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

Deep Wealth by Jeffrey Feldberg
undefined
Nov 5, 2026 • 56min

Dr. Jamie Hardy: Your Business Is Growing. Why Are You Falling Apart? (#592)

Send us Fan Mail“It’s all going to work out and work out for the good.” -Dr Jamie HardyExclusive Insights from This Week's EpisodesYour business can grow while your health, judgment, and leadership quietly deteriorate. Dr. Jamie Hardy reveals how founder depletion spreads into decisions, teams, and performance. Listen before your new normal becomes expensive.Episode Highlights[00:07:36] The health scare that exposed what professional success had been hiding[00:15:35] Why founder depletion affects your family, team, creativity, and work quality[00:20:31] The dangerous founder habit of postponing health until after the next milestone[00:31:53] Why chronic unresolved stress quietly pushes strategic thinking into the backseat[00:36:53] The physical and behavioral warning signs founders often accept as normal[00:39:47] Why fixing the individual fails when the company culture keeps creating depletion[00:46:23] How the first 60 minutes of your day can stop other people's urgency from controlling youFull show notes, transcript, and resources for this episode:https://podcast.deepwealth.com/592The Deep Wealth PodcastMost 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 MasteryThis 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 lifeOne 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.
undefined
Nov 3, 2026 • 1h 4min

Investor Matthew Le Merle Backed 80 Unicorns. This Is What Founders Get Wrong About Fundraising (#591)

Send us Fan Mail“When you have choices, put happiness at the top of your list.” -Matthew Le MerleExclusive Insights from This Week's EpisodesMost founders sell investors on their product while forgetting what investors actually need to hear. Investor Matthew Le Merle reveals the fundraising blind spots that trigger a no, what must happen in the first minute, and how to flip the conversation.Episode Highlights[00:24:14] Why great founders and teams are only the beginning of an investable story[00:27:00] The fundraising blind spot: founders explain the product but forget how investors make money[00:28:00] Why fundraising is about the investor, not the entrepreneur asking for capital[00:29:00] Investors are looking for reasons to say no before most founders finish their pitch[00:29:45] The first-minute test that can turn investor resistance into attention[00:39:27] Why the quality of investors becomes a major differentiator as companies scale[00:55:48] Why a powerful founder vision still needs to fit a five-to-ten-year investment horizonFull show notes, transcript, and resources for this episode:https://podcast.deepwealth.com/591The Deep Wealth PodcastMost 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 MasteryThis 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 lifeOne 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.
undefined
Oct 29, 2026 • 56min

Exit Strategist Cindy Jennings On The Exit That Leaves You Rich But Life Poor & What To Do (#590)

Send us Fan Mail“Have more fun.” -Cindy JenningsExclusive Insights from This Week's EpisodesA great exit can still leave a founder rich but life poor. Exit Strategist Cindy Jennings reveals why freedom without direction becomes drift, and how preparing for life after the deal changes decisions today.Episode Highlights[00:08:40] Why sudden freedom after an exit can become a founder’s free fall[00:12:18] The question founders rarely ask while chasing the biggest possible exit[00:19:18] Why a 10 to 20 year horizon can change the decisions you make today[00:28:41] The three things founders still need when the business no longer structures their life[00:35:47] Why founders romanticize post-exit freedom and underestimate the difficulty of transition[00:39:25] How freedom without direction turns into drift after the business is gone[00:45:56] Why your spouse may experience as much post-exit anxiety as you doFull show notes, transcript, and resources for this episode:https://podcast.deepwealth.com/590The Deep Wealth PodcastMost 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 MasteryThis 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 lifeOne 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.
undefined
Oct 27, 2026 • 41min

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 WooExclusive Insights from This Week's EpisodesYour 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 generalistsFull show notes, transcript, and resources for this episode:https://podcast.deepwealth.com/589The Deep Wealth PodcastMost 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 MasteryThis 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 lifeOne 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.
undefined
Oct 22, 2026 • 51min

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 CeccantiExclusive Insights from This Week's EpisodesYour 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 losesFull show notes, transcript, and resources for this episode:https://podcast.deepwealth.com/588The Deep Wealth PodcastMost 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 MasteryThis 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 lifeOne 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.
undefined
Oct 20, 2026 • 49min

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 MiletichExclusive Insights from This Week's EpisodesLiving 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 inputsFull show notes, transcript, and resources for this episode:https://podcast.deepwealth.com/587The Deep Wealth PodcastMost 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 MasteryThis 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 lifeOne 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.
undefined
Oct 15, 2026 • 50min

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

Send us Fan Mail“Keep going.” -Etinosa AgbonlahorExclusive Insights from This Week's EpisodesYour 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 profitabilityFull 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/B0DNRTKSLHThe Deep Wealth PodcastMost 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 MasteryThis 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 lifeOne 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.
undefined
Oct 13, 2026 • 53min

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

Send us Fan Mail“There are no mistakes, keep doing it.” -Kyle HulsebusExclusive Insights from This Week's EpisodesYour 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 relationshipsFull show notes, transcript, and resources for this episode:https://podcast.deepwealth.com/585The Deep Wealth PodcastMost 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 MasteryThis 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 lifeOne 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.
undefined
Oct 8, 2026 • 57min

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 FinemanExclusive Insights from This Week's EpisodesEveryone 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 moveFull show notes, transcript, and resources for this episode:https://podcast.deepwealth.com/584The Deep Wealth PodcastMost 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 MasteryThis 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 lifeOne 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.
undefined
Oct 6, 2026 • 52min

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 PutraExclusive Insights from This Week's EpisodesYour 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 payFull show notes, transcript, and resources for this episode:https://podcast.deepwealth.com/583https://podcast.deepwealth.com/252The Deep Wealth PodcastMost 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 MasteryThis 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 lifeOne 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.

The AI-powered Podcast Player

Save insights by tapping your headphones, chat with episodes, discover the best highlights - and more!
App store bannerPlay store banner
Get the app