AJ Cassata shares how resilience gets built through real rejection, why most founders stall because they quit too early or keep switching directions, and how a predictable funnel only works when the messaging, offer, and follow-up are disciplined.

AJ Cassata is the founder of Revenue Boost, an outbound agency that helps B2B businesses validate their positioning, generate qualified leads, and turn cold outreach into consistent sales calls without relying on ads or algorithms. 

In this episode, he breaks down the modern outbound stack, where AI personalization actually fits, why close rates collapse when objections stay hidden, and the one principle that ties everything together, you can’t fail if you don’t quit.

Key Topics:

-Lead Flow Is the First Domino in Any Business

-The Messaging Fix That Makes Outbound Finally Work

-Why AI Personalization Replaced “Spray and Pray” Outreach

-The Close Rate Problem Is Usually an Unasked Objection

-Consistency Wins, Quitting Just Looks Like “Pivoting”

01:25 Defining Entrepreneurial Excellence as “Problem-Solving Without Quitting”

03:34 Resilience Isn’t a Trait, It’s a Muscle

04:31 Motivation Comes From “Why” Plus Daily Habits

05:52 Lead Flow Is the First Domino in Business

08:29 Why Having Leads Beats Having a Perfect Product With No Attention

09:22 Messaging Is Half The Battle in Outbound

10:52 Segment First, Then Craft Specific Pain-Point Messaging

13:06 AI-Enabled SDRs and Personalization at Scale

16:18 The Hidden Cost of Hiring Isn’t Salary

17:40 When SDRs Still Make Sense in an AI World

21:20 Fixing a Weak Close Rate Starts With Funnel Truth

23:18 Sales Is Detective Work, Invite The Objection

24:25 Founder-Led Sales Is Non-Negotiable Early

26:06 Getting Better Fast With Coaches and AI Call Review

28:32 Sales Methodologies Share the Same Four Pillars

30:11 Speed and Follow-Up Signal Customer Experience

32:25 Why AJ Started Door-to-Door and Dropped Out

37:49 The Pivot Into Digital Marketing and First Clients

38:29 Building an Agency From a Sprinter Van

39:24 The Vietnam Move and Making Remote Work Sustainable

42:03 Constraints Breed Creativity in Remote Hiring and Selling

46:02 Marketing Fundamentals Before Channels

47:41 The Three Online Lead Engines Explained

50:33 Minimum Viable Online Presence for Trust

52:10 Outbound Now, Inbound Next for Compounding

54:09 The Growth Ceiling Is Usually Operations

56:38 The One Outbound Tool AJ Would Keep

57:12 Cold Email Isn’t Dead, Bad Cold Email Is

58:03 Cold Calling Still Works, Maybe Better Now

59:35 The One Book Every Founder Should Read on Offers

01:00:42 The Single Metric AJ Tracks Closest to Revenue

01:01:06 Advice to His 19-Year-Old Self

01:02:07 The One Rule That Ties It All Together

Connect with -AJ Cassata:

LinkedIn - linkedin.com/in/ajcassata

Website: revenueboost.net/

facebook.com/groups/b2bsalesandmarketingsecrets

Connect to Entrepreneurial-Excellence Podcast:

LinkedIn - https://www.linkedin.com/company/entrepreneurial-excellence-podcast

Youtube - http://www.youtube.com/@EntrepreneurialExcellencePod

TikTok - https://www.tiktok.com/@eepodcast24

Facebook - https://www.facebook.com/profile.php?id=61570329516959

Website - https://www.levy.company/entrepreneurial-excellence

Nick Mehta breaks down how committing to a real problem before a category exists can shape an entire industry, why founders get stuck at scale, and the mindset shifts required to build something that lasts.

Nick Mehta is the Co-Founder and CEO of Gainsight, one of the companies that helped define Customer Success as a core business function. In this episode, he shares hard-earned lessons on founder growth, hiring beyond yourself, stepping back at the right time, and why entrepreneurial excellence has nothing to do with hype and everything to do with long-term conviction.

Key Topics:

- Why Most Founders Never Reach Real Excellence

-The Risky Bet That Built a Category From Nothing

-When Stepping Back as CEO Is the Smartest Move

-The Hiring Mistake That Quietly Kills Scale

-Why Passion Comes After Mastery, Not Before

01:14 Defining Entrepreneurial Excellence Beyond Exits and Valuations

02:38 Why Putting Your Whole Heart In Matters More Than Outcomes

03:39 The Litmus Test That Reveals Who’s Truly Committed

05:18 How Great Founders Stay Sane Without Losing Intensity

06:32 Burnout, Dopamine, and Why Stepping Away Makes You Better

08:17 Why Market Choice Matters More Than Culture or Work Ethic

How picking the right space quietly determines long-term success.

09:41 The “10-Year Overnight Success” Myth Explained

10:11 Why Nick Joined a No-Revenue Company in a Non-Existent Category

11:09 How Customer Success Became a Category, Not a Feature

The early insight that turned churn into a board-level priority.

13:00 Why Founders Stepping Back Can Be a Strength, Not a Failure

15:00 From Extreme Shyness to CEO Presence

18:01 Why Childhood Patterns Shape Leadership Style

20:08 Self-Awareness, Coaching, and the Enneagram for CEOs

23:06 What Investors Optimize For vs. What Founders Should

25:29 How to Filter Advice Without Getting Starstruck

27:47 Why Nick Chose Operating Over Venture Capital

29:35 Why “Follow Your Passion” Is Often Bad Advice

32:05 How Getting Good at Something Creates Passion Over Time

34:09 How Family Sacrifice and Regret Shaped Entrepreneurial Drive

36:28 Choosing the Wrong Path First—and Correcting It

38:09 How Gainsight Built a Category Through Community First

39:41 The Accidental Meetup That Sparked a Movement

42:30 Why Community Became a Durable Competitive Advantage

43:22 Why Founders Shouldn’t “Scale Themselves Out” Too Early

44:57 Being a “Micro-Learner,” Not a Micromanager

46:25 The One Decision That Kills Companies Quietly

48:40 How to Avoid Shiny Object Syndrome as a CEO

50:34 What Real Company Culture Actually Is

53:27 “Human First” as a Competitive Advantage

54:23 Why Speed Is the New Differentiator in SaaS

56:21 The Hidden Cost of Over-Protecting Employees

58:03 When CEO Involvement Becomes a Bottleneck

59:20 Where Founders Should Actually Micromanage

01:00:22 Why Delegation Isn’t About Time, It’s About Context

01:02:03 The Brewery Lesson Every Founder Should Learn

01:03:25 What a “Founder-Only” Company Really Looks Like

01:05:36 Why Hiring Is More Expensive Than Founders Think

01:07:02 Why Investor Advice Often Doesn’t Apply

Connect with - Nick Mehta:

LinkedIn - linkedin.com/in/nickmehta

Connect to Entrepreneurial-Excellence Podcast:

LinkedIn - https://www.linkedin.com/company/entrepreneurial-excellence-podcast

Youtube - http://www.youtube.com/@EntrepreneurialExcellencePod

TikTok - https://www.tiktok.com/@eepodcast24

Facebook - https://www.facebook.com/profile.php?id=61570329516959

Website - https://www.levy.company/entrepreneurial-excellence

In this episode, Scott Kelly, Founder and CEO of Black Dog Ventures, shares what actually separates founders who build real companies from those who stay stuck chasing capital. He talks openly about why fundraising is often mistaken for progress, why execution beats ideas every time, and why many startups fail not because of the market—but because founders don’t know when to let go, delegate, and lead.

Scott breaks down what investors really look for, how trust is built long before money is involved, and why consistent momentum matters more than a perfect plan. He explains how strong teams are formed, why most founders underestimate the cost of doing everything themselves, and how small wins every two weeks compound into real traction. 

As technology makes it easier for anyone to build, Scott shares what still creates a true edge: relationships, credibility, and the willingness to keep moving forward when the answer is “no.” 

This conversation pulls back the curtain on venture, leadership, and what entrepreneurial excellence really looks like when the cameras are off.

Key Topics:

- Fundraising as a false signal of entrepreneurial success

- Execution and delegation as the real drivers of scale

- Trust and relationships as the foundation of venture outcomes

- Traction over storytelling in winning investor confidence

- Leadership built on humility, learning, and momentum

Quote  From The Episode:

“Most entrepreneurs shouldn’t be raising money. They should be building their business.”

- Scott Kelly

Timestamp:

[00:20] Fundraising Is a Vanity Metric—and Most Founders Get Excellence Wrong

[11:09] Real Founders Let the Market Decide Instead of Scaling Too Early or Chasing Capital

[20:58] How Relationship Capital Turns Simple Coffee Meetings Into Eight-Figure Deals

[29:58] Trust Is the Ultimate Advantage in Venture—and the Fastest Way to Control Deal Flow

[40:12] Winning Investors Without Raising Money: The Power of Relentless Progress Updates

[50:18] The Founders Who Win Every Two Weeks Obsess Over Time, Delegation, and Speed

[1:01:24] Building Defensible Moats in a World Where AI Makes Everyone Equal

[1:13:25] Outro

Connect with - Scott Kelly:

LinkedIn -  linkedin.com/in/blackdogceo

Websites -blackdogventurepartners.com facebook.com/blackdogventurepartners/

Connect to Entrepreneurial-Excellence Podcast:

LinkedIn - https://www.linkedin.com/company/entrepreneurial-excellence-podcast

Youtube - http://www.youtube.com/@EntrepreneurialExcellencePod

TikTok - https://www.tiktok.com/@eepodcast24

Facebook - https://www.facebook.com/profile.php?id=61570329516959

Website - https://www.levy.company/entrepreneurial-excellence

In this episode, we sit down with a leader who walked away from a $7B role to start again in a kitchen with two young founders. He shares the raw truth about what makes great founders win, why most people who “work hard” never achieve real outcomes, and how to see the world differently when the stakes are high.

We go deep into the moments that shaped billion-dollar fintech moves — including the split-second choice that saved $700M during the SVB meltdown, and the internal mistake that triggered one of the toughest days of his life. 

You’ll hear how he recruits top talent without relying only on money, why curiosity matters only when aimed at the right things, and what it means to truly understand the details that run a business. He also shares the childhood lesson that shaped his leadership style and gave him the courage to ask the questions others avoid.

Tune in to hear the thinking, the risks, and the uncommon moves behind true entrepreneurial excellence.

Key Topics:

- The hidden traits that separate great founders from everyone else

- Real meaning of hard work and why most people get it wrong

- Decisions that saved Brex during high-stakes crisis moments

- Truth about recruiting A players B players and building the right team

- Mindset shift needed to grow fast and lead through massive change

Quote  From The Episode:

“When something doesn’t make sense, a lot of people are afraid to ask. I don’t have that fear.”

- Michael B. Tannenbaum

Timestamp:

[00:20] Why a $7B CRO Walked Away to Start in a Kitchen — And What He Learned About Founders Who Win

[11:04] The Harsh Truth About “Hard Work” — And Why Most People Never Produce Real Outcomes

[20:05] How Brex Survived the SVB Meltdown—And the One Decision That Saved $700 Million

[30:41] Inside the Decision That Nearly Broke Brex—And the Leadership Blind Spot No One Saw Coming

[41:28] The Childhood Lesson That Turned a CFO’s Son Into One of FinTech’s Boldest Leaders

[52:50] Outro

Connect with - Michael B. Tannenbaum:

LinkedIn - linkedin.com/in/michaeltannenbaum

Website - www.figure.com

Connect to Entrepreneurial-Excellence Podcast:

LinkedIn - https://www.linkedin.com/company/entrepreneurial-excellence-podcast

Youtube - http://www.youtube.com/@EntrepreneurialExcellencePod

TikTok - https://www.tiktok.com/@eepodcast24

Facebook - https://www.facebook.com/profile.php?id=61570329516959

Website - https://www.levy.company/entrepreneurial-excellence

In this episode, we sit down with Tyler Wagner, a college dropout who built an eight-figure business by doing the opposite of what most founders do. From risking everything at 20 years old to helping nearly 5,000 authors turn their ideas into influence, Tyler shares the raw truth behind failure, focus, partnerships, and the real value of writing a book in the AI age.

Tyler opens up about the mindset shift that changed his life, why he ran toward failure instead of avoiding it, and how he turned one book into a multi-million-dollar company. He talks about ego, legacy, freedom, and the lonely part of reaching “success” that no one prepares you for. 

He also breaks down why partnerships beat ads, why most entrepreneurs quit too early, and why many founders still fear writing their first book.

Tune in to learn the shifts that helped Tyler turn one book into an empire—and how you can shift your journey too.

Key Topics:

-The mindset shift that turns failure into a pathway to success

-How writing a book becomes a real tool for influence and credibility

-Why partnerships outperform ads for long-term business growth

-The hidden challenges of reaching time freedom as an entrepreneur

-The ego, legacy, and emotional drivers behind why founders publish books

Quote  From The Episode:

“I actually like failure, because the more I fail, the closer I know I am to succeeding.”

- Tyler Wagner

Timestamp:

[00:20] The Mindset Shift That Turns Dropouts Into Industry Leaders

[12:15] How a 20-Year-Old Bestseller Exposed the Secret Value of Publishing

[23:13] How Entrepreneurs Turn a $50K Book Into a Seven-Figure Funnel

[34:40] How a College Dropout Scaled to Eight Figures by Doing the Opposite of Everyone Else

[45:59] Conferences vs. Digital: The Surprising Truth About Where Real Relationships Are Built Today

[56:38] How AI Is Quietly Killing Ghostwriting as We Know It

[1:08:34] Why Partnerships Beat Ads, Content, and Virality—Every. Single. Time.

[1:14:30] Outro

Connect with - Tyler Wagner:

LinkedIn - linkedin.com/in/tylerbwagner

Website - authorsunite.com/

partnerprofits.io

Connect to Entrepreneurial-Excellence Podcast:

LinkedIn - https://www.linkedin.com/company/entrepreneurial-excellence-podcast

Youtube - http://www.youtube.com/@EntrepreneurialExcellencePod

TikTok - https://www.tiktok.com/@eepodcast24

Facebook - https://www.facebook.com/profile.php?id=61570329516959

Website - https://www.levy.company/entrepreneurial-excellence

In this episode, we go inside the real mind of a founder with Jason Johnson — the builder behind August smart locks and now CEO of DOMA. Jason shares what most people never hear: why founders burn out, why teams break, why distribution kills more startups than bad ideas, and why you must protect your time like your life depends on it.

He talks openly about losing a company at 29, rebuilding himself at Dolby, firing fast, trusting his gut, and giving his team radical responsibility. Jason also explains why small teams win, why outsourcing is the future, and why believing in yourself is not a motivational quote — it’s survival.

Tune in to hear the truth about failure, hunger, and why your toughest years might be your edge.

Key Topics:

-Radical ownership and fast decision making

-The real cost of mis-hiring and early firing

-Why small teams outperform large organizations

-Outsourcing as a strategic edge for modern founders

-The mindset required to survive repeated failure

Quote  From The Episode:

“You have to radically believe in yourself.”

- Jason Johnson

Timestamp:

[00:19] The One Skill Every Founder Needs—but Almost No One Talks About

[11:07] Why the Best Founders Win Before They Even Build the Product

[21:11] The Practice Habit That Separates Average Founders from Icons

[31:11] The Brutal Truth About Why Founders Quit—and Why Jason Johnson Never Did

[41:19] The Outsourcing Rule Founders Ignore—and It’s Wasting Their Time

[50:31] The New Blueprint: Why the Future Belongs to Tiny Teams

[1:00:25] The Hardest Decision Founders Avoid—And Why It Destroys Their Companies

[1:06:32] Outro

Connect with - Jason Johnson:

LinkedIn -  linkedin.com/in/jcjohnson

Connect to Entrepreneurial-Excellence Podcast:

LinkedIn - https://www.linkedin.com/company/entrepreneurial-excellence-podcast

Youtube - http://www.youtube.com/@EntrepreneurialExcellencePod

TikTok - https://www.tiktok.com/@eepodcast24

Facebook - https://www.facebook.com/profile.php?id=61570329516959

Website - https://www.levy.company/entrepreneurial-excellence

In this episode, Adam sits down with Mitch Joel — one of the sharpest minds in business, storytelling, and the future of work — for a conversation that exposes the real truths about entrepreneurship.

Mitch shares powerful insights from decades of interviewing top thinkers, building companies, and staying ahead in a world that never stops shifting. He breaks down why success is the anomaly, why most founders fail long before their idea does, and how “the market is brutal” in ways people rarely talk about. 

We go deep into the things most leaders avoid:

why fear can become a superpower, how timing shapes outcomes more than talent, why your network is your net worth, and what it really takes to stay curious when everyone else gets comfortable. Mitch also reveals how AI changes the game, why many people will get left behind, and how to protect your edge when the world moves faster than your habits.

🎧Tune in — this conversation might be the unlock you didn’t know you needed.

Key Topics:

- Mindset shift from speed to direction and momentum

- Real value of storytelling and why most founders overlook it

- Power of nuance when finding product fit and evolving a message

- Truth about delegation and knowing when you’re the bottleneck

- Rise of AI and how curiosity becomes a competitive advantage

Quote From The Episode: 

“Most people won’t do it. And that’s the opportunity.”

- Mitch Joel

Timestamp:

[00:16] Why Only a Few People Actually Win in Business

[18:20] Timing Will Make or Break You—And You Can’t Control It

[29:13] The Hidden Reason Your Brand Gets Ignored

[40:17] The Tiny Discipline That Builds Million-Dollar Networks

[54:13] The Silent Trap That Destroys Early-Stage Startups

[1:07:51] Most Founders Fail Because They Can’t Let Go

[1:19:23] Your Network Is Your Net Worth (But Almost No One Acts Like It)

[1:34:18] Outro

Connect with - Mitch Joel:

LinkedIn - linkedin.com/in/mitchjoel

Website - mitchjoel.com

sixpixels.com

thinkersone.com

Connect to Entrepreneurial-Excellence Podcast:

LinkedIn - https://www.linkedin.com/company/entrepreneurial-excellence-podcast

Youtube - http://www.youtube.com/@EntrepreneurialExcellencePod

TikTok - https://www.tiktok.com/@eepodcast24

Facebook - https://www.facebook.com/profile.php?id=61570329516959

Website - https://www.levy.company/entrepreneurial-excellence

What if everything you believe about “great customer service” is actually wrong?

In this episode, we sit down with Rick DeLisi — a 20-year expert on customer experience, bestselling author of The Effortless Experience, and lead researcher behind a landmark study on how over 1,000 business leaders are using AI in customer service.

Rick breaks down why real customer loyalty has nothing to do with delight, fancy gestures, or “wow moments.” It comes from something far simpler — making people feel smart for choosing you and giving them an experience that feels way easier than expected. 

We also dive into how the next generation of AI will reshape support, why replacing humans is the wrong move, and how the best companies create a balance between automation and human connection. 

Tune in to learn the hidden psychology behind effortless experiences and why it’s the real edge every founder needs right now.

Key Topics:

-How effortless experiences build real customer loyalty

-Why thinking like your customers changes everything

-The new empathy that creates faster and better solutions

-How AI and humans should work together in customer service

-The leadership mindset that keeps companies truly customer centric

Quote  From The Episode:

“Entrepreneurial excellence is thinking like your customers, not about them”

- Rick DeLisi

Timestamp:

[00:20] Why Most Leaders Are Flying Blind — And Don’t Even Know It

[11:16] The Hidden Habit That Destroys Customer Loyalty Overnight

[22:30] The Psychology Trick That Turns Angry Customers Into Lifelong Fans

[33:54] The Fatal Mistake Companies Make When ‘Fixing’ Customer Problems

[45:28] AI Won’t Save You—But This One Shift Will Transform Your Customer Experience

[55:54] The New Empathy: Why ‘I’m Sorry’ Is Killing Your Customer Experience

[1:07:02] Why Employee Effort Is the Hidden Metric That Predicts Customer Loyalty

[1:27:30] Outro

Connect with - Rick DeLisi:

LinkedIn -  linkedin.com/in/rick-delisi-1122257

Website - glia.com

Email: [email protected]

Connect to Entrepreneurial-Excellence Podcast:

LinkedIn - https://www.linkedin.com/company/entrepreneurial-excellence-podcast

Youtube - http://www.youtube.com/@EntrepreneurialExcellencePod

TikTok - https://www.tiktok.com/@eepodcast24

Facebook - https://www.facebook.com/profile.php?id=61570329516959

Website - https://www.levy.company/entrepreneurial-excellence

In this episode, investor and ecosystem builder David Fogel reveals what he’s learned from working with over a thousand founders across the globe — the wins, the failures, and the tough lessons that define true entrepreneurial excellence.

David shares why most startups fail long before they run out of money, how founders can learn to adapt fast, and why falling in love with your problem matters more than falling in love with your product. He opens up about the mission behind Alma Angels, a $1 trillion movement backing women founders, and the hidden biases still shaping the world of venture capital.

If you’re a founder, investor, or leader searching for what it really takes to build something that lasts, this conversation will change the way you see success.

🎧 Tune in to discover how great founders turn pain into progress, why self-awareness beats perfection, and what it truly means to play the infinite game in business and life.

Key Topics:

-Why problem obsession matters more than product obsession

-How bias and warm intros shape who actually gets funded

-Building companies not just products as you scale

-Choosing and stress testing the right co founder

-Leading with empathy while making hard decisions

Quote From The Episode: 

“Pain is learning — the difference between a good entrepreneur and an excellent one is their willingness to feel it.”

-David Fogel

Timestamp:

[00:19] The Hidden Truth Behind Why Startups Fail — And How Great Founders Turn It Around

[12:13] The Unspoken Truth About Bias, Power, and the $1 Trillion Mission to Back Women Founders

[24:41] Inside the $1 Trillion Network Powering the Next Generation of Women Founders

[33:48] The One Trait That Separates Great Founders From Everyone Else

[44:43] Warm Intros, Cold Truths: How Great Founders Turn “No” Into Momentum—and Guard Their Time

[53:50] How to Choose the Right Co-Founder—Before It’s Too Late

[1:04:46] Why the Best Leaders Make Tough Calls—with Heart

[1:18:36] Outro

Connect with - David Fogel:

LinkedIn - linkedin.com/in/fogeldavid

Website - alma-angels.com/

Connect to Entrepreneurial-Excellence Podcast:

LinkedIn - https://www.linkedin.com/company/entrepreneurial-excellence-podcast

Youtube - http://www.youtube.com/@EntrepreneurialExcellencePod

TikTok - https://www.tiktok.com/@eepodcast24

Facebook - https://www.facebook.com/profile.php?id=61570329516959

Website - https://www.levy.company/entrepreneurial-excellence

In this episode, Kasim Aslam reveals the 7 Steps to true entrepreneurial greatness. From running 17 companies to hiring rockstars instead of babysitters, Kasim exposes the uncomfortable truth behind why most leaders will never scale — they don’t trust anyone but themselves. This isn’t another “delegate better” talk. It’s a full mindset teardown. 

Kasim walks us through The Black Box of Delegation — a system that turns chaos into clarity, builds ownership instead of oversight, and frees you to work on what actually compounds. He explains why paying 10% more gets you 100x results, how the wrong kind of “management” kills top talent, and why mediocrity is the default setting for most modern businesses.

🎧 Tune in if you’re ready to stop working in your business and start architecting the people, systems, and leverage that make it unstoppable.

Key Topics:

-The Black Box of Delegation

-Why Overpaying Attracts 100x Talent

-Building Leverage Through People, Not Processes

-Escaping the Trap of Mediocre Leadership

-The Founder’s Shift from Control to Clarity

Quote  From The Episode: 

“I believe every human is a miracle.”

-Kasim Aslam

Timestamp:

[00:20] Why Most “Entrepreneurs” Aren’t Actually Entrepreneurs

[14:17] The Only Skill That Matters in a Post-AI World

[23:04] The 7 Secrets to Hiring Talent That Changes Everything

[32:52] The Real Reason Your Team Isn’t World-Class Yet

[42:21] The Black Box of Delegation: How to Let Go Without Losing Control

[51:50] Traffic First. Talent Next. Scale.

[1:04:51] Build Authority Or Be Invisible

[1:25:17] Outro

Connect with - Kasim Aslam:

LinkedIn - linkedin.com/in/kasimaslam

Website - ParetoTalent.com

Connect to Entrepreneurial-Excellence Podcast:

LinkedIn - https://www.linkedin.com/company/entrepreneurial-excellence-podcast

Youtube - http://www.youtube.com/@EntrepreneurialExcellencePod

TikTok - https://www.tiktok.com/@eepodcast24

Facebook - https://www.facebook.com/profile.php?id=61570329516959

Website - https://www.levy.company/entrepreneurial-excellence