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 two important questions: "What's Important Now?" "How are you winning?" Created by entrepreneurs and featuring entrepreneurs, we interview business owners at all stages of growth across multiple industries. Learn from experts sharing their strategies and the tactics they use to identify ...
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Justin Breen WINS by Connecting Visionaries to Serve Humanity
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Send us a Text Message. 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 b…
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Kirk Halpern: Restaurants, Redemption Stories, and WINNING
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Send us a Text Message. 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, Ki…
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Michelle Accardi WINs by Unlocking Growth
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Send us a Text Message. 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…
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Rob Senatore WINS by surrounding himself with WINNERS.
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Send us a Text Message. 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, …
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Rodrigo Acuna WINS by Helping Hispanic Millennials Build Wealth
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Send us a Text Message. 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.…
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Joe Alapat Tells Us How Liongard is WINNING with a New CEO
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Send us a Text Message. 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 o…
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Scaling Successfully: WINNING M&A Strategies for MSPs
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Send us a Text Message. 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 pre…
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David Dulany Helps SaaS teams WIN by choosing the right Sales Technology Stack
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Send us a Text Message. 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 s…
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Pedro Lerma WINS by building brands while breaking barriers
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Send us a Text Message. 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 ownersh…
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Carlson Choi WINs with a focus on partnerships instead of transactions
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Send us a Text Message. 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 …
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Dave Marcinkowski WINS by Innovating in a Tech-Adverse Industry
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Send us a Text Message. 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 est…
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Shaun Vlassis WINS by Innovating Threat Detection
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Send us a Text Message. 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 fi…
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Josh Kotler wants other MSPs to WIN by Selling Before the Bubble Bursts
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Send us a Text Message. 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. …
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Sanjay Jupudi bootstraps Qentelli to a 9 figure valuation - EoY Series 2024
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Send us a Text Message. 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 b…
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John Ahlberg WINs By Using a Defined M&A Process
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Send us a Text Message. 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 reven…
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Matt Quammen WINS by Protecting Small Business Owners
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Send us a Text Message. 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…
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Nate Freedman Helps MSPs Build Websites that WIN more clients!
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Send us a Text Message. 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 Tec…
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Paul Schmidt uses Networking to WIN!
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Send us a Text Message. 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 …
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Jim Doyle WINS by Selling With A Servant Heart
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Send us a Text Message. 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…
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Jim Smith WINS By Keeping Clients Secure
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Send us a Text Message. 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 Universi…
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Scott Daigger helps Entrepreneurs WIN their battles with Online Marketing.
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Send us a Text Message. 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…
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Michael Nelson WINS by Scaling Remote Teams
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Send us a Text Message. 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, …
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David De Camillis WINS with Strategic Mergers and Marketing Innovation in Managed Services
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Send us a Text Message. 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 technolog…
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Ryan Grimes Keeps WINNING - A One Year Check In
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Send us a Text Message. 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 …
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Dustin Bolander WINs By Simplifying Cybersecurity Insurance for SMBs
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Send us a Text Message. 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 journ…
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WIN with Debbie Kestin by Unlocking the Vault of Vendor Marketing Funds
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Send us a Text Message. 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'…
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Ian Richardson Fox & Crow Perspective Before Planning In Marketing
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Send us a Text Message. 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 jou…
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Bart Justice WINS by Mastering Decision-Making with the Judgment Index and Aligning Core Values
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Send us a Text Message. 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 personali…
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Michael Cervino WINS by Navigating the Seas of Pandemic and AI in Managed Services
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Send us a Text Message. 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…
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Angela Chryplewicz WINS by Merging Family, Creativity, and Business
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Send us a Text Message. 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 recor…
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James Riley WINS by Balancing Entrepreneurship and a Successful Marriage
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Send us a Text Message. 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 sma…
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Harrison Leffel-Jones WINS by Supporting Entrepreneurs
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Send us a Text Message. 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-Mic…
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The Pumpkin Plan Helps Dave Cava's TSP Clients WIN!
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Send us a Text Message. 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 Dav…
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Embracing Remote Workforces Helps Jamison West WIN!
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Send us a Text Message. 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 busi…
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Ali Dirul WINs by Serving His Community
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Send us a Text Message. Welcome to another WIN podcast featuring an EY Entrepreneur of the Year nominee! Ali Dirul is the founder and CEO of Ryter Cooperative Industries. They are an L3C corporation - and if you don't know what that is, you're not alone! Not all state recognize low profit limited liability corporations. Tune in to learn more about …
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Maria Marin WINs by Turning Issues Into Opportunities
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Send us a Text Message. Welcome to another podcast from our EY Entrepreneur of the Year interview series. At the age of 15, war forced Maria Marin to flee from her home in Nicaragua. She immigrated to the US alone, she did not speak English, and she had $200 to her name. Fast forward many years, Maria is the founder and CEO of Unlimited Recycling a…
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Carla Ejaz WINs, WINs, WINs, no matter what!
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Send us a Text Message. This is the first interview in our EY Entrepreneur of the Year series. We're beginning with regional finalists in our local area - Michigan/Ohio. And it's an incredible story of triumph, resilience and innovation. I'm fortunate enough to have Carla Ejaz (and in subsequent interviews, both of her business partners) featured o…
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Joe Cardillo WINS by building diverse teams and new leaders!
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Send us a Text Message. You're in for a treat this week! An extra ten minutes of WINning! Joe Cardillo is the founder of The Early Manager, a coaching firm that supports job seekers and new managers. My interview with Joe went long. Really long. I learned so much about diversity, power, accountability, transparency and alignment that it was almost …
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Kathryn Rose WINs by Asking Experts for Advice
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Send us a Text Message. In 2008, Kathryn Rose went from Wall Street power broker to being an unemployed new mother and a caregiver for a sick parent almost overnight. Unable to take on a full time role, she reached out to her large network and asked what they needed help with. Someone asked her if she could help them rank on the front page of Googl…
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Ben Chappell WINs by focusing on one thing at a time.
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Send us a Text Message. Ben Chappell has had a long career in the technology space, working with both Solutions Granted (you can see Michael Crean, CEO of Solutions Granted on a previous episode of WIN) and Ingram Micro. Ben took on a new challenge, working with international technology security software application firm We Bridge. We Bridge focuse…
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Chris Johnson helps IT companies WIN with a new cybersecurity trustmark!
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Send us a Text Message. Chris Johnson is a cybersecurity compliance strategist at heart. As a former MSP, Johnson focused on helping small to mid-size businesses make the strategic IT decisions and technology implementations that improved their cybersecurity posture. He is currently CompTIA’s senior director of cybersecurity programs and ex-officio…
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Scott Cooley WINS by building a team focused on Aloha Spirit.
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Send us a Text Message. Scott Cooley started his business at the age of 13. He installed some of the first wired networks in Honolulu. Indevtech was founded in 2010, and was recently honored by Pacific Business News as one of the fastest growing companies in Hawaii. Indevtech has been growing aggressively, focused on adding new team members while m…
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Ryan Grimes WINs by showing his prospects how tech can help them WIN, too!
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Send us a Text Message. Join Carrie Richardson, partner at Richardson & Richardson consulting as she asks Ryan Grimes, CEO of My IT Indy; "What's Important Now?" Ryan started in technology back in the early 80’s when he got an Apple II with 64K of memory. No hard drive. No user interface. No operating system. He played games he built himself, spent…
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Ian Richardson WINs by focusing on growth
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Send us a Text Message. Welcome to W.I.N. (what's important now?) - the entrepreneurial podcast where we dive into business challenges, achievements, and opportunities! Join your host, Ian Richardson, from Richardson & Richardson Consulting as he explores what entrepreneurs care about and focus on. This week, Ian dives into the types of growth ever…
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Ian Richardson WINs by developing processes and documentation
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Send us a Text Message. Welcome to W.I.N. (what's important now?) - the entrepreneurial podcast where we dive into business challenges, achievements, and opportunities! Join your host, Ian Richardson, from Richardson & Richardson Consulting as he explores what entrepreneurs care about and focus on. This week, Ian reflects on the importance of devel…
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Ian Richardson WINs by helping companies strategically plan their success
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Send us a Text Message. Welcome to W.I.N. (what's important now?) - the entrepreneurial podcast where we dive into business challenges, achievements, and opportunities! Join your host, Ian Richardson, from Richardson & Richardson Consulting as he explores what entrepreneurs care about and focus on. This week, Ian dives into the services R&R have to…
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Greg Schaffer WINs by taking a holistic approach to information security
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Send us a Text Message. Welcome to W.I.N. (what's important now?) - the entrepreneurial podcast where we dive into business challenges, achievements, and opportunities! Join your host, Ian Richardson, from Richardson & Richardson Consulting as he explores what entrepreneurs care about and focus on. This week, Ian hosts Greg Schaffer, Founding Princ…
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Erica Owens WINs by providing resources and activities for families in the Detroit region
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Send us a Text Message. Welcome to W.I.N. (what's important now?) - the entrepreneurial podcast where we dive into business challenges, achievements, and opportunities! Join your host, Ian Richardson, from Richardson & Richardson Consulting as he explores what entrepreneurs care about and focus on. This week, Ian hosts Erica Owens, Founder of Fruga…
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Jennifer Brine WINs By Bringing Higher Quality Care To Those Who Need It Most
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Send us a Text Message. Welcome to W.I.N. (what's important now?) - the entrepreneurial podcast where we dive into business challenges, achievements, and opportunities! Join your host, Ian Richardson, from Richardson & Richardson Consulting as he explores what entrepreneurs care about and focus on. This week, Ian hosts Jennifer Brine, Co-Founder an…
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Anna Maria Florio WINs by pivoting during a pandemic
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Send us a Text Message. Welcome to W.I.N. (what's important now?) - the entrepreneurial podcast where we dive into business challenges, achievements, and opportunities! Join your host, Ian Richardson, from Richardson & Richardson Consulting as he explores what entrepreneurs care about and focus on. This week, Ian hosts Anna Maria Florio, the owner …
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