Best Bootstrapper Podcasts (2025)

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Mastering the 3 Conversions: A Strategy for Bootstrappers 1:22:51

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17d ago1:22:51

1:22:51

Starting a business without outside funding is both challenging and rewarding—but knowing how to navigate the leap from idea to success is critical. Many entrepreneurs struggle with the transition from scrappy beginnings to sustainable growth, often focusing on the wrong milestones or failing to optimize their resources. This session, led by season…

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The Bootstrapper's Guide to Account-Based Marketing That Actually Works 37:00

19d ago37:00

37:00

Most businesses waste thousands on complex account-based marketing (ABM) programs that never deliver results. But what if you could build a high-performing ABM system without the hefty price tag? Marketing leader Mason Cosby reveals how he generated over $15 million in the past three years using a scrappy approach to account-based marketing. Throug…

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HOW NOT TO QUIT ON A DREAM! 1:06:31

24d ago1:06:31

1:06:31

Send us a text Norman Towns on Outworking the Odds Let’s be real, success isn’t sexy at the start. Norman Towns knows that better than anyone. Before he hit the screen, he was doing all the jobs no one brags about: spinning signs on the sidewalk, washing dishes, pulling overnight security shifts. Whatever it took. In this episode, Norman keeps it r…

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#152: Practical SaaS CEO Stays On After 100% Cash Sale - Tracy Larson 1:04:10

3d ago1:04:10

1:04:10

Tracy Larson is President and CEO of WeSuite, a vertical sales automation platform designed for larger integrators who sell complete security systems for commercial and residential real estate. Tracy and the cofounders were in the security systems business before launching a sales software company for this market in 2008. WeSuite is now a comprehen…

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Your Marketing Budget is Going to the Wrong Place 35:19

4d ago35:19

35:19

Your next big revenue boost won't come from another expensive lead generation campaign. It's sitting right there in your customer database. Marketing veteran David Baer pulls back the curtain on why most businesses hemorrhage profits by fixating on new leads while neglecting their goldmine of existing customers. With hard-won insights from Broadway…

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#151: Facial Recognition SaaS for Casinos to Almost $10M in Revenue – Henry Valentino 1:02:52

10d ago1:02:52

1:02:52

Henry Valentino is the founder and CEO of EConnect, a leading provider of facial recognition software for casinos and stadiums, ensuring venue security and compliance. He founded EConnect in 2009 and pivoted several times before focusing on a security platform utilizing AI for casinos during the COVID-19 pandemic. The Econnect platform offers facia…

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The 3-Step Framework for Finding Lost Revenue in Your Business 39:21

12d ago39:21

39:21

Most business owners walk past thousands in potential revenue every single day without realizing it. In this eye-opening episode, experienced entrepreneur Emylee Williams reveals her proven "Chase the Breadcrumbs" methodology for uncovering significant hidden revenue in your existing business. After co-founding and running a multi-million dollar ma…

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Top 7 Pitfalls When Using AI in Your Business: And Tips for Using AI More Effectively 1:24:43

17d ago1:24:43

1:24:43

AI is a powerful tool, but it’s not a silver bullet. Many entrepreneurs get caught up in the allure of automation and data-driven decision-making, only to realize that AI is just a technology—not a comprehensive business strategy. When used correctly, AI can streamline operations, improve efficiency, and enhance customer experiences, but overconfid…

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#150: Grew an Unsexy Small Software Biz Into a SaaS Powerhouse - Josh Turley 1:16:36

18d ago1:16:36

1:16:36

Josh Turley is CEO of RTA Fleet Management, a fleet management software company that his grandfather started in the 1980’s and ran as a small family business for decades. Then Josh’s father ran the business until 2015, never growing this slow, old-school business past $2 million in revenues. Josh had worked in the business before, but in 2016, Josh…

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#149: How Partner-Led Sales Built A $7M Bootstrap SaaS Business - Sameer Narkar 1:03:58

25d ago1:03:58

1:03:58

Sameer Narkar is the founder and CEO of Konnect Insights, a global SaaS company based in Mumbai that provides an omnichannel customer experience platform to consumer brands in 100 countries. Sameer created Konnect Insights in 2015 to help customer service teams respond to customers who mention their brands on social media. The product and company h…

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How Giving Away Free Gym Memberships Led to Multi-Million-Dollar Success 33:53

26d ago33:53

33:53

Most 12-year-olds make pocket money doing chores. Craig Schulze was different - he engineered a way to earn $25 per hour making gift boxes in the early 90s. That entrepreneurial spirit launched him into a 25-year journey building multiple successful businesses across the globe. In this value-packed episode, Craig shares hard-won wisdom from his exp…

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#148: These Bootstrappers Sold Modern Digital LeadGen to Conservative German Businesses - Chris Erler 55:44

1M ago55:44

55:44

Chris Erler was co-founder and COO of ComX, a sales pipeline generation for mid-market B2B companies in Germany and Europe. Chris and two other founders started the company in 2018 to conduct turnkey modern digital marketing and lead generation solutions for traditional German companies. As a tech-enabled service that combines technology, data, and…

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Get More Local Customers Now with Smart Google Profile Strategies 33:32

1M ago33:32

33:32

The difference between thriving local businesses and those that struggle often comes down to their Google presence. Marketing expert Rita Suzanne pulls back the curtain on proven strategies to dominate local search and attract more customers. Rita walks through the essential elements of an optimized Google Business Profile, including: Multiple cate…

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#147: How a Philadelphia Insurance Agent Built the Uber of Surety Bonds - Aaron Steffey 1:04:44

1M ago1:04:44

1:04:44

Aaron Steffey is the co-founder and co-CEO of Propeller, an online platform that enables insurance agents and brokers to issue surety bonds instantly — without the lengthy paperwork or back-and-forth typically involved in bonding. Aaron was an insurance agent, and his co-founder cousin, Chris, was a surety bond underwriter before 2019, when they se…

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Marketing Lessons from The Most Controversial Brand in History 49:03

1M ago49:03

49:03

The single most cost-effective marketing campaign in history turned $66 million into $5.9 billion in free media exposure. While many business owners let personal feelings block them from game-changing strategies, today's guest rips open the psychology behind 47 of Trump's battle-tested marketing techniques. Jack Turk, former head copywriter for Dan…

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#146: This European SaaS Bootstrapper Raised $22M in Growth Equity Without Losing Control - Roy van den Broek 1:00:46

2M ago1:00:46

1:00:46

Roy van den Broek is the founder and CEO of Rentman, a rental business management software platform for event and media production companies. Roy built software for his event equipment rental business in the Netherlands. He had over 100 software customers in Europe before selling his rental equipment company in 2015 to focus on growing his Rentman …

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The Unconventional Marketing Secrets That Generated $100K in Free Exposure 38:06

2M ago38:06

38:06

Most business owners waste thousands on marketing that gets ignored. Nathan Baws takes a different approach - using creative stunts and viral campaigns to generate massive exposure without spending a dime. From walking across London's Tower Bridge wearing handwritten signs to leveraging "ugly" marketing that cuts through the noise, Nathan shares th…

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#145: Making Big Bold Bets with Patient Execution as a Bootstrapped Founder - Gopal Krishnamurthy 59:50

2M ago59:50

59:50

Gopal Krishnamurthy is the founder and CEO of Lumel, which has a suite of products focused on enterprise performance management (EPM). Their apps allow users to plan, report, and analyze data using the modern native app framework vs. traditional SaaS on top of modern cloud data platforms such as Microsoft Fabric, Snowflake, Databricks, and others. …

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How This Entrepreneur Made $500K Last Year While Only Working 10 Hours A Week 32:53

2M ago32:53

32:53

A failed multi-million dollar business. The loss of a child and a father. Most entrepreneurs would crumble under such devastating blows. But Rob Lee used these painful experiences to completely reinvent his approach to business using AI. Today Rob runs a thriving agency working just 10 hours per week with a small staff of three, generating over $50…

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#144: From Founder-Led Sales to Scalable Go-To-Market in Vertical SaaS - Phil Stern 58:20

2M ago58:20

58:20

Phil Stern is the operating principal of Mainsail Partners, a growth equity firm that invests in bootstrapped vertical SaaS companies. Mainsail offers deep operating support to the leaders in their portfolio companies to help them grow more efficiently. Phil leads the GTM operations team, helping their founders scale sales, marketing, and success t…

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What Dogs Taught Me About Growing a 7-Figure Business 35:49

2M ago35:49

35:49

Dog boarding entrepreneur Erin Schnute never planned to build a thriving pet care business. But after stumbling into pet sitting as a side gig, she discovered powerful leadership principles by observing pack dynamics. Today, her company Bed & Barkfest commands premium rates while maintaining a waitlist of eager clients. In this candid conversation,…

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How to Start a Business (Even If You're Scared Sh*tless) 7:57

2M ago7:57

7:57

Send us a text Starting a small business from scratch? Learn how to launch with no money, no connections, no fluff. Ever feel like most business advice is just recycled guru nonsense or comes from people born wealthy? This episode is for the real ones—those starting small businesses without money, privilege, or fancy degrees. This episode kicks off…

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#143: From Professional Services to a $30M SaaS Business with a PE Acquisition - Sean Hoban 1:04:53

2M ago1:04:53

1:04:53

Sean Hoban was co-founder and former CEO of Kimble Applications, a leading professional services automation (PSA) software for organizations to manage their professional services business's entire operational and financial lifecycle. Sean and his co-founders had already started, grown, and sold a pro services organization before creating a PSA prod…

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The "Lazy" Way to Double Your Sales Without New Lead Generation 38:24

2M ago38:24

38:24

Businesses spend thousands chasing new leads while ignoring their most valuable asset - their existing customer database. Digital marketing expert Jay Vics pulls back the curtain on proven strategies to reactivate these dormant contacts and turn them into sales. Through real-world examples, Jay demonstrates how retail and service businesses can: Ex…

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Growing a hosting platform to $400k ARR: Elston Baretto (Tiiny Host) 52:30

2M ago52:30

52:30

After a hiatus, The Ramen Club podcast (formerly Ramen FM) is back! For episode 10, I spoke to my good friend friend and long-time Ramen Club member, Elston Baretto (founder of Tiiny Host). Tiiny Host is the simplest way to host and share your work online - uploading HTML, PHP, PDFs & Zip files (plus more soon) in seconds. Started 4 years ago, Elst…

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#142: Why This 3x SaaS Founder Couldn't Stay Retired to Launch His New Al Startup - Josh LaSov 58:37

2M ago58:37

58:37

Josh LaSov is the founder and former CEO of Satori Reporting, an advanced reporting and business intelligence (BI) solution for mid-market businesses that use NetSuite financial software. Satori provided pre-built reports and dashboards, a tailored data warehouse, and detailed data models that leveraged the popular Power BI software. Josh launched …

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Why Most Small Businesses Fail Within 2 Years (And How to Beat the Odds) 28:46

2M ago28:46

28:46

90% of small businesses fail within their first two years. But it's not because their product is bad or they aren't working hard enough. Business coach Tammy Johnston reveals the real reasons behind these failures and the practical solutions that can help new businesses thrive. With over 32 years of experience working with small business owners, Jo…

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#141: Inside Acquire.com's Process for Selling Sub-$5M SaaS Companies - Andrew Gazdecki 55:39

3M ago55:39

55:39

Andrew Gazdecki is the founder and CEO of Acquire.com, a marketplace of buyers and sellers of smaller, profitable SaaS products with revenues between $100,000 and $5,000,000. Andrew sold his own software company and learned how little support and information was available to sell a software product for under $5-10 million in deal size. Acquire.com …

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Smart Ways To Test Direct Mail Without Breaking The Bank 39:23

3M ago39:23

39:23

Digital marketing costs are soaring while response rates plummet. Smart businesses are rediscovering an overlooked marketing channel that's delivering massive returns - direct mail. In this powerful episode, direct mail expert David Foley reveals his proven system for testing direct mail campaigns with as few as 400 customers. You'll discover: A si…

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#140: The Anti-Silicon Valley Playbook: How Genius Monkey Built a $100M Ad Tech Business on Their Own Terms - Seth Hassell and Clint Ethington 1:04:34

3M ago1:04:34

1:04:34

Seth Hassell and Clint Ethington are the co-founders of Genius Monkey, a programmatic ad tech platform with proven targeting, tracking, and attribution for optimized results. Seth and Clint were childhood friends who worked on many business ventures before launching Genius Monkey in 2009, leveraging their experience in digital ad technologies. Geni…

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Why Your Money Mindset Matters More Than Your Strategy 47:46

3M ago47:46

47:46

At 23, Michelle Jacobik maxed out her credit cards and turned to payday loans while working at a financial services firm. The irony wasn't lost on her. Today, after building and selling a $12M insurance agency, she helps entrepreneurs avoid the financial pitfalls that almost ended her own business dreams. In this candid discussion, Michelle reveals…

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#139: Bootstrapped Founder is Getting Ready for the AI Wave at $20M ARR - Shalin Jain 1:07:35

3M ago1:07:35

1:07:35

Shalin Jain is the founder and CEO of HappyFox, a successful bootstrapped company that provides modern help desk management software for customer service, support, and IT management organizations. Shalin and his small team in India built many successful products from 2000-2010, then focused on HappyFox and moved to the US in 2011. HappyFox is a mid…

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Making Money by Being Authentically You 35:16

3M ago35:16

35:16

Rob Anspach transformed his struggling carpet cleaning business into a thriving enterprise by doing the opposite of his competitors - giving away free services. This counter-intuitive approach led to his average sale increasing from $50 to over $500. Now with 30+ years of entrepreneurial experience and 50 published books under his belt, Rob shares …

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#138: Achieved Strategic Acquisition Just 2 Years After Launch - Brian Kesselman 1:00:15

3M ago1:00:15

1:00:15

Brian Kesselman is cofounder and now CRO of Skematic, a compliance management and workflow software for financial services firms. Brian was a lawyer for major financial services companies who helped manage internal compliance in this highly regulated industry. He took a job selling compliance software and broke sales records before starting Skemati…

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Business Organization From Paper Piles To Digital Files 35:40

3M ago35:40

35:40

Your office clutter is costing you money. Every minute spent searching for documents, every forgotten task, every overwhelmed moment staring at your inbox chips away at your productivity and peace of mind. Certified productive environment specialist Carla Zwaan joins us to share her proven framework for office transformation. After helping entrepre…

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Your Email Marketing Playbook Just Expired And It's Killing Sales 1:13:37

3M ago1:13:37

1:13:37

Your email marketing could be headed for disaster without you even knowing it. In this revealing episode, guest host Dean Mercado interviews certified inbox optimization specialist Scott Hartley, who pulls back the curtain on what's really happening with email deliverability in 2025. Scott shares the four critical metrics every business owner must …

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#137: Her Amazing Story of 0-$30M ARR with No Outside Funding - Rebecca Shostak 1:04:57

4M ago1:04:57

1:04:57

Rebecca Shostak is co-founder and chief brand officer of Flodesk, the popular email marketing software for small businesses that care about beautiful branded emails. After prototyping the product and validating the problem, they launched in 2019 with a viral explosion that still powers their bootstrapped growth. Six years later, Flodesk has over $3…

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The Brain Science Behind Faster Business Growth 38:11

4M ago38:11

38:11

Your business growth may be getting sabotaged by hidden friction points you don't even realize exist. In this episode, award-winning strategist Ryan Chute reveals the biological and psychological barriers blocking your path to rapid scaling. After transforming his own approach from grinding in retail to running a thriving 8-figure agency, Ryan now …

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#136: Practical Founder Has Big Exit and Un-Retires to Build 2nd SaaS Success - Brian Dosal 1:11:26

4M ago1:11:26

1:11:26

Brian Dosal was the founder and CEO of BrightGauge, a software company he bootstrapped and grew to almost $10M ARR with his brother before successfully selling the company in 2019. BrightGauge was a business analytics and dashboard for key metrics for the Managed Service Provider (MSP) industry. After his intense 9-year journey at BrightGauge, Bria…

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The RIF Strategy: How to Turn Facebook Views into Qualified Leads Without Breaking the Bank 38:00

4M ago38:00

38:00

Traditional Facebook advertising is broken. Most businesses waste thousands throwing ads at cold audiences, hoping something sticks. Jamie Gilleland knew there had to be a better way. After building multiple seven-figure companies through marketing automation, Jamie now leads Rift Social - where she's flipped the script on social media marketing. H…

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#135: Vertical SaaS Investor Shares Proven Paths to Scale Up Big – Dave Yuan 55:49

4M ago55:49

55:49

Dave Yuan is the founder of Tidemark, an active growth equity investor focusing on vertical SaaS companies with outsized advantages that can become “control points” in their markets and grow very big. Dave and Tidemark have invested in successful companies like Toast, ServiceTitan, Karbon and Dutchie. In this episode, Dave shares some of the most u…

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What Really Blocks Your Sales Success 42:28

4M ago42:28

42:28

"I got into sales by default, not by intention," admits Steve DeBree. After 30+ years training top sales teams, Steve knows exactly why most people struggle with selling - and it's not about tactics or techniques. In this breakthrough episode, you'll learn: The real reason sales feels uncomfortable (hint: it's deeper than you think) 5 foundational …

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NO CASH, NO PROBLEM: HOW TO HUSTLE YOUR WAY TO THE TOP 1:17:27

4M ago1:17:27

1:17:27

Send us a text What does it really take to go from struggling to thriving? In this raw and motivating episode, e-commerce expert Zoe Khan shares her incredible journey from financial desperation to running a successful agency with over 100 employees. Zoe’s story starts with selling plasma just to afford a phone to apply for jobs. Juggling multiple …

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#134: When It’s Time to Close: Helping Founders Shut Down Right – Dori Yona 44:27

4M ago44:27

44:27

Dori Yona is co-founder and CEO of SimpleClosure, a technology- and people-powered company that helps founders wind down and dissolve a startup or business that is no longer viable. Shutting down a business can be complicated, costly, and risky for founders. SimpleClosure manages the unique processes with automation and expert support. SimpleClosur…

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The Dog Trainer Who Built an Audio Empire One Week at a Time 30:49

4M ago30:49

30:49

After 16 years and over a million downloads, Dr. Robert Forto knows what works in business podcasting - and what doesn't. When skyrocketing yellow pages costs threatened his dog training business in 2009, he turned to podcasting as an alternative marketing channel. This episode reveals the proven strategies behind his longevity and success, includi…

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#133: Bootstrapper Sells School Fundraising Platform to PE Investors - Howard Gottlieb 58:47

5M ago58:47

58:47

Howard Gottlieb started Read-A-Thon in 2012 as a reading-based fundraising platform that helped students raise money while boosting education. Their easy platform and simple fundraising approach created amazing results. The Read-a-Thon business grew steadily and profitably without any outside funding. Read-A-Thon helped over 4000 schools and studen…

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How One Entrepreneur Used Quiz Marketing to Land 6,800 Paying Clients 26:33

5M ago26:33

26:33

Maxwell Nee built a $2 million business in 24 months using an unconventional lead generation approach - quiz marketing. Now serving 6,800 paying clients as CRO of ScoreApp, he shares the exact strategies that doubled and tripled standard conversion rates. Key takeaways from this tactical discussion: - The two psychological threads that make quizzes…

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Foster Care Crisis: 80% of Death Row Inmates & 60% of Traffic Victims — A Call for Reform 55:35

5M ago55:35

55:35

Send us a text Foster care crisis, systemic neglect, shocking statistics, death row, traffic fatalities, urgent reform, social justice. Lisa’s journey is a testament to resilience and the power to create change. After enduring 36 foster homes and facing homelessness at 18, she refuses to let the system’s failures define her future. Now, she’s takin…

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#132: Bootstrapper Serving Private Equity Firms Acquired by PE-Backed Strategic – Richard Change 1:09:35

5M ago1:09:35

1:09:35

Richard Change is co-founder and CEO of PFA Solutions, the provider of FirmView software. FirmView® is the leading carry and compensation management platform for private equity investors to manage their internal compensation from fees and carried interest. Richard was a senior architect for a large private equity firm when he discovered this comple…

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Writing Your Way To Business Authority And Higher Profits 31:00

5M ago31:00

31:00

Nina Hershberger built her first million-dollar direct mail campaign at Notre Dame with zero budget. Now she helps business owners achieve similar results by becoming published authors. In this value-packed episode, Nina reveals how any business owner can leverage the unique authority that comes from having a book. Key takeaways: - Why books work a…