Business is a battle, and we came here to WIN! Carrie and Ian Richardson are partners and serial entrepreneurs who specialize in strategic growth and exit planning for SMBs. Every week, we ask business owners and leaders two important questions: "What's Important Now?" "How are you winning?" Created by entrepreneurs who love strategy, sales and strategic selling, we interview business owners and sales leaders at all stages of growth across multiple industries. Learn from experts sharing thei ...
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Will Ominky and Nerdio's Winning Approach to MSP Events Like Pax 8 Beyond
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18:53Send us a text Carrie Richardson and Ian Richardson host the WIN Podcast - What's Important Now? Serial entrepreneurs, life partners and business partners, they have successfully exited from multiple businesses (IT, call center, real estate, marketing) and they help other business owners create their own versions of success. Ian is certified in Eag…
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MSP Event Planning - How the MSP Initiative Creates Winning MSP Events
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15:34Send us a text Winning MSP Event Planning with Alec Stanners In this episode, we dive deep into what it really takes to plan MSP events that create community, drive real ROI, and elevate vendor relationships beyond the trade show table. Featuring Alec Stanners, VP of Business Development at Bvoip and a core leader behind the MSP Initiative and MSP …
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Aaron Peterik Shares Winning Advice for first-time Sponsors of Pax8 Beyond
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18:47Send us a text From Booths to Buy-In: Aaron Peterik’s Playbook for Winning Pax8 Beyond Episode Description: What separates a vendor with a busy booth from one that builds a sales pipeline? Aaron Peterik, Director of Channel at Zero Networks and former Pax8 insider, joins us to share real-world strategies for dominating Pax8 Beyond. From microsegmen…
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Mark Sokol from CyberFox shares Winning MSP Event Strategies
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17:58Send us a text Carrie Richardson and Ian Richardson host the WIN Podcast - What's Important Now? Serial entrepreneurs, life partners and business partners, they have successfully exited from multiple businesses (IT, call center, real estate, marketing) and they help other business owners create their own versions of success. Ian is certified in Eag…
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Craig Fulton from Evergreen - WIN by Making Lasting Memories
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14:17Send us a text In this episode of The WIN Podcast, host Carrie Richardson interviews Craig Fulton, M&A Advisor at Evergreen Services Group, about how to maximize your experience at industry events like PAX8 Beyond. Craig offers thoughtful advice on preparing for large conferences, engaging meaningfully with other attendees, and creating experiences…
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MSPs WIN When They Collaborate at MSP Industry Events
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10:57Send us a text In this episode of WIN, host Carrie Richardson chats with Allan Jocson, CEO of Agilitec and member of the PAX8 Partner Advisory Council. Allan shares his playbook for getting the most out of major MSP industry events like PAX8 Beyond—from strategic pre-event planning to making meaningful connections that drive long-term growth. You'l…
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Andrew Mora Shares How Cork Wins at MSP Events
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18:49Send us a text Trade shows are back in a big way, and Pax 8 Beyond 2025 is one of the most important events on the MSP calendar. In this episode of the WIN Podcast, host Carrie Richardson talks with Andrew Mora from Cork about what it really takes to turn a sponsorship into a sales strategy. Mora pulls back the curtain on Cork’s full event playbook…
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Winning at Reinvention: Mark Chamberlin on Building Legacy and Active Retirement
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26:34Send us a text From “Who’s Who” to “Who’s He?” – Reinventing Yourself After Leaving Your Business After 40 years in high-tech leadership, Mark Chamberlin found himself at an unexpected crossroads—let go at 61.5 and faced with a big question: What’s next? Instead of chasing another corporate role, he reinvented himself with impact, influence, and fr…
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Winning Customer Transition Strategies for MSPs with Matt Yesbeck
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24:01Send us a text Are you leaving money on the table when offboarding MSP clients? Matt Yesbeck and his son Gage saw a massive gap in the MSP industry—no structured way to transition low-value or misfit clients without losing revenue or damaging reputation. Instead of accepting the status quo, they built MSPX, the first-ever MSP contract exchange plat…
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WIN at Scaling Your MSP with Matthew Pincus and Helpt
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34:25Send us a text Why is Winning at Scale So Difficult? Scaling a business comes with big challenges—hiring, retention, marketing, and making smart decisions that drive growth. In this episode of WIN, host Carrie Richardson sits down with Matthew Pincus, Founder & CEO of HELPT, to discuss the lessons learned from scaling a company, navigating the trad…
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Winning at Social Media Marketing with Heather Margolis
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26:42Send us a text "Winning at Social Media Marketing with Heather Margolis" In this episode of the WIN Podcast, host Carrie Richardson interviews Heather Margolis, founder of Channel Maven, to uncover her strategies for leveraging social media as a powerful tool in B2B marketing. Heather shares invaluable advice on using platforms like Instagram and T…
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Winning Podcast Strategies from Command Your Brand
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29:31Send us a text WIN More PR Opportunities with Advice from Josh Silvestro In this episode, host Carrie Richardson is joined by Josh Silvestro, brand ambassador at Command Your Brand, a podcasting agency specializing in helping businesses amplify their voice and connect with the right audiences. Together, they explore the challenges and opportunities…
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Andrew Moore WINS by Operationalizing Trust
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29:13Send us a text In this episode of What's Important Now, host Carrie Richardson sits down with Andrew Moore, founder of Ridgeview Advisors, to dive deep into the concept of "Operationalizing Trust" in the managed services provider (MSP) industry. Andrew shares insights on how scaling trust is critical for MSPs and how it directly impacts profitabili…
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Mike Ita WINS by supporting one niche specialization.
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28:43Send us a text Host Carrie Richardson sits down with Mike Ita, founder and CEO of IT Corps, a managed service provider based in Ohio. Mike shares his inspiring journey from a general IT consultant to a highly successful niche business specializing in IT services for veterinary practices. He talks about the challenges and triumphs of carving out a u…
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How Waident WINS the best technical talent
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21:03Send us a text Winning Strategies for Recruiting and Retaining Top Talent in the MSP Space In this episode of WIN (What's Important Now), host Carrie Richardson talks with repeat guest John Ahlberg, the CEO of Waident Technology Solutions. They explore Waident's successful strategies for recruiting and retaining talent, especially in the Managed Se…
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Send us a text Daryl D'Souza, Co-Founder of Technique In this episode of the WIN podcast, host Carrie Richardson sits down with Daryl D’Souza, managing partner at Technique, a managed IT services provider based in Toronto, Canada. Daryl shares his unique approach to signing two to three new clients monthly while working only two to three hours a da…
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Justin Breen WINS by Connecting Visionaries to Serve Humanity
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33:46Send us a text In this compelling episode, Carrie Richardson interviews Justin Breen, a master connector who spends his days linking some of the world's most brilliant and misunderstood visionaries. Justin delves deep into the world of high EQ and IQ individuals—those rare few who are focused on creating lasting legacies rather than just building e…
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Kirk Halpern: Restaurants, Redemption Stories, and WINNING
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31:48Send us a text In this episode of "What's Important Now," host Carrie Richardson sits down with Kirk Halpern, the visionary behind Farmers and Fishermen Purveyors. Kirk shares his remarkable journey from practicing law to becoming a major player in the meat and seafood industry. With a passion for supporting small farmers and fishermen, Kirk's late…
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Michelle Accardi WINs by Unlocking Growth
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18:42Send us a text In this engaging episode of the WIN podcast, host Carrie Richardson sits down with Michelle Accardi, the dynamic CEO of LionGard. They discuss Michelle's unique approach to leadership, the importance of working in your flow state, and how LionGard is making strides in the cybersecurity industry. Michelle shares insights into the tran…
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Rob Senatore WINS by surrounding himself with WINNERS.
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20:57Send us a text From Sprint to CEO: Rob Senatore’s Journey with Data2Go Wireless In this episode of the WIN podcast, host Carrie Richardson interviews Rob Senatore, CEO of Data2Go Wireless. Rob shares his inspiring journey from being a sales rep at Sprint to becoming the CEO of a thriving wireless company. He discusses the pivotal moments, challenge…
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Rodrigo Acuna WINS by Helping Hispanic Millennials Build Wealth
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32:53Send us a text Bridging the Financial Gap: Rodrigo Acuna on Empowering Latino Communities In this episode, host Carrie Richardson sits down with Rodrigo Acuna, co-founder of IM Financial, to discuss his journey from Mexico City to the United States, and his passion for empowering Latino communities through financial literacy and inclusion. Rodrigo …
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Joe Alapat Tells Us How Liongard is WINNING with a New CEO
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21:18Send us a text Hi! It's Carrie - and the beginning of this podcast starts really abruptly because Joe and I started chatting immediately and we completely forgot to do the intro. I want to remind MSPs that Liongard ROARCon is open for registration now! Ian and I have limited passes to share, so if it's before July 20 2024 and you are the owner of a…
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Scaling Successfully: WINNING M&A Strategies for MSPs
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35:45Send us a text Christopher Vollmond-Carstens, M&A, NTIVA In this episode of WIN ("What's Important Now?"), host Carrie Richardson dives into the world of mergers and acquisitions (M&As) within the managed service provider (MSP) industry with Christopher Vollmond-Carstens, M&A Director at NTIVA. Christopher shares invaluable insights on preparing MS…
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David Dulany Helps SaaS teams WIN by choosing the right Sales Technology Stack
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31:24Send us a text David Dulany, Founder of Tenbound In this episode of the WIN podcast, host Carrie Richardson sits down with David Dulany, the founder of Tenbound, a premier research and advisory firm in the B2B tech space. They discuss the journey of Tenbound, the evolution of sales technology, and the intricacies of building a successful sales deve…
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Pedro Lerma WINS by building brands while breaking barriers
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23:25Send us a text Pedro Lerma - EY Entrepreneur of the Year Nominee 2024 In this episode of "WIN: What's Important Now," host Carrie Richardson sits down with Pedro Lerma, the founder of Lerma, an innovative advertising agency based in Dallas. Pedro shares his entrepreneurial journey, from his early experiences in construction and bar ownership to cre…
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Carlson Choi WINs with a focus on partnerships instead of transactions
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28:37Send us a text In this episode of WIN, host Carrie Richardson sits down with Carson Choi, CEO of Cork, to discuss his dynamic career path from enterprise leadership to founding Cork, a company that revolutionizes cyber insurance with a unique cyber warranty product. Carson shares his insights on the MSP space, the challenges of cyber risk managemen…
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Dave Marcinkowski WINS by Innovating in a Tech-Adverse Industry
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28:12Send us a text Episode Summary In this episode of Win What's Important Now, host Carrie Richardson interviews Dave Marcinkowski, founder of Madera Residential and nominee for the EY Entrepreneur of the Year award. Dave shares his entrepreneurial journey from his early days as a bookkeeper to leading multiple successful ventures in real estate, prop…
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Shaun Vlassis WINS by Innovating Threat Detection
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27:54Send us a text Shaun Vlassis Wins By Innovating Threat Detection In this episode of "What's Important Now?" host Carrie Richardson sits down with Shaun Vlassis, founder of Illuminate Security, to explore the creation and impact of his innovative crowdsourced threat hunting platform, Blue Hat. Shaun shares his journey from working at top financial i…
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Josh Kotler wants other MSPs to WIN by Selling Before the Bubble Bursts
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26:10Send us a text In today's episode of "What's Important Now," we had the pleasure of speaking with Josh Kotler, a seasoned investor in the managed services space and a partner at Axial Reade. Josh shared his journey from founding Western Digitech to his recent ventures, providing valuable insights into the MSP industry and the M&A process. Josh's st…
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Sanjay Jupudi bootstraps Qentelli to a 9 figure valuation - EoY Series 2024
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21:28Send us a text Welcome to today’s episode of the WIN podcast with Carrie Richardson. Today we kick off our annual "EY EoY Interview Series" with 2024 EY Entrepreneur of the Year Nominee Sanjay Jupudi, co-founder and CEO of Qentelli. Qentelli (Kwen–Tel–LEE) is a Digital and Cloud Technology Company. Their Intellectual Property includes AI based prod…
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John Ahlberg WINs By Using a Defined M&A Process
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27:46Send us a text John Ahlberg, the founder and CEO of Waident Technology Solutions, recently joined Carrie Richardson on the podcast WIN - What's Important Now? to discuss his company's growth through mergers and acquisitions (M&A). Celebrating its 20th anniversary, Waident has about 30 employees and over $7 million in annual recurring revenue, makin…
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Matt Quammen WINS by Protecting Small Business Owners
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24:06Send us a text Matt Quammen is the co-founder of Optimize Cyber, a company that specializes in cybersecurity services such as penetration testing and risk assessments. With a background in technology and sales, Matt brings a wealth of experience to the table, particularly in the realm of cybersecurity. His approach to the field is not just about th…
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Nate Freedman Helps MSPs Build Websites that WIN more clients!
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19:56Send us a text Nate Freedman Helps MSP Clients WIN more Clients Join Carrie Richardson, host of WIN as she chats with Nate Freedman, the CEO of Tech Pro Marketing. Unlock the secrets of transforming casual website browsers into committed clients with live chat. That's just a slice of what we're serving up as we sit down with the CEO of TechPro Mark…
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Send us a text Paul Schmidt uses Networking to WIN! When the world seemed to crumble on September 11, 2001, Paul Schmidt embarked on a venture that would prove his resilience in the face of adversity. Tune in to hear how Paul's Uno Deuce Multimedia carved a niche in Lansing's entrepreneurial landscape, transforming crisis into opportunity with adap…
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Jim Doyle WINS by Selling With A Servant Heart
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34:10Send us a text When the quest for success in sales becomes more than just numbers and contracts, it transforms into an art form. That's the philosophy Jim Doyle, author of "Selling with a Servant Heart" and founder of JDA Media, brings to the table in our latest episode. From the early days of selling candy as a young Boy Scout to his rise as a med…
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Send us a text Jim Smith from Proper Sky IT WINS by Keeping Clients Secure In this episode of WIN, host Carrie Richardson sits down with Jim Smith, the founder and CEO of Proper Sky, a managed service provider based in Philadelphia. Episode Highlights Jim's Early Entrepreneurial Ventures: Studying entrepreneurial studies at Drexel University and st…
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Scott Daigger helps Entrepreneurs WIN their battles with Online Marketing.
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26:30Send us a text Scott Daigger, the strategic brain behind Buddy Web Design and Development, joins me, Carrie Richardson, on WIN for an inspiring recount of his journey into entrepreneurship. Scott peels back the layers of his career transformation, revealing how a blend of coding curiosity and a robust business acumen propelled him from the healthca…
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Michael Nelson WINS by Scaling Remote Teams
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29:43Send us a text Michael Nelson WINs by Scaling Remote Teams Embark on a captivating journey with Michael Nelson, a former middle school teacher turned tech entrepreneur, as he recounts the pivotal moments of founding Scaled. From humble beginnings teaching in inner-city schools, to creating websites to facing the tumultuous dot-com bubble, Michael's…
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David De Camillis WINS with Strategic Mergers and Marketing Innovation in Managed Services
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25:26Send us a text Mergers & Marketing With David DeCamillis Embark on an expedition through the intricate landscape of merging managed service providers, as Carrie Richardson teams up with the savvy David De Camillis to talk marketing and mergers. Uncover the secrets to navigating blending disparate business cultures, processes, and technologies, all …
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Ryan Grimes Keeps WINNING - A One Year Check In
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19:32Send us a text Join the conversation with the ever-insightful Ryan Grimes, founder of My IT Indy, as we revist his IT business one year after our last podcast with him! With a narrative that's bound to resonate with entrepreneurs and tech aficionados alike, Ryan shares the tactical sales and marketing maneuvers that accelerated My IT Indy from its …
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Dustin Bolander WINs By Simplifying Cybersecurity Insurance for SMBs
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33:20Send us a text Join me as I sit down with Dustin Bolander, a visionary entrepreneur who has carved a path from leading a Managed Service Provider to pioneering a cybersecurity insurance firm. In a gripping recount of his professional voyage, Dustin outines his transition from IT to the intricacies of the insurance world. Our dialogue journeys throu…
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WIN with Debbie Kestin by Unlocking the Vault of Vendor Marketing Funds
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25:01Send us a text Join me: Carrie Richardson, partner at Richardson & Richardson Consulting, on today's episode of WIN, where we talk about something everyone likes: free money! Unlock the mysteries of Market Development Funds and Joint Marketing Funds with the expertise of Debbie Kestin, the marketing guru from Kestin Impact Consulting. You're in for…
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Ian Richardson Fox & Crow Perspective Before Planning In Marketing
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17:39Send us a text Have you ever wondered why some marketing plans lead to a cascade of new clients while others fizzle out? Join me, Carrie Richardson, and my expert co-host, Ian Richardson, as we pull back the curtain on constructing a marketing strategy that hits the mark every time. We take you through the trenches of our own marketing journey with…
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Bart Justice WINS by Mastering Decision-Making with the Judgment Index and Aligning Core Values
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20:48Send us a text Discover the keys to unlocking stellar decision-making in the corporate world with me, Carrie Richardson, as I sit down with Bart Justice, an innovator at the helm of Arise Forums. Prepare to have your mind broadened as we traverse the landscape of the Judgment Index, an assessment tool that transcends your typical personality quizze…
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Michael Cervino WINS by Navigating the Seas of Pandemic and AI in Managed Services
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26:02Send us a text Join Carrie Richardson, Partner at Richardson & Richardson Consulting and Founder of Croocial as she asks entrepreneurs an important question, "What's Important Now?" Starting with his founders journey, and ending with his latest WIN, this week's guest is Michael Cervino from Circle Square Consulting in Pennsylvania. Michael has buil…
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Angela Chryplewicz WINS by Merging Family, Creativity, and Business
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28:46Send us a text Carrie Richardson, partner at Richardson & Richardson Consulting and founder of the content collaboration company, Croocial, hosts today's episode of WIN! Angela Chryplewicz, the co-owner of Lasting Impressions in Canton Michigan is the second entrepreneur from this business to appear on WIN! Listen to Carla Ejaz's WIN recording abou…
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James Riley WINS by Balancing Entrepreneurship and a Successful Marriage
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23:13Send us a text What if we told you that being an engineer and running a successful business is not only possible but can also be enjoyable? Carrie Richardson, Partner at Richardson & Richardson Consulting, is your host for this episode of What's Important Now. Meet James Riley, a remarkable engineer-turned-entrepreneur, who has grown a small IT ser…
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Harrison Leffel-Jones WINS by Supporting Entrepreneurs
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15:36Send us a text Join Carrie Richardson and her guest, Harrison Leffel-Jones, Executive Director of the Lansing Regional SmartZone. In this episode of WIN, Harrison shares an overview of how the Lansing Smart Zone assists new and existing entrepreneurs. Learn how you can connect with other experts, mentors and start-up enthusiasts in mid-Michigan. Ca…
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The Pumpkin Plan Helps Dave Cava's TSP Clients WIN!
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25:31Send us a text Dave Cava grew his MSP to an impressive 10MM in annual revenue prior to his exit in 2017. Post-exit, he joined Shawn Walsh as a partner in Encore Strategic, a consulting and strategic planning group. When he first joined Encore, Dave was primarily responsible for recruiting talent for their growing MSP clients. Shawn and Dave have co…
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Embracing Remote Workforces Helps Jamison West WIN!
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23:38Send us a text Jamison West is a serial entrepreneur who has founded, and scaled multiple technology, services, and software as a service companies, including Arterian, SmileBack, TimeZest, ConnectStrat and now, in partnership with Doxa, MSP Talent. Jamison, unlike many founders in the MSP space, started his entrepreneur career with a business educ…
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