 |
|
The Entrepreneur and the Spousal Relationship
|
Feb 17, 2022 |
|
Bob Pritchett: Author of "Fire Someone Today" and Founder & Executive Chairman of Faithlife Software
|
Feb 03, 2022 |
|
The Working Capital Adjustment
|
Jan 20, 2022 |
|
All Things Hiring with Randy Street: Co-Author of " Who: The A-Method for Hiring" and Vice Chairman of ghSMART
|
Jan 06, 2022 |
|
Considerations Unique to Acquiring a Software Company (Product)
|
Dec 23, 2021 |
|
Verne Harnish: Founder of The Entrepreneurs' Organization (EO), Author of "Scaling Up" and "Mastering the Rockefeller Habits"
|
Dec 09, 2021 |
|
Implementing a Formal Operating System Like EOS or the Rockefeller Habits
|
Nov 25, 2021 |
|
The Realities of Managing Extremely Rapid Growth
|
Nov 11, 2021 |
|
Considerations Unique to Acquiring a Software Company (Financial)
|
Oct 28, 2021 |
|
What M&A Lawyers Want CEOs to Know About Selling Their Companies
|
Oct 14, 2021 |
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Lessons From my First Month as the CEO of a Newly Acquired Company
|
Sep 30, 2021 |
|
Rich Manders: Lessons from Founding, Growing, Buying, Selling, Coaching, and Investing in SMBs
|
Sep 16, 2021 |
|
Why Your Business Needs a Set of Core Values (or Why Yours May Not be Having an Impact)
|
Sep 02, 2021 |
|
Building and Managing a World Class Product Management Discipline
|
Aug 19, 2021 |
|
Busting the Biggest Myth About Selling Your Business
|
Aug 05, 2021 |
|
Understanding and Managing The Psychological Toll of Being an Entrepreneur or CEO
|
Jul 22, 2021 |
|
Lessons in Managing my own Psychology
|
Jul 08, 2021 |
|
CEO Coaches: What do they do, how do they work with CEOs, and why might you consider hiring one?
|
Jun 24, 2021 |
|
Migrating Your Software Company from On-Premise to SaaS (Part 2)
|
Jun 10, 2021 |
|
What I Learned During my First (Failed) Attempt to Sell my Business
|
Jun 04, 2021 |
|
Considerations in Selecting Your M&A Advisor
|
Jun 02, 2021 |
|
Pricing Power: How Small Changes Can Have Big Impacts
|
May 30, 2021 |
|
The Private Equity Perspective on Acquiring, Operating, and Selling Software Companies
|
May 27, 2021 |
|
Migrating Your Software Company from On-Premise to SaaS (Part 1)
|
May 26, 2021 |
|
Hiring Your Senior Leadership Team
|
May 17, 2021 |
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Why So Many Companies Rarely Achieve Their Annual Goals
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May 17, 2021 |
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The Entrepreneur and Mental Health (Part 2): My Advice to You
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May 13, 2021 |
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Sales: Hiring, Onboarding, Compensating, Scaling & Supporting a World Class Sales Team
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Apr 29, 2021 |
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In The Trenches (Trailer)
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Apr 19, 2021 |