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