CEO Mistakes

Jeffrey Pomeranz
  • 5.0 (3)
  • Entrepreneurship
  • Weekly

CEO Mistakes features honest, unfiltered conversations with successful founders, operators, and business leaders. We dive into the critical missteps and hard-won lessons that shaped their careers, to help YOU avoid the same pitfalls and build a more resilient business.

Episodes

  1. 2d ago

    Real Estate Investor: "The Market Tried To Destroy Me -So I Had To Change Everything"

    What would you do if growing your business meant doing more work for less money? In this episode of CEO Mistakes, Eric Martel, real estate investor and CEO of Martel Turnkey, shares how scaling to 50+ properties a month ate into his margins, why he shut down a trucking company and a title company that looked like sure things, and how his Flip System coaching program evolved to get clients to actually take action instead of just consuming content. In this episode, you’ll learn: Why scaling past your sweet spot can add headcount and complexity without adding profitHow cash flow forecasting, not your P&L, determines how fast you can safely growWhy strict controls on investor money protect you from accidental “rob Peter to pay Paul” situationsHow narrowing choices down to two options helps clients beat decision fatigue and take actionWhy you should never invest in a business that relies on an operator without deep industry knowledge and a proven track record Questions we cover: How did you buy an 8-unit apartment building at 18 with no money down?How far down the line were you before you realized more scale wasn’t the smart move?Where were you getting squeezed on margins?Of the 700 people in your program, what percentage actually did a deal?Have you started any businesses that you subsequently shut down?Timestamps: 00:00 Buying an 8-unit apartment building at 18 with no money down04:51 What Martel Turnkey does05:26 The scaling mistake: more deals, same profit11:01 Victims of their own success: raising neighborhood values15:09 Where the margins got squeezed19:20 Why cash flow determines how fast you can grow22:08 Tracking investor money and avoiding a Ponzi trap24:54 Launching the Flip System coaching program29:37 What to do when clients don’t take action32:43 Why customer success comes before revenue35:08 The copilot model: coaching clients through a real deal36:53 Beating decision fatigue with fewer options39:44 The trucking company that lost $50K a month43:33 The mistake: relying too heavily on one operator49:24 Why a “no-brainer” title company failed55:33 Final advice: be resilient and trust but verify58:05 How to connect with Eric Connect with Eric Martel: @ericmartelofficial Listen to CEO Mistakes:https://linktr.ee/CEOmistakes

  2. Oct 29

    The Social Media Expert: "If I Started Over, I'd Never Build The Same Business Again"

    Episode [03]: Jeff sits down with Adam Isaacs, CEO of Wildfire Video Group, to talk about waiting too long to niche down, paying for things clients didn’t actually value, and what he would do differently. In this episode: How niching down raised his cost per lead by 4-5x and still became the most profitable move he’s made, and how he learned clients valued the director more than the expensive shoots.What broke when one producer handled everything for each client, and the cost of keeping people on longer than he should have. Chapters:(00:00) What Wildfire Video Group does(01:06) His first client: his mom, a Boca Raton divorce lawyer(02:22) Five years of trying not to work with lawyers(05:05) The aha moment that made him niche down(06:46) Turning away business and paying 5x per lead(09:38) 30 to 90 videos a month per client(12:03) Paying for shoots clients didn’t value(14:06) The real activation point: the director, not the camera(16:05) Free market research from lost sales calls(20:43) Why lawyers struggle on social media(22:55) One producer per client, and why clients left with them(27:06) Scaling breakpoints and department heads(30:08) What he’d do differently: niche down even further(34:52) Managing expectations and online hate(38:45) Who actually wins on social(43:14) Keeping people on too long(45:26) Nick Saban, A-players, and rewarding effort(52:02) The one thing he’d tell his younger self(53:19) Reps: his cousin’s saxophone story(55:37) Where to find Adam Connect with Adam:Socials: @adamgrowfasterWebsite: wildfirevideo.com Watch the full episode on YouTube: https://www.youtube.com/channel/UCDgis0KouTxJgvJtALABFqQFollow CEO Mistakes: https://linktr.ee/CEOmistakes

  3. Oct 22

    Stop Negotiating Your Fees : Why Your Niche Is Your Leverage | Ron Krudo

    Ron spent two years and more research than he’d ever done for anyone chasing a client his young firm wasn’t built to win. The deal went to a bigger bank, and he learned what being a “yes man” really costs a CEO. Episode 02: Jeff sits down with Ron Krudo, CEO of Right Street Advisors , to talk about saying yes to every deal, client, and commitment, even the ones he wasn’t set up to win, and what he would do differently. In this episode: Why Ron lost a two-year pitch despite never being outbid on price or effortThe three changes he made after that loss, including bringing his team to the table, and how niching down to manufacturing improved his bottom line.The red flags he watches for, from clients who haggle fees to sellers who aren’t really ready to sell Chapters: (01:40) The two-year pitch for a client he couldn’t win (07:30) Three things he’d do differently (11:40) Niching down to manufacturing and industrials (13:45) Co-broke or go-broke: passing on off-fit deals (17:55) How handoffs cost him client relationships (20:00) Communication style as part of your brand (25:25) When to cut a difficult client (28:45) Red flags: fee negotiators and advice-ignorers (38:20) Taking on a deal with a valuation gap (41:15) “Do you want to sell?”: the question he asks every seller (46:40) Finding your why (56:15) Where to find Ron Connect with Ron: LinkedIn: https://www.linkedin.com/in/ron-krudo/Website: https://www.rightstreetadvisors.com/ Watch the full episode on YouTube: https://www.youtube.com/@ceomistakes Follow CEO Mistakes: https://linktr.ee/CEOmistakes

  4. Sep 11

    The Cost of Delaying a Pivot: Josh Blum on Adapting Before It's Too Late

    Josh Blum is an execution coach who works with business owners and leaders to turn long-term strategy into everyday decisions and results. With 20+ years in consultative sales and leadership, he brings a practical, human approach to clarity, momentum, and accountability. In this conversation, Josh and Jeff  discuss topics such as: - Why most strategic plans die between the boardroom and Monday morning - The hidden cost of owners who can’t step out of the day-to-day -How “positive accountability” differs from micromanaging, and why it actually works -What a real sounding board does for a leader that a team can’t - Lessons from 20 years of sales on getting people to commit to action 00:38 Tell me about the business you broke 00:56 Leaving a corporate career to launch in 2019 01:33 The business model: in-person corporate training 02:16 COVID hits and the business is “dead on arrival” 03:20 The pivot to online and B2C that failed 04:03 “Don’t quit” vs. knowing when to pivot 05:31 Why having cash reserves can slow you down 06:30 Hiring a consultant and the “perfect system” trap 08:10 Missing the leading indicators 09:15 Bringing business stress home to family 11:14 18 months without a paycheck 13:10 The lowest point: considering a return to corporate 14:28 Corporate risk vs. entrepreneurial risk 17:38 How a scarcity mindset compromises decisions 18:24 The turning point: finding clarity in late 2021 20:40 The big lesson: set a deadline and adapt fast 23:22 Spotting risk early in business today

    The Cost of Delaying a Pivot: Josh Blum on Adapting Before It's Too Late
  • 4 Episodes

Ratings & Reviews

5
out of 5
3 Ratings

About

CEO Mistakes features honest, unfiltered conversations with successful founders, operators, and business leaders. We dive into the critical missteps and hard-won lessons that shaped their careers, to help YOU avoid the same pitfalls and build a more resilient business.

Information

  • Creator
    Jeffrey Pomeranz
  • Years Active
    2026
  • Episodes
    4
  • Rating
    Explicit
  • Copyright
    © Jeffrey Pomeranz
  • Show Website
    CEO Mistakes

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