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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 products, frameworks, methodology and process playbooks that help accelerate and deliver Digital Transformation, Cloud Adoption, DevOps and Quality Engineering solutions to our customers.

Sanjay Jupudi (along with his co-founder, Prasanna Signaruju, founded Qentelli at a Dallas based bar.  Their idea was too big for the back of a napkin - they had to borrow a piece of paper from the bartender.

Starting with Sanjay's savings of around USD 50,000 to launch the business eight years ago,  Sanjay and his team built Qentelli into a thriving debt-free business with a 9-figure valuation.    

Sanjay launched Qentelli in his basement, while also providing care for his six year old child.    Their team now exceeds 1200 employees, and their original operations and sales hires are still members of the team!

Spend some time with with Sanjay as he shares about starting a business with access to limited resources.  Sanjay discusses the sales strategies they used as a team of two, and the sales and marketing tactics they rely on now to grow from 10-50% annually.

Sanjay credits his success to extensive planning and research before exploring any new offers and idea.  Process and playbooks have been essential to their success.

Don't miss this episode of WIN!

Carrie Richardson and Ian Richardson host the WIN Podcast - What's Important Now?

They are the co-founders of Fox & Crow Group, a software development company building growth platforms for MSP and IT channel businesses.

Learn more at:

Fox & Crow Group - the MSP Sales Process platform and all-in-one CRM solution 

Fox & Crow Instinct - the MSP Decision Intelligence Platform for IT Channel Vendors

Fox & Crow Jackdaw - Competitive Intelligence Reports on Demand for MSP businesses

 
Book time with Carrie here!

Be a guest on WIN!  We host MSP channel founders, executives and sales and marketing leaders who are willing to share advice with other IT channel firms on how to build, grow or sell a business using examples from their own experience.

Send us Fan Mail

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, making them an elite managed IT services provider in the top 15% of US based MSPs.

Mr. Ahlberg shared insights into how he evaluates potential acquisitions, emphasizing the importance of cultural alignment over financial details in the early stages.

Waident's approach to vetting organizations is more art than science, focusing initially on culture rather than finances or tools. John believes that understanding the mindset and practices of a potential acquisition can reveal much about their client relationships and team dynamics. This cultural compatibility is crucial for a smooth transition post-acquisition.

Waident's M&A strategy involves a detailed 10-page protocol document developed after their second or third acquisition. This document guides the team through the process, ensuring they ask the right questions at the right time and avoid wasting time on unsuitable opportunities.

John Ahlberg advises smaller MSPs looking to be acquired to get their finances in order, ensure client profitability, and maintain thorough documentation. These steps make a company more attractive to buyers and facilitate a smoother transition.

Looking ahead to acquisition number six, John humorously notes that he's open to opportunities in warm locations like the U.S. Virgin Islands or Phoenix, aside from Chicago and Milwaukee where Waident already has a presence. He acknowledges that while they target companies with revenues between $500,000 and $2 million, the right opportunity could come from anywhere, provided the numbers make sense and there's a solid business plan in place.

In closing, Alberg emphasizes the importance of having a clear business plan and goals, both for the company and individually for team members. This forward-thinking approach not only drives growth but also ensures that Waident remains a well-structured and profitable business, ready for future opportunities.

A special thank you to Natalia Kapustina, the marketing expert who helped us pull together several great content pieces for educating the managed IT services space.  Watch for future podcasts featuring John, and some further collaborations between Carrie and John on the Fox and Crow Group website, the MSP Exit website and in the Channel Pro Network's online industry publication!

Check out John's recent interview in Channel Pro here!

Here's to 20 more years of amazing success for Waident Technology Solutions and their team!

Carrie Richardson and Ian Richardson host the WIN Podcast - What's Important Now?

They are the co-founders of Fox & Crow Group, a software development company building growth platforms for MSP and IT channel businesses.

Learn more at:

Fox & Crow Group - the MSP Sales Process platform and all-in-one CRM solution 

Fox & Crow Instinct - the MSP Decision Intelligence Platform for IT Channel Vendors

Fox & Crow Jackdaw - Competitive Intelligence Reports on Demand for MSP businesses

 
Book time with Carrie here!

Be a guest on WIN!  We host MSP channel founders, executives and sales and marketing leaders who are willing to share advice with other IT channel firms on how to build, grow or sell a business using examples from their own experience.

Send us Fan Mail

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 the technical aspects but also about empowering business owners to understand and manage cyber risks effectively.

Optimize Cyber's mission is to disseminate cybersecurity knowledge at scale, ensuring that every business owner feels equipped to handle cyber threats. The company prides itself on speaking the language of business executives rather than tech jargon, making cybersecurity comprehensible for those without a technical background. This approach allows business leaders to implement practical solutions to protect their operations from cyberattacks.

During the interview with Carrie Richardson, Matt discussed various aspects of starting and running Optimize Cyber. He shared insights into the challenges of entrepreneurship, such as the difficulty of acquiring the first few clients and the unexpected ease of handling business operations. Matt emphasized the importance of having a clear mission and adapting the company's pitch based on market feedback to find the right niche within the vast cybersecurity industry.

One of the key takeaways from the conversation was the notion that cybersecurity doesn't have to be expensive. Matt pointed out that there are many free actions businesses can take to significantly reduce the likelihood of financial loss due to cyber incidents.   If you're wondering what you can do to protect your personal or business finances from fraud, don't miss this episode of WIN!

Matt also touched upon the value of partnerships, particularly with Managed Service Providers (MSPs) and Value-Added Resellers (VARs). Optimize Cyber has established a partner program that includes both reseller and referral options, allowing other businesses to collaborate without fear of competition for clients.

In terms of growth, Matt envisions Optimize Cyber expanding its consulting and product teams, continuing to produce high-quality offerings, and educating more people about cyber risk. He underscored the importance of tracking key performance indicators like revenue, pipeline, and new opportunities to forecast and plan for the company's future.

Overall, the interview with Matt Quammen provides valuable insights into the world of cybersecurity from a business perspective. It highlights the significance of demystifying cyber risks for business leaders and offering practical, cost-effective solutions to safeguard businesses against cyber threats.

Optimize Cyber stands out as a company that prioritizes knowledge sharing and strategic partnerships to achieve its mission of enhancing cybersecurity for small businesses.

Want to be a guest on WIN?  Schedule a call with Carrie!

Carrie Richardson and Ian Richardson host the WIN Podcast - What's Important Now?

They are the co-founders of Fox & Crow Group, a software development company building growth platforms for MSP and IT channel businesses.

Learn more at:

Fox & Crow Group - the MSP Sales Process platform and all-in-one CRM solution 

Fox & Crow Instinct - the MSP Decision Intelligence Platform for IT Channel Vendors

Fox & Crow Jackdaw - Competitive Intelligence Reports on Demand for MSP businesses

 
Book time with Carrie here!

Be a guest on WIN!  We host MSP channel founders, executives and sales and marketing leaders who are willing to share advice with other IT channel firms on how to build, grow or sell a business using examples from their own experience.

Send us Fan Mail

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 Marketing, who explains how you can optimize your MSP's digital doorstep. 

He shares an in-depth analysis of over 100 MSP websites crafted strategies for success, and discusses how a perfectly placed chat can work wonders for your lead generation. 

Be prepared to take notes as we unravel the art of engaging visitors with personalized messaging that guides them smoothly from a curious click to a scheduled meeting.

We also delve into the magic behind immediate callback features and why chat support systems aren't just a 'nice-to-have' but a 'must-have' for MSPs aiming to skyrocket conversion rates. 

But wait, there's more! 

We'll take a creative detour and chat about a unique weekend project – using AI to create comic strips – and the quirky challenges of character consistency. 

Whether you're an MSP looking to beef up your online presence or just intrigued by the blend of marketing and tech, this conversation is jam-packed with anecdotes, advice, and a touch of comic relief.

Carrie Richardson and Ian Richardson host the WIN Podcast - What's Important Now?

They are the co-founders of Fox & Crow Group, a software development company building growth platforms for MSP and IT channel businesses.

Learn more at:

Fox & Crow Group - the MSP Sales Process platform and all-in-one CRM solution 

Fox & Crow Instinct - the MSP Decision Intelligence Platform for IT Channel Vendors

Fox & Crow Jackdaw - Competitive Intelligence Reports on Demand for MSP businesses

 
Book time with Carrie here!

Be a guest on WIN!  We host MSP channel founders, executives and sales and marketing leaders who are willing to share advice with other IT channel firms on how to build, grow or sell a business using examples from their own experience.

Send us Fan Mail

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 adaptability and a robust network. You'll be riveted by his candid account of starting a business during one of history's most trying periods, his evolution from a one-man operation to a thriving multimedia team, and the personal health hurdles that could have halted his journey but instead fueled his innovative spirit.

Our discussion with Paul is an inspiration to anyone navigating the business realm's ebbs and flows. Discover the fortuitous twists that led to his success, the power of community connections in Lansing - a hidden gem for entrepreneurs - and how close collaborations can blossom into lasting friendships. Whether you're a budding business owner or a seasoned professional, Paul's story underscores the importance of a supportive network and the magic that happens when you step outside your comfort zone and embrace the unpredictable path of entrepreneurship.

Carrie Richardson and Ian Richardson host the WIN Podcast - What's Important Now?

They are the co-founders of Fox & Crow Group, a software development company building growth platforms for MSP and IT channel businesses.

Learn more at:

Fox & Crow Group - the MSP Sales Process platform and all-in-one CRM solution 

Fox & Crow Instinct - the MSP Decision Intelligence Platform for IT Channel Vendors

Fox & Crow Jackdaw - Competitive Intelligence Reports on Demand for MSP businesses

 
Book time with Carrie here!

Be a guest on WIN!  We host MSP channel founders, executives and sales and marketing leaders who are willing to share advice with other IT channel firms on how to build, grow or sell a business using examples from their own experience.

Send us Fan Mail

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 media sales magnate, Jim's narrative is a testament to the power of advocacy and service in the sales industry. His personal tales not only chart the course of his impressive career but also serve as a playbook for entrepreneurs at every level grappling with the realities of business growth and customer relationships.

Stepping down from the pilot's seat of a business you've poured your heart into can be as daunting as letting your children venture into the world. Jim's candid discussions on the emotional parallels between personal evolution and professional transitions reveal an unexpected journey towards hiring a CEO and the subsequent shift in his life's focus. Listeners will find solace and guidance in Jim's reflections on how service to others and community involvement have reshaped his definition of success and purpose after his business exit.

For those navigating the labyrinth of strategic selling and complex organizational structures, this episode is a beacon. The conversation zeroes in on the art of differentiation in sales, understanding the intricate web of decision-makers, and the necessity of embracing change, including the often-feared specter of technology. Jim's insights into managing sales teams—with a nudge towards the balance between trust and control—are a treasure trove for anyone looking to refine their sales management approach and, ultimately, their sales success.

Carrie Richardson and Ian Richardson host the WIN Podcast - What's Important Now?

They are the co-founders of Fox & Crow Group, a software development company building growth platforms for MSP and IT channel businesses.

Learn more at:

Fox & Crow Group - the MSP Sales Process platform and all-in-one CRM solution 

Fox & Crow Instinct - the MSP Decision Intelligence Platform for IT Channel Vendors

Fox & Crow Jackdaw - Competitive Intelligence Reports on Demand for MSP businesses

 
Book time with Carrie here!

Be a guest on WIN!  We host MSP channel founders, executives and sales and marketing leaders who are willing to share advice with other IT channel firms on how to build, grow or sell a business using examples from their own experience.

Send us Fan Mail

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 starting a remote pharmacy concept.
• Peace Corps Experience: Managing the largest technical college in the South Pacific and developing a knack for solving problems with limited resources.
• Founding Proper Sky: How a Perl script and Craigslist helped him acquire his first clients, and the growth journey from there.
• Overcoming Major Setbacks: Losing a major client that accounted for 90% of revenue and the subsequent business challenges.
• The Importance of Coaching: The role of external advice and programs like Goldman Sachs' 10,000 Small Businesses in shaping his business acumen.
• Hiring and Building a Team: The significance of his first hires and how they contributed to the company's success.
• Future of Cybersecurity: Predictions on AI's role in cybersecurity and the importance of being prepared for cyber incidents.
• Empathy in Business: The human aspect of dealing with cyber incidents and building trust with clients.

Memorable Quotes

• Jim Smith on Entrepreneurial Resilience: "The longest, most stressful period of my entire life... there's nothing worse than laying off good people that actually are doing the work."
• On the Importance of External Help: "It taught me that it is much better to pay for good advice than it is to do it yourself in a lot of circumstances."
• Future of Cybersecurity: "As AI increases, there's going to be a counterbalance... helping organizations recover and be emotionally ready for the onslaught."

Jim Smith

• Role: Founder and CEO of Proper Sky
• Location: Philadelphia
• Background: Entrepreneurial studies at Drexel University, Peace Corps volunteer, 20+ years in the MSP industry.
• LinkedIn: Jim Smith LinkedIn

Links and Resources Mentioned

• Proper Sky: Website
• Goldman Sachs 10,000 Small Businesses Program: Website
• Adam Grant: Website
• Evolve Group: Website

Carrie Richardson and Ian Richardson host the WIN Podcast - What's Important Now?

They are the co-founders of Fox & Crow Group, a software development company building growth platforms for MSP and IT channel businesses.

Learn more at:

Fox & Crow Group - the MSP Sales Process platform and all-in-one CRM solution 

Fox & Crow Instinct - the MSP Decision Intelligence Platform for IT Channel Vendors

Fox & Crow Jackdaw - Competitive Intelligence Reports on Demand for MSP businesses

 
Book time with Carrie here!

Be a guest on WIN!  We host MSP channel founders, executives and sales and marketing leaders who are willing to share advice with other IT channel firms on how to build, grow or sell a business using examples from their own experience.

Send us Fan Mail

 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 healthcare sector to the helm of his own successful web enterprise. His tale is a testament to the power of strategic freelancing, the art of team stewardship, and the foresight to leverage platforms like Upwork in the quest for growth.

Navigating the web development seas is no small feat, especially with the tide of artificial intelligence reshaping its shores. In this episode, Scott and I explore the evolving landscape where AI's role in content creation and design is burgeoning yet still demands the nuanced human touch for understanding client needs. As we consider how AI might influence the economics of the industry, we also contrast the investment strategies of bootstrapped small businesses against their deep-pocketed corporate counterparts. It's a compelling look into how today's developers must adapt to not only technological advances but also to the diverse fiscal priorities of their clientele.

Lastly, Scott imparts the wisdom gleaned from his MBA journey, underscoring the invaluable lessons of entrepreneurship and the crucial mindset shifts required for business success. His practical advice for budding businesses aiming to carve out their digital space is nothing short of golden—clarity in vision, the significance of rapport, and the collaborative relationship between client and developer. 

Wrapping up, we reflect on the potential future of AI in design, leaving us with an eager anticipation of what's to come. Join us for this insightful session, as we merge the technical with the entrepreneurial spirit, right here on WIN.

Carrie Richardson and Ian Richardson host the WIN Podcast - What's Important Now?

They are the co-founders of Fox & Crow Group, a software development company building growth platforms for MSP and IT channel businesses.

Learn more at:

Fox & Crow Group - the MSP Sales Process platform and all-in-one CRM solution 

Fox & Crow Instinct - the MSP Decision Intelligence Platform for IT Channel Vendors

Fox & Crow Jackdaw - Competitive Intelligence Reports on Demand for MSP businesses

 
Book time with Carrie here!

Be a guest on WIN!  We host MSP channel founders, executives and sales and marketing leaders who are willing to share advice with other IT channel firms on how to build, grow or sell a business using examples from their own experience.

Send us Fan Mail

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 candid story is a masterclass in resilience and adaptability in the unpredictable tech industry. 

Alongside Michael, we unravel the hard decisions that come with entrepreneurship, like narrowing client focus and managing client dependencies for sustained profitability. His narrative is not just about facing challenges but about overcoming them with strategic insight and unwavering determination.

The world of work has undergone a seismic shift, and our conversation with Michael sheds light on the transition from traditional office spaces to the domain of remote work. 

As a once skeptical business owner, he shares his transformation into a staunch advocate for remote teams, witnessing firsthand the exceptional productivity and cultural synergy of virtual employees. 

We dissect the distinctions between outsourcing and staff augmentation, revealing how dedicated remote staff can become the lifeblood of a company's operations. Plus, we'll guide you through the considerations for businesses contemplating the leap into staff augmentation, with Scaled poised as your indispensable HR ally.

Finally, we delve into the legalities and market dynamics of the tech job market, from determining contractor versus employee status to navigating unemployment insurance claims. 

The impact of COVID-19 has revolutionized not only remote employment but also opened doors to global talent. 

Reflecting on my own experience with considering hiring abroad, we tackle common misconceptions about outsourcing, emphasizing efficiency and work ethic over mere cost savings. 

We wrap up by examining shifts in hiring practices that have rejigged the employee-employer power balance, influencing workplace discipline and accountability. For those ready to amplify their IT capabilities, Michael's insights provide a roadmap to scaling teams with competent, enthusiastic professionals.

Carrie Richardson and Ian Richardson host the WIN Podcast - What's Important Now?

They are the co-founders of Fox & Crow Group, a software development company building growth platforms for MSP and IT channel businesses.

Learn more at:

Fox & Crow Group - the MSP Sales Process platform and all-in-one CRM solution 

Fox & Crow Instinct - the MSP Decision Intelligence Platform for IT Channel Vendors

Fox & Crow Jackdaw - Competitive Intelligence Reports on Demand for MSP businesses

 
Book time with Carrie here!

Be a guest on WIN!  We host MSP channel founders, executives and sales and marketing leaders who are willing to share advice with other IT channel firms on how to build, grow or sell a business using examples from their own experience.

Send us Fan Mail

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 while maintaining the unique identity of each entity.

In a candid exchange, David imparts wisdom gleaned from the successful union of Platte River and Applied Tech, highlighting the significance of a robust integration strategy and the power of a harmonized operational framework. As we dissect the critical role of branding and consistent communication, learn how to minimize client fallout and staff resistance during these transformative business ventures.

The conversation takes a dynamic turn with the overview of TechMedics' evolution, spurred by a chance encounter that turned into a thriving partnership. 

Consider the realities of digital marketing and content creation as we scrutinize their impact on visibility and lead generation, affirming the necessity of a meticulously crafted annual marketing plan. 

This podcast about brand development and growth strategies culminates with an optimistic glimpse into the future of marketing in our industry. Be inspired by David's relentless pursuit of innovation at TechMedics and the marketing feats that await. 

Join us to gain a wealth of knowledge that could propel your business into its next chapter of success.

Carrie Richardson and Ian Richardson host the WIN Podcast - What's Important Now?

They are the co-founders of Fox & Crow Group, a software development company building growth platforms for MSP and IT channel businesses.

Learn more at:

Fox & Crow Group - the MSP Sales Process platform and all-in-one CRM solution 

Fox & Crow Instinct - the MSP Decision Intelligence Platform for IT Channel Vendors

Fox & Crow Jackdaw - Competitive Intelligence Reports on Demand for MSP businesses

 
Book time with Carrie here!

Be a guest on WIN!  We host MSP channel founders, executives and sales and marketing leaders who are willing to share advice with other IT channel firms on how to build, grow or sell a business using examples from their own experience.