The Deep Wealth Podcast - Unlock Your Deep Wealth In Business and Life

Deep Wealth by Jeffrey Feldberg
  • 5.0 (52)
  • Entrepreneurship
  • Updated Weekly

Your business is your legacy, but does it own you? Most entrepreneurs aren’t ready:  90% of exits fail, and founders leave 50-100%+ of the deal value behind. Not from a bad business, but poor preparation. The Deep Wealth Podcast, hosted by Jeffrey Feldberg, who built a startup from his parents’ attic, rejected a 7-figure offer, and secured a 9-figure exit in 24 months, shares his 90-day Deep Wealth Mastery system. Join top founders and dealmakers for proven exit strategies and profit-boosting tips to build a self-managing business and land a legacy-defining deal. Don’t let regret steal your millions.  Subscribe at https://iapdw.com/podcast to unlock your freedom and build your golden legacy.

  1. 1d ago

    Founder Casey Woo: Are You Hiring Specialists When You Need Scalers? (#589)

    Send us Fan Mail “Make space and pause to improve life significantly.” -Casey Woo Exclusive Insights from This Week's Episodes Your hiring process may reward specialists while filtering out the operators your next stage of growth requires. Founder Casey Woo reveals why scalers thrive across functions when the playbook breaks. Episode Highlights [00:13:02] Why Casey says leaving Wall Street was not courage but an "allergic reaction" to the wrong work [00:15:54] The traits that reveal whether someone is a scaler hiding inside a conventional job title [00:17:25] Why scalers resist specialization and become "specialists at being generalists" [00:20:28] How Operators Guild scaled from nine people to 1,200 without sacrificing intimacy [00:24:05] Why cross-functional operators may learn more from each other than from function-specific groups [00:28:30] The leadership value of finding people who understand your problems without explanation or judgment [00:36:46] The familiar "jack of all trades" belief that may be causing founders to undervalue generalists Full show notes, transcript, and resources for this episode: https://podcast.deepwealth.com/589 The Deep Wealth Podcast Most entrepreneurs do not fail. They just carry too much for too long. The business grows. Pressure grows faster. Profits get harder to predict. Decisions cost more energy. Over time, focus slips and health takes the hit. The Deep Wealth Podcast and Deep Wealth Mastery are built from real experience. We're the only system based on a 9-figure exit. This system exists because guessing gets expensive. 🧠 Deep Wealth Mastery This is for you if you want to:  • Grow a profitable business without becoming the bottleneck  • Build real value so selling is optional, not forced  • Optimize your health before it limits your business and life One proven roadmap for real decisions. ⭐ Explore Deep Wealth Mastery https://iapdw.com/idm 🎧 Subscribe https://iapdw.com/podcast 📘 Free eBook https://iapdw.com/ebook 💬 Have a question you keep circling back to? Leave a short voicemail https://podcast.deepwealth.com/voicemail/ Built by entrepreneurs. For entrepreneurs.

    Founder Casey Woo: Are You Hiring Specialists When You Need Scalers? (#589)

  2. 6d ago

    Founder Craig Ceccanti: Your Business Is Growing. Why Does Your Life Keep Shrinking? (#588)

    Send us Fan Mail “Believe in yourself and enjoy the journey.” -Craig Ceccanti Exclusive Insights from This Week's Episodes Your company can grow while your freedom disappears. Founder Craig Ceccanti reveals how founder dependency creates team frustration, growth ceilings, and buyer risk, and why building a business that runs without you changes everything. Episode Highlights [00:08:00] The birthday party interruption that exposed Craig as the bottleneck in his own company [00:11:13] Why capable leadership teams fail when trust keeps the real problems off the table [00:16:32] The founder ego trap that makes outside systems and experienced help feel unnecessary [00:19:24] Why the skills that get you to $1 million can fail you on the road to $10 million [00:22:11] The missing number two that leaves visionary founders trapped in day-to-day execution [00:24:57] Why owner reliance creates a growth ceiling and becomes a serious future buyer concern [00:36:36] The success regret founders discover when the business wins but the family quietly loses Full show notes, transcript, and resources for this episode: https://podcast.deepwealth.com/588 The Deep Wealth Podcast Most entrepreneurs do not fail. They just carry too much for too long. The business grows. Pressure grows faster. Profits get harder to predict. Decisions cost more energy. Over time, focus slips and health takes the hit. The Deep Wealth Podcast and Deep Wealth Mastery are built from real experience. We're the only system based on a 9-figure exit. This system exists because guessing gets expensive. 🧠 Deep Wealth Mastery This is for you if you want to:  • Grow a profitable business without becoming the bottleneck  • Build real value so selling is optional, not forced  • Optimize your health before it limits your business and life One proven roadmap for real decisions. ⭐ Explore Deep Wealth Mastery https://iapdw.com/idm 🎧 Subscribe https://iapdw.com/podcast 📘 Free eBook https://iapdw.com/ebook 💬 Have a question you keep circling back to? Leave a short voicemail https://podcast.deepwealth.com/voicemail/ Built by entrepreneurs. For entrepreneurs.

    Founder Craig Ceccanti: Your Business Is Growing. Why Does Your Life Keep Shrinking? (#588)

  3. Oct 20

    UFC Hall of Famer Pat Miletich: Living Healthy but Feeling Drained? Ask This One Question. (#587)

    Send us Fan Mail “The only time you have trouble in your life is when you don’t listen to your intuition.” -Pat Miletich Exclusive Insights from This Week's Episodes Living healthy but still feeling drained? UFC Hall of Famer Pat Miletich challenges founders to stop treating symptoms and ask what is causing them. Discover the root-cause mindset that can protect health, leadership capacity, and business performance. Episode Highlights [00:04:28] Pat reveals how struggling to breathe taught him that harder work cannot always overcome a hidden constraint [00:11:51] The competitor question that forces founders to confront weaknesses before the market exposes them [00:22:59] Why Pat ignores the visible symptom and asks what underlying problem made it possible [00:26:09] The hidden price of shortcuts and why convenience can quietly create bigger problems [00:28:56] Why accepting low energy as “just getting older” may stop you from asking better questions [00:39:13] Pat shares one simple food-shopping habit for people who want to start questioning their inputs Full show notes, transcript, and resources for this episode: https://podcast.deepwealth.com/587 The Deep Wealth Podcast Most entrepreneurs do not fail. They just carry too much for too long. The business grows. Pressure grows faster. Profits get harder to predict. Decisions cost more energy. Over time, focus slips and health takes the hit. The Deep Wealth Podcast and Deep Wealth Mastery are built from real experience. We're the only system based on a 9-figure exit. This system exists because guessing gets expensive. 🧠 Deep Wealth Mastery This is for you if you want to:  • Grow a profitable business without becoming the bottleneck  • Build real value so selling is optional, not forced  • Optimize your health before it limits your business and life One proven roadmap for real decisions. ⭐ Explore Deep Wealth Mastery https://iapdw.com/idm 🎧 Subscribe https://iapdw.com/podcast 📘 Free eBook https://iapdw.com/ebook 💬 Have a question you keep circling back to? Leave a short voicemail https://podcast.deepwealth.com/voicemail/ Built by entrepreneurs. For entrepreneurs.

    UFC Hall of Famer Pat Miletich: Living Healthy but Feeling Drained? Ask This One Question. (#587)

  4. Oct 15

    Behavioral Economist Etinosa Agbonlahor: Your Customers Would Pay More. Why Are You Charging Less? (#586)

    Send us Fan Mail “Keep going.” -Etinosa Agbonlahor Exclusive Insights from This Week's Episodes Your customers may value your offer more than your price suggests. Behavioral Economist Etinosa Agbonlahor exposes how founders guess, discount too quickly, and confuse activity with profit. Discover what your pricing may be costing you. Episode Highlights [00:09:12] Why the same product can become worth three times more when context changes [00:12:03] The tyranny of low prices and why cheap can quietly damage perceived value [00:16:10] Three pricing mistakes quietly costing growing companies sales and profit [00:20:44] Why discounting can turn a winning sale into a money losing customer [00:28:46] How customer research replaces pricing anxiety with evidence and confidence [00:36:34] Why successful companies still guess at pricing and leave money on the table [00:42:18] The dangerous founder mistake of confusing activity with profitability Full show notes, transcript, and resources for this episode: https://podcast.deepwealth.com/586  Behavioral Pricing Playbook (Practical strategies for understanding how customers value what you offer.) https://playbook.decisionalpha.co Stress-Test Your Pricing Strategy with Fred (Receive tailored pricing recommendations in minutes.) https://fred.decisionalpha.co How to Talk to Your Parents About Money (A Short Practical Guide: Conversations That Build Peace, Confidence, and Financial Security) https://www.amazon.com/Talk-Your-Parents-About-Money-ebook/dp/B0DNRTKSLH The Deep Wealth Podcast Most entrepreneurs do not fail. They just carry too much for too long. The business grows. Pressure grows faster. Profits get harder to predict. Decisions cost more energy. Over time, focus slips and health takes the hit. The Deep Wealth Podcast and Deep Wealth Mastery are built from real experience. We're the only system based on a 9-figure exit. This system exists because guessing gets expensive. 🧠 Deep Wealth Mastery This is for you if you want to:  • Grow a profitable business without becoming the bottleneck  • Build real value so selling is optional, not forced  • Optimize your health before it limits your business and life One proven roadmap for real decisions. ⭐ Explore Deep Wealth Mastery https://iapdw.com/idm 🎧 Subscribe https://iapdw.com/podcast 📘 Free eBook https://iapdw.com/ebook 💬 Have a question you keep circling back to? Leave a short voicemail https://podcast.deepwealth.com/voicemail/ Built by entrepreneurs. For entrepreneurs.

    Behavioral Economist Etinosa Agbonlahor: Your Customers Would Pay More. Why Are You Charging Less? (#586)

  5. Oct 13

    Dr. Kyle Hulsebus: What If Your Best Years Begin After 40? (#585)

    Send us Fan Mail “There are no mistakes, keep doing it.” -Kyle Hulsebus Exclusive Insights from This Week's Episodes Your 40s can expose years of ignored health patterns or become the start of your strongest chapter. Dr. Kyle Hulsebus reveals why founders must track the health behind their performance. Episode Highlights [00:17:28] The founder health patterns that appear when business pressure becomes physical [00:21:20] Why recurring symptoms become dangerous when founders accept them as normal [00:24:01] The health KPIs that go far beyond sleep, exercise, and physical fitness [00:29:30] Why your 40s may be the beginning of your strongest and most productive years [00:35:41] How small daily choices can quietly compound into larger health consequences [00:38:39] Two simple practices to reset before high-pressure decisions and improve recovery [00:45:15] Why health means wholeness across your body, business, finances, and relationships Full show notes, transcript, and resources for this episode: https://podcast.deepwealth.com/585 The Deep Wealth Podcast Most entrepreneurs do not fail. They just carry too much for too long. The business grows. Pressure grows faster. Profits get harder to predict. Decisions cost more energy. Over time, focus slips and health takes the hit. The Deep Wealth Podcast and Deep Wealth Mastery are built from real experience. We're the only system based on a 9-figure exit. This system exists because guessing gets expensive. 🧠 Deep Wealth Mastery This is for you if you want to:  • Grow a profitable business without becoming the bottleneck  • Build real value so selling is optional, not forced  • Optimize your health before it limits your business and life One proven roadmap for real decisions. ⭐ Explore Deep Wealth Mastery https://iapdw.com/idm 🎧 Subscribe https://iapdw.com/podcast 📘 Free eBook https://iapdw.com/ebook 💬 Have a question you keep circling back to? Leave a short voicemail https://podcast.deepwealth.com/voicemail/ Built by entrepreneurs. For entrepreneurs.

    Dr. Kyle Hulsebus: What If Your Best Years Begin After 40? (#585)

  6. Oct 8

    Leadership Expert Michael Fineman: Everyone Says You’re Winning. Why Doesn’t It Feel Like It? (#584)

    Send us Fan Mail “You are not alone. You are loved as a child of the most high God.” -Michael Fineman Exclusive Insights from This Week's Episodes Everyone says you’re winning, yet something feels off. Leadership Expert Michael N. Fineman reveals how small compromises create Authority Drift, turning founders reactive and pulling success away from what they actually want. Episode Highlights [00:22:33] The post-exit lesson Michael learned after compromises left him unsure who he was [00:28:31] Why founders can drift furthest from themselves while the business appears successful [00:31:33] How to identify the first compromise that quietly moved you away from your original vision [00:35:21] The question Michael was afraid to ask himself: “What do I want?” [00:39:30] Why external pressure turns founders reactive and pushes strategy out of the room [00:44:18] Founder’s disorder: when refusing to delegate makes growth increasingly unsustainable [00:52:05] Why noticing the drift without condemning yourself may be the most important first move Full show notes, transcript, and resources for this episode: https://podcast.deepwealth.com/584 The Deep Wealth Podcast Most entrepreneurs do not fail. They just carry too much for too long. The business grows. Pressure grows faster. Profits get harder to predict. Decisions cost more energy. Over time, focus slips and health takes the hit. The Deep Wealth Podcast and Deep Wealth Mastery are built from real experience. We're the only system based on a 9-figure exit. This system exists because guessing gets expensive. 🧠 Deep Wealth Mastery This is for you if you want to:  • Grow a profitable business without becoming the bottleneck  • Build real value so selling is optional, not forced  • Optimize your health before it limits your business and life One proven roadmap for real decisions. ⭐ Explore Deep Wealth Mastery https://iapdw.com/idm 🎧 Subscribe https://iapdw.com/podcast 📘 Free eBook https://iapdw.com/ebook 💬 Have a question you keep circling back to? Leave a short voicemail https://podcast.deepwealth.com/voicemail/ Built by entrepreneurs. For entrepreneurs.

    Leadership Expert Michael Fineman: Everyone Says You’re Winning. Why Doesn’t It Feel Like It? (#584)

  7. Oct 6

    Founder & CFO Matt Putra: The Numbers Are Lying. Here's What To Do Before Cash Breaks (#583)

    Send us Fan Mail “Believe in yourself and take more risks.” -Matt Putra Exclusive Insights from This Week's Episodes Your numbers can look healthy while cash quietly moves toward trouble. Founder & CFO Matt Putra reveals how one source of truth, better decisions, and team alignment protect cash and enterprise value. Episode Highlights [00:09:37] The value compounding engine: see the truth, decide, then align [00:13:33] How a $700,000 forecast miss turned into a dangerous cash deficit [00:17:14] Why competing spreadsheets quietly destroy decision quality and trust [00:20:45] The first 10 days Matt uses to expose a company's biggest risks and opportunities [00:31:29] The one constraint that can produce the highest return with the lowest risk [00:41:06] The one financial discipline Matt would install in almost every company [00:44:58] How growth, quality, and risk influence what a future buyer may pay Full show notes, transcript, and resources for this episode: https://podcast.deepwealth.com/583 https://podcast.deepwealth.com/252 The Deep Wealth Podcast Most entrepreneurs do not fail. They just carry too much for too long. The business grows. Pressure grows faster. Profits get harder to predict. Decisions cost more energy. Over time, focus slips and health takes the hit. The Deep Wealth Podcast and Deep Wealth Mastery are built from real experience. We're the only system based on a 9-figure exit. This system exists because guessing gets expensive. 🧠 Deep Wealth Mastery This is for you if you want to:  • Grow a profitable business without becoming the bottleneck  • Build real value so selling is optional, not forced  • Optimize your health before it limits your business and life One proven roadmap for real decisions. ⭐ Explore Deep Wealth Mastery https://iapdw.com/idm 🎧 Subscribe https://iapdw.com/podcast 📘 Free eBook https://iapdw.com/ebook 💬 Have a question you keep circling back to? Leave a short voicemail https://podcast.deepwealth.com/voicemail/ Built by entrepreneurs. For entrepreneurs.

    Founder & CFO Matt Putra: The Numbers Are Lying. Here's What To Do Before Cash Breaks (#583)

  8. Oct 1

    Founder Teresa Reile: They Said She’d Fail. Six Months Later, She Had 60% of the Market (#582)

    Send us Fan Mail “It’s not about chasing the dollar, it’s about the dream. Go with purpose.” -Teresa Reile Exclusive Insights from This Week's Episodes They said Founder Teresa Reile would fail. Six months later, she had 60% of the market. Discover how solving an ignored customer problem can turn skepticism into market disruption. Episode Highlights [00:04:06] Teresa reveals why stepping into businesses she did not fully understand became part of her founder advantage. [00:07:58] From a few trucks to 60% market share, then an eight figure sale. [00:07:58] Teresa explains why she would rather create a market than compete inside an existing one. [00:21:12] Why founder energy and health can quietly influence culture across the entire organization. [00:26:10] Teresa shares why lighter effort, experimentation, and keeping business fun can unlock action. [00:44:39] The health topic Teresa believes founders should become curious about before symptoms force the issue. [00:46:15] Her post-success lesson: stop chasing only the dollar and protect time with the people who matter. Full show notes, transcript, and resources for this episode: https://podcast.deepwealth.com/582 The Deep Wealth Podcast Most entrepreneurs do not fail. They just carry too much for too long. The business grows. Pressure grows faster. Profits get harder to predict. Decisions cost more energy. Over time, focus slips and health takes the hit. The Deep Wealth Podcast and Deep Wealth Mastery are built from real experience. We're the only system based on a 9-figure exit. This system exists because guessing gets expensive. 🧠 Deep Wealth Mastery This is for you if you want to:  • Grow a profitable business without becoming the bottleneck  • Build real value so selling is optional, not forced  • Optimize your health before it limits your business and life One proven roadmap for real decisions. ⭐ Explore Deep Wealth Mastery https://iapdw.com/idm 🎧 Subscribe https://iapdw.com/podcast 📘 Free eBook https://iapdw.com/ebook 💬 Have a question you keep circling back to? Leave a short voicemail https://podcast.deepwealth.com/voicemail/ Built by entrepreneurs. For entrepreneurs.

    Founder Teresa Reile: They Said She’d Fail. Six Months Later, She Had 60% of the Market (#582)
See All (589)

5
out of 5
52 Ratings

About

Your business is your legacy, but does it own you? Most entrepreneurs aren’t ready:  90% of exits fail, and founders leave 50-100%+ of the deal value behind. Not from a bad business, but poor preparation. The Deep Wealth Podcast, hosted by Jeffrey Feldberg, who built a startup from his parents’ attic, rejected a 7-figure offer, and secured a 9-figure exit in 24 months, shares his 90-day Deep Wealth Mastery system. Join top founders and dealmakers for proven exit strategies and profit-boosting tips to build a self-managing business and land a legacy-defining deal. Don’t let regret steal your millions.  Subscribe at https://iapdw.com/podcast to unlock your freedom and build your golden legacy.

Information