Audacity of Entrepreneurs

audacityofentrepreneurs

Audacity of Entrepreneurs is a podcast about what it actually takes to build something from scratch, and survive the process. Every episode dives deep into the journeys of founders, operators, and creators who chose to take risks when playing safe was easier. We go beyond highlight reels and vanity metrics to unpack the real mechanics behind building companies: the messy beginnings, the wrong bets, the pivots, and the breakthroughs that changed everything. This podcast focuses on: Decision-making under uncertainty - how founders think when there’s no clear path Execution over ideas - what separates builders from talkers Failure analysis - what went wrong, and what it taught them Growth systems - content, distribution, hiring, and scaling strategies Founder psychology - discipline, obsession, burnout, and resilience You’ll hear unfiltered conversations about: First customers and early traction Scaling from 0 to meaningful revenue Building teams, culture, and systems Navigating competition, doubt, and pressure The trade-offs no one warns you about If you’re an entrepreneur, creator, or operator trying to build something meaningful, this podcast gives you real-world insight, not recycled advice. No clichés. No surface-level motivation. Just honest conversations with people who’ve done the work.

  1. 2d ago

    SMB Acquisition Playbook: Upfront Cash, Earnouts, and Rollover Equity | Joshua Soloway | EP 118

    What if growing your business does not mean building everything from scratch, but finding the right company to acquire, structuring the deal carefully, and managing what happens after the acquisition? In this insightful episode of Audacity of Entrepreneurs, Nick Uresin sits down with Joshua Soloway, Managing Director of Soloway Group PC, for a practical conversation about growing small and midsize businesses through acquisitions, choosing the right acquisition targets, structuring deals, and managing change after a business is acquired. Joshua brings experience from building and selling a law firm, scaling several other businesses, and building the New York office of a global management consulting firm. He also discusses his recent acquisition of Willinger, Willinger & Bucci, a full-service regional law firm. At the center of the conversation are three important parts of an acquisition: choosing a business that fits your growth strategy, creating a deal structure that works for both sides, and preparing for the cultural and operational changes that follow. Joshua explains why buyers should look for businesses that can strengthen what they already do. That could mean acquiring a competitor, expanding into a new geographic market, adding a related service, or finding a business that serves clients who may also need your existing services. The goal is not simply to buy another company. It is to find an acquisition where the combined businesses can create more value together than they could separately. In this episode, you'll discover: How to determine whether a company is the right acquisition target Why complementary businesses can create greater value together How acquisitions can help companies enter new markets or add services Why different customer acquisition models are not always a deal breaker When acquiring an outside service provider may or may not make sense Why building your own technology is different from becoming a technology company How upfront cash, earn-outs, and rollover equity can shape an acquisition Why sellers may choose between more cash today and more long-term upside How working capital and business performance can affect deal terms Why buyers and sellers should consider both overperformance and underperformance Why change management should be considered before an acquisition closes How long-standing company cultures can create resistance to change Why finding internal champions can make post-acquisition changes easier How better operations, marketing, and financial controls can create new growth opportunities Download your complimentary Legal Health Check Guide by The Soloway Group Identify and address potential legal risks with a a clear framework for organizing key documents and uncovering vulnerabilities, empowering you to safeguard your operations and prepare for future opportunities. Here is the download link: https://www.solowaygroup.com/free-resource/ Joshua also explains why acquisition strategy should begin with understanding what type of buyer you are. A company expanding an existing business has different goals from an investor looking for a lower-maintenance business. For growth-focused entrepreneurs, the key question is whether the target can add meaningful value to the core company. The conversation also explores deal structure in detail. Joshua discusses three common components in professional services acquisitions: upfront cash, earn-outs, and rollover equity. He explains how these tools can balance risk, reward sellers for future performance, and keep key people invested in the long-term success of the combined business. The final part of the conversation focuses on what happens after the deal closes. Joshua explains why change management can be difficult, especially in businesses where employees have worked together for many years. New management systems, marketing investments, financial controls, and operating processes can create opportunities, but they can also create resistance. One important step is identifying the people inside the acquired company who believe in the new direction. Joshua explains that these internal champions are not always the most senior or highest-paid people. They may be employees who have been waiting for the opportunity to contribute ideas, improve systems, and move the company forward. His message is clear: a successful acquisition is about more than buying a business. You need the right strategic fit, a thoughtful deal structure, and a plan for bringing people and operations together after the deal closes. If you're an entrepreneur, business owner, or leader considering acquisitions as a path to growth, this conversation offers a practical look at what to evaluate before making a deal and what to prepare for once the acquisition is complete. 🎙️ Listen to the full episode to learn how to evaluate acquisition targets, structure a deal, manage post-acquisition change, and use acquisitions to build a stronger business. About Audacity of Entrepreneurs Hosted by Nick Uresin, Audacity of Entrepreneurs features conversations with founders, CEOs, and business leaders sharing practical insights on entrepreneurship, leadership, sales, and business growth. 👍 Subscribe for more actionable business and sales insights. #Entrepreneurship #BusinessGrowth #Acquisitions #MergersAndAcquisitions #BusinessStrategy #DealStructure #ChangeManagement #Leadership #SMB #AudacityOfEntrepreneurs

    SMB Acquisition Playbook: Upfront Cash, Earnouts, and Rollover Equity | Joshua Soloway | EP 118
  2. Oct 26

    The Show Was the Marketing: The Acquisition Was the Accident | Tom Truitt | EP 117

    What does it take to launch a business in an industry where you have no experience, no contacts, and no credibility, right as that industry is falling apart? In this episode of Audacity of Entrepreneurs, Nick Uresin sits down with Tom Truitt, founder of Music Row Search, to explore how a management consulting headhunter became the go-to executive recruiter for the music industry. Tom spent the first 13 years of his career recruiting for the world's largest consulting firms during the first internet boom, eventually managing about 75 people. But after the tech bubble burst and 9/11, he realized he wasn't having fun anymore. He sold his interest, waited out a non-compete, and spent five years selling Cranium, then the hottest board game on earth. In 2007, he came home from a long trip and told his wife he was getting into the music business. While meeting senior executives on Music Row in Nashville, he kept asking one question: who are the go-to headhunters in this industry? The answer was always the same. Nobody. So he became one. Tom launched Music Row Search in the spring of 2007, just as digital disruption was tearing through the record business and a year before the financial crisis. His first search came through a single phone call and landed him Beyoncé's management company as a client. Now, nearly 20 years later, Tom shares how he survived the 2008 recession, launched a video job-pitch startup, joined a company that was acquired by AOL, relaunched his search firm, and built a platform that keeps bringing him business. In this episode, you'll discover: Why Tom walked away from a successful headhunting career at 40 How asking one simple question revealed a gap in the music industry How he landed Beyoncé's management company as his first client Why every early search he landed had "digital" in the title The challenge of building a business that serves two audiences Why the client comes first in executive search Why Tom proudly calls himself a headhunter How the 2008 recession nearly sank his business How a Christmas video shoot in August inspired a new startup How Your Elevator Pitch helped job seekers stand out with video How a venture capital rejection led to a role at Studio Now and an AOL acquisition Why he kept Music Row Search alive on the back burner How the Zulu Principle explains the power of a narrow niche How live events and a 300-episode webinar series became his marketing engine How a Variety feature led to joining Turnkey's sports search practice Why selling books door to door gave him thick skin and a short memory If you're an entrepreneur, executive recruiter, career changer, or founder thinking about entering an industry from the outside, this conversation is packed with practical lessons about spotting gaps, building relationships, surviving downturns, and owning a niche. Subscribe to Audacity of Entrepreneurs for more unfiltered conversations with founders, executives, and business leaders about the decisions, challenges, and strategies behind building remarkable companies. 👍 Subscribe for more actionable leadership and remote work insights. About Audacity of Entrepreneurs Hosted by Nick Uresin, Audacity of Entrepreneurs features conversations with founders, CEOs, and business leaders sharing practical insights on entrepreneurship, leadership, sales, and business growth. #Entrepreneurship #ExecutiveSearch #MusicIndustry #Headhunter #Recruiting #MusicBusiness #NicheBusiness #Entrepreneur #BusinessGrowth #AudacityOfEntrepreneurs

    The Show Was the Marketing: The Acquisition Was the Accident | Tom Truitt | EP 117
  3. Oct 19

    The Only Forward-Looking Metric in Business: Share of Voice Explained | Tara Coomans | EP 116

    What happens when you want out of a business you built with a partner, and nobody planned for that moment? In this episode of Audacity of Entrepreneurs, Nick Uresin sits down with Tara Coomans, CEO and founder of Avaans Media PR, to explore what she learned from selling her shares to business partners twice, and the forward-looking metric most companies ignore. Tara started her first business in event marketing at 24 and sold it to her partner four years later. She then took a job at a trade magazine, and within a short time she and two colleagues bought the magazine and a trade show. They added more publications and events before she exited again, this time through a buyout that took years and required a lawyer for her to get paid. Those two exits taught her the lesson she now puts first: plan for someone to leave before you ever open the doors. That means talking through valuation, buyout terms, and shareholder rights while everyone still agrees. Today, Tara runs a PR agency that helps growth-stage companies in regulated industries secure earned media. She shares why share of voice compared to market share is one of the few metrics that tells you where your business is heading, not just where it has been. In this episode, you'll discover: Why you should plan your exit when you write your business plan How selling to a partner differs from selling to a third party or private equity firm Why emotions and sweat equity complicate partner buyouts How a shareholders agreement can spell out buyout rights and valuation in advance How to record sweat equity so it can be converted later Why going into business with friends, family, or a spouse is a risky move What happens when a partner's spouse suddenly gains influence in the business How Tara knew it was time to leave each of her businesses What share of voice is and how to measure it Why share of voice greater than market share signals growth, and less signals decline How share of voice strengthens your position in acquisition, IPO, and investment conversations Why impressions and media hit counts matter less than how people perceive your company How podcasts, earned media, contributed articles, and your own content build share of voice Why "all news is good news" is a risky belief, especially in the age of AI How smaller businesses can track share of voice without expensive platforms How growing up with an entrepreneurial father shaped Tara's path If you're an entrepreneur, business owner, co-founder, or growth-stage leader, this conversation is packed with practical lessons about partnerships, exit planning, company valuation, and building the visibility that drives future growth. Subscribe to Audacity of Entrepreneurs for more unfiltered conversations with founders, executives, and business leaders about the decisions, challenges, and strategies behind building remarkable companies. About Audacity of Entrepreneurs: Hosted by Nick Uresin, Audacity of Entrepreneurs features conversations with founders, CEOs, and business leaders sharing practical insights on entrepreneurship, leadership, sales, and business growth. 👍 Subscribe for more actionable business and sales insights. #Entrepreneurship #BusinessPartnership #ExitStrategy #ShareOfVoice #PublicRelations #BusinessGrowth #Entrepreneur #EarnedMedia #BusinessValuation #AudacityOfEntrepreneurs

    The Only Forward-Looking Metric in Business: Share of Voice Explained | Tara Coomans | EP 116
  4. Oct 12

    Why Short Ads Fail in Business: Inside the Branded Documentary Model | William Kruse | EP 115

    How do you turn corporate messaging into authentic human connection, build trust with high-stakes audiences, and elevate your brand through cinematic storytelling? In this episode of Audacity of Entrepreneurs, Nick Uresin sits down with William Kruse, founder and creative director of Clever. William shares his perspective on documentary filmmaking, motion content strategy, long-form branded storytelling, and the irreplaceable value of human connection in an increasingly AI-driven market. Together, they explore how business leaders can bridge the gap between entertainment-quality media and commercial marketing to build long-term authority and customer loyalty. William Kruse is a former filmmaker with nearly two decades of experience in independent cinema, production, and creative direction. Through Clever, he helps healthcare and medtech brands create series-based short documentaries that connect deeply with patients and physicians alike. Combining a background in film theory from Notre Dame and industry production from Florida State, William brings a rare mix of artistic vision, strategic messaging, and execution discipline to modern brand strategy. William explains that true audience engagement comes down to authentic human stories rather than pitch-heavy commercial spots. He breaks down how dropping into cities to shoot broadcast-quality series in 48 hours creates high-value brand assets, why longer runtimes serve information-hungry audiences in regulated spaces, and how documentary archetypes allow viewers to see themselves in your message. He also takes a passionate stand on the front lines of the creative response to AI, advocating for genuine human empathy in visual media. In this episode, you'll discover: Why standard corporate video fails and how documentary principles fill the gap How to bridge the divide between commercial marketing and independent filmmaking The power of series-based content for sustained audience engagement and touchpoints Why high-stakes industries (like healthcare) require longer-form, information-rich storytelling How high-end broadcast production values instantly elevate brand authority The mechanics of motion content strategy, production, and activation Why conducting deep audience research before writing a script guarantees high engagement How executing 48-hour sight-unseen shoots builds high-impact content on tight schedules Why human intelligence and authentic connection will outlast automated creative AI How documenting real human experiences leaves a lasting business and visual legacy If you're an entrepreneur, marketing executive, agency leader, or brand strategist, this conversation is packed with practical lessons about choosing the right content format, overcoming market friction, engaging complex audiences, and building a brand that stands out. Subscribe to Audacity of Entrepreneurs for more unfiltered conversations with founders, executives, and business leaders about the decisions, challenges, and strategies behind building remarkable companies. Whether you're launching your first startup or leading an established company, this conversation is packed with practical strategies you can implement immediately. 👍 If you enjoyed this episode, Like, Subscribe, and turn on notifications for more conversations with founders, executives, and entrepreneurs building remarkable businesses. #Entrepreneurship #Leadership #BusinessGrowth #ScalingBusiness #EOS #BusinessSystems #KPIs #Amazon #Startup #CompanyCulture

    Why Short Ads Fail in Business: Inside the Branded Documentary Model | William  Kruse | EP 115
  5. Oct 5

    From Authority to Legacy: How Founders Build Trust That Outlives Them | Greg Mischio | EP 114

    How do you turn your expertise into authority, authority into trust, and your personal story into a lasting business legacy? In this episode of Audacity of Entrepreneurs, Nick Uresin sits down with Greg Mischio, founder of Winbound Digital Marketing Agency. Greg shares his perspective on content, thought leadership, authority, and relationship-building. Together, they explore how entrepreneurs can turn expertise and storytelling into meaningful business opportunities. Greg Mischio is a writer, entrepreneur, and digital marketing strategist with a strong focus on content and thought leadership. Through Winbound, he helps businesses use expertise, research, storytelling, and strategic distribution to establish authority. He also brings a deep passion for writing, including books and memoirs that preserve people's experiences and ideas. Greg explains that true authority ultimately comes down to trust. He shares how personal experience, original research, and credible third-party experts can strengthen thought leadership. He also discusses why business leaders should be visible in their company's content and how podcasts can create powerful relationships beyond traditional marketing. Greg explains how conversations, podcasts, books, and personal stories can deepen relationships and preserve valuable experiences. For him, legacy is ultimately measured by the impact you make, not simply by the success you achieve. In this episode, you'll discover: Why authority is ultimately built on trust How personal experience and storytelling strengthen credibility The role of research and third-party expertise in thought leadership Why executives should be visible in their company's content How to balance content creation with effective distribution Why podcasts can become powerful relationship-building tools How content can create business-development opportunities Why your personal story may be more valuable than you realize How documenting your experiences can contribute to your legacy Why lasting impact matters beyond financial success If you're an entrepreneur, agency owner, business leader, or aspiring founder, this conversation is packed with practical lessons about making the leap, finding your competitive advantage, acquiring customers, and building a business that lasts. Subscribe to Audacity of Entrepreneurs for more unfiltered conversations with founders, executives, and business leaders about the decisions, challenges, and strategies behind building remarkable companies. About Audacity of Entrepreneurs Hosted by Nick Uresin, Audacity of Entrepreneurs features conversations with founders, CEOs, and business leaders sharing practical insights on entrepreneurship, leadership, sales, and business growth. #Entrepreneurship #Marketing #BusinessGrowth #AgencyOwner #Entrepreneur #DigitalMarketing #PersonalBrand #PodcastMarketing #AI #AudacityOfEntrepreneurs

    From Authority to Legacy: How Founders Build Trust That Outlives Them | Greg Mischio | EP 114
  6. Sep 28

    Customer Advocacy: How to Make Clients Your Best Salespeople | Stephen Dean | EP - 113

    What if your customers could become one of the strongest forces helping you grow your business? In this insightful episode of Audacity of Entrepreneurs, Nick Uresin sits down with Stephen Dean, COO & Co-founder of Keona Health, for a practical conversation about customer relationships, healthcare call centers, referrals, product development, resilience, and turning customers into advocates. Stephen shares how Keona Health works with healthcare call centers using a healthcare CRM designed to improve patient service, simplify complex workflows, and help organizations operate more effectively. He explains why healthcare call centers can be incredibly difficult to manage, with some workflows involving millions of possible paths and agents often needing months of training before they can work independently. But the conversation goes much deeper. Stephen explains how Keona Health builds close customer relationships through regular operational meetings, executive reviews, data analysis, focus groups, and customer communities. By listening carefully, measuring what customers may take for granted, and helping them solve real problems, the company creates relationships based on mutual investment. In this episode, you'll discover: Why strong customer relationships can become a powerful growth engine How regular operational meetings help uncover customer pain points Why executive conversations should focus on business results and strategic goals How Keona Health measures complex healthcare call center workflows Why comparing performance over time can reveal meaningful improvements How customer data can become useful marketing content Why warm referrals can be more effective than cold outreach How case studies can turn satisfied customers into advocates Why listening to customers can lead to valuable product ideas How customer feedback helped shape Keona Health's healthcare CRM Why measuring a problem matters before trying to solve it How collaboration can make customers feel invested in a product Why mutual investment is at the center of strong customer relationships How Stephen's early life on a farm helped shape his resilience Why entrepreneurs need to keep investing in others during difficult times Stephen also opens up about growing up on a farm, moving frequently after his father began working for a military contractor, living in 14 states, working inside early-stage startups, and eventually discovering that entrepreneurship gave him something traditional employment could not. He also shares how Keona Health's first product evolved after a customer encouraged the company to expand beyond its original focus. That customer feedback helped shape the broader healthcare CRM Keona Health provides today. His message is simple but powerful: measure what your customers take for granted, help them improve it, and they can become some of your strongest advocates. If you're an entrepreneur, SaaS founder, executive, or business leader looking to improve customer retention, generate referrals, develop better products, or build deeper customer relationships, this conversation offers practical lessons you can apply. 🎙️ Listen to the full episode and discover how stronger customer relationships can help you improve your product, create advocates, and grow your business. #Entrepreneurship #CustomerSuccess #SaaS #HealthcareTechnology #CustomerExperience #BusinessGrowth #Leadership #ProductDevelopment #CustomerRetention #AudacityOfEntrepreneurs

    Customer Advocacy: How to Make Clients Your Best Salespeople | Stephen Dean | EP - 113
  7. Sep 14

    Play for a Living: Why Serious Companies Are Getting Playful | Meredith Martini | EP - 112

    What if one of the best ways to build stronger teams is simply to play more? In this episode of Audacity of Entrepreneurs, we sit down with Meredith Martini, CEO of PlayWorks Group LLC, to explore how play can help build trust, psychological safety, stronger relationships, and more engaged teams. Learn why play is more than just having fun, how leaders can bring playful thinking into everyday work, and why team building works best when it becomes part of company culture. You'll also hear practical ideas for icebreakers, playful communication, remote team activities, and handling workplace tension in healthier ways. Meredith shares why leaders should start small, respect employee boundaries, make play part of the regular work rhythm, and create environments where people feel comfortable connecting, contributing, and speaking up. In this episode, you'll learn: Why play can help build trust and psychological safety at work How leaders can introduce play without making employees uncomfortable Simple icebreakers that help teams connect and communicate How curiosity, humor, and storytelling can create a more playful culture Why employees should have the choice to participate at their comfort level How remote and global teams can use play to build stronger connections Why team building should happen during work hours whenever possible How regular play can strengthen trust, engagement, and team relationships Why play can support learning, creativity, innovation, and performance The business cost of low engagement, poor retention, and employee turnover Meredith also shares how her childhood, family experiences, work with young people, and study of counseling helped shape her understanding of the power of play and eventually influenced the work she does today. Whether you lead an in-person, hybrid, or fully remote team, this conversation offers practical ways to make play part of your workplace culture while building stronger relationships and more connected teams. 👍 If you enjoyed this episode, Like, Subscribe, and turn on notifications for more conversations with founders, executives, and entrepreneurs building remarkable businesses. #Entrepreneurship #Leadership #TeamBuilding #CompanyCulture #EmployeeEngagement #WorkplaceCulture #PsychologicalSafety #RemoteTeams #PlayAtWork #BusinessGrowth

    Play for a Living: Why Serious Companies Are Getting Playful | Meredith Martini | EP - 112
  8. Sep 7

    Using The Unstuck Audit To Create A 5-Year Plan | Melanie Asher | EP - 111

    What if getting unstuck in business starts with understanding what you can control, measuring what truly matters, and building a clear plan for the future? In this insightful episode of Audacity of Entrepreneurs, Nick Uresin sits down with Melanie Asher, MBA, CEPA, Adjunct Professor at Saint Martin’s University, Co-Founder & CEO at Validera, and Founder & Fractional Executive at Omicle, for a practical conversation about business growth, valuation, changing markets, customer acquisition, and long-term planning. Melanie shares how businesses can respond when revenue is inconsistent, growth has stalled, or market conditions are changing. Instead of focusing on outside forces that cannot be controlled, she explains why founders should examine their strategy, systems, policies, technology, metrics, and other areas they can directly improve. At the center of the conversation is Melanie's Unstuck Audit, a methodology that examines nine key areas of a business, including vision and strategy alignment, brand positioning, go-to-market and revenue maturity, founder dependency and leadership, operational maturity, financial performance, risk, compliance and IP, growth and expansion readiness, and transition, exit and personal readiness. The goal is not to predict exactly what will happen five years from now. It is to build a stronger and more valuable business that is prepared to adapt when conditions change. In this episode, you'll discover: How the Unstuck Audit helps businesses identify where they are stuck Why founders should focus first on what they can control How to turn a long-term business vision into an actionable plan Why a 5-year plan should prepare a company for change, not try to predict the future The nine business areas examined through the Unstuck Audit How business readiness and market attractiveness affect business value Why founder dependency can become a major barrier to scaling How leadership alignment can influence business growth Why likes, comments, and shares may not be the metrics that matter most How the right metrics can connect business activity to meaningful goals Why licensing or franchising can sometimes create new paths for growth How AI is changing marketing, testing, advertising, and customer acquisition Why personal referrals continue to create strong trust in B2B sales Why podcasting can require patience before producing meaningful business results Melanie also shares her own path into entrepreneurship. She explains how curiosity shaped her journey, from asking questions in school and college to discovering entrepreneurship through hands-on projects. That same curiosity continues to influence how she approaches business problems today. The conversation also explores how companies such as Amazon and Netflix adapted their strategies as markets and technology changed, and why businesses need the ability to adjust instead of simply chasing what happened last week. Her message is clear: you cannot predict every change, but you can build a business that is better prepared for what comes next. If you're an entrepreneur, founder, or business leader dealing with inconsistent revenue, stalled growth, changing market conditions, or long-term planning, this conversation offers a practical way to understand where your business stands and what to improve next. 🎙️ Listen to the full episode to discover how the Unstuck Audit can help you create a 5-year plan, strengthen your business, increase its value, and prepare for growth. #Entrepreneurship #BusinessGrowth #BusinessStrategy #Leadership #UnstuckAudit #BusinessValuation #StrategicPlanning #B2BMarketing #FounderLeadership #AudacityOfEntrepreneurs

    Using The Unstuck Audit To Create A 5-Year Plan | Melanie Asher | EP - 111

Ratings & Reviews

5
out of 5
2 Ratings

About

Audacity of Entrepreneurs is a podcast about what it actually takes to build something from scratch, and survive the process. Every episode dives deep into the journeys of founders, operators, and creators who chose to take risks when playing safe was easier. We go beyond highlight reels and vanity metrics to unpack the real mechanics behind building companies: the messy beginnings, the wrong bets, the pivots, and the breakthroughs that changed everything. This podcast focuses on: Decision-making under uncertainty - how founders think when there’s no clear path Execution over ideas - what separates builders from talkers Failure analysis - what went wrong, and what it taught them Growth systems - content, distribution, hiring, and scaling strategies Founder psychology - discipline, obsession, burnout, and resilience You’ll hear unfiltered conversations about: First customers and early traction Scaling from 0 to meaningful revenue Building teams, culture, and systems Navigating competition, doubt, and pressure The trade-offs no one warns you about If you’re an entrepreneur, creator, or operator trying to build something meaningful, this podcast gives you real-world insight, not recycled advice. No clichés. No surface-level motivation. Just honest conversations with people who’ve done the work.