Ryan Caracciolo is the founder and CEO of Striventa, a business growth agency focused on helping companies move beyond isolated tactics to achieve sustainable momentum. With over a decade of experience, Ryan has built a reputation for merging strategy, smart systems, and relentless execution to help healthcare, real estate, and service-based businesses grow with measurable ROI.

In this episode, Ryan joins host Mark Osborne to discuss the evolution of marketing and sales alignment, the power of productizing services, and how his high-performance website platform, Hyperdrive WP, is transforming the way businesses approach web development. He also explores the future of SEO and AI's impact on search, revealing why strong foundations and data-driven execution will always win.

Quotes:

• "We started Striventa by striving to invent. All good ideas have a little bit of genius and a little bit of goof."

• "Marketing and sales should be held to the same return on investment. Give yourselves to the data."

• "Business needs to be agile. Owners do not want another ninety to one hundred twenty-day rebuild."

• "Just by a lateral transfer to our framework, we index about ten to fifteen percent more keywords in the first three to four weeks."

• "Websites are becoming more valuable. Those engines still need a foundation to crawl and trust."

• "Do not put a toe in every channel. Own one, build an ROI model around it, then stack."

• "If you want to A/B test twenty thousand, you cannot do ten and ten. You need twenty and twenty, or the test is not real."

Takeaways:

• Sustainable growth comes from strong foundations that align marketing, sales, and execution around shared data.

• Hyperdrive WP enables faster, scalable websites that index better and convert more efficiently.

• Productizing proven services allows agencies to deliver consistency and measurable ROI at scale.

• Focusing on bottom-funnel intent produces more qualified leads in an AI-driven search landscape.

• True testing and optimization require real budgets and disciplined commitment to accuracy.

• Businesses should dominate one marketing channel before expanding into others.

• Serving first and providing genuine value builds stronger, longer-term customer relationships.

Conclusion:

Ryan Caracciolo's insights highlight the future of modern growth strategy: unify teams, simplify execution, and productize what works. By building agile, performance-driven systems, businesses can achieve real momentum in an era where AI and constant change challenge traditional models. His approach blends pragmatism with precision—reminding founders and marketers that long-term success comes from doing the fundamentals exceptionally well.

Links Mentioned:

Website: HyperdriveWP - https://www.hyperdrivewp.com/

Agency: Striventa - https://striventa.com/

Guest Links:

LinkedIn: https://www.linkedin.com/in/ryan-caracciolo-4374a456/

Patrick McMillan is a seasoned fractional CFO and M&A advisor known in the deal community as the Q of E guy. As head of Transaction Advisory at Amplēo, he leads quality of earnings and financial due diligence engagements and collaborates with valuations, outsourced CFOs and controllers, HR, marketing, and sales tax teams across the deal life cycle. Drawing on his experience buying and selling companies and advising more than 100 transactions totaling over 2 billion dollars, Patrick explains what truly drives quality of earnings, why exit planning is good business planning, and how a quarterbacked team of advisors keeps founders aligned with their goals.

In this episode with host Mark Osborne on B2B Growth Blueprint, Patrick demystifies quality of earnings, multiples, and value acceleration. He shares practical steps owners can take in 90-day sprints to reduce risk, improve cash flow, and raise valuation while making the business easier to run today.

Quotes

• Quality could be high, medium, or low. A million dollars from one client is low quality. A million dollars from a hundred clients is high quality.

• Exit planning is good business planning because you are de-risking and tightening operations long before a deal shows up.

• You need a quarterback who aligns every advisor to the founder's goals and works in focused 90-day sprints.

Takeaways

• Quality of earnings reflects the reliability and sustainability of profits.

• Exit planning improves operations and reduces owner dependence.

• Align all advisors under a single "quarterback" to keep goals clear.

• Always be exit-ready—you never know when opportunity will knock.

Conclusion

Quality of earnings is a lens for building a stronger company now and a more valuable company later. By reducing concentration risk, improving cash to revenue proof, and aligning a cross-functional advisor team under a single quarterback, founders can move from the low end of the multiple range toward the high end while enjoying a business that runs smoother day to day. Exit readiness is simply smart, ongoing business management.

Links Mentioned

Website: Amplēo - https://ampleo.com/

Guest Links

LinkedIn Patrick McMillan: https://www.linkedin.com/in/patrickmcmillan/

Mark Osborne welcomes Daniel Feiman, founder and managing director of Build It Backwards, a consulting and training firm based in Redondo Beach, California. With a career spanning manufacturing, marketing, and commercial banking before launching his own firm nearly 30 years ago, Daniel brings a rare blend of practical operator experience and executive advisory depth. He's advised organizations across 30+ countries including Apple, Dell, Hilton, and Credit Suisse, taught at UCLA Extension for over 25 years, served as a visiting professor at the University of Huddersfield in the UK, authored four books including The Evolved Enterprise: A New Paradigm for Business Success, and holds the elite Certified Management Consultant (CMC) designation awarded to less than 1% of consultants worldwide.

In this episode, Daniel shares why "plans don't have to be perfect—just executed," and why the real ROI lies in the act of planning. He breaks down a holistic approach to succession planning that future-proofs organizations, emphasizes writing plans down to enable alignment and collaboration, and shows how leadership development, gap analyses, and individual development plans (IDPs) transform SMEs into professionally managed, resilient companies. From "building it backwards" (starting with the 20-year vision and reverse-engineering the steps) to becoming your client's "business concierge," Daniel outlines a repeatable system any growth-minded firm can adopt.

Quotes:

● "You don't need a perfect plan. What you need is a plan."

● "Proper planning prevents poor performance."

● "My worst day in consulting is still better than my best day as a banker."

Takeaways:

● Write it down. A written plan creates clarity, invites collaboration, and drives better results than ideas that live only in leaders' heads.

● Build it backwards: define the 20-year horizon, then reverse-engineer 10-, 5-, and 1-year goals with actions, owners, and metrics.

● Treat succession as organizational, not just owner exit—identify, assess, and develop leaders; use gap analyses to craft individual development plans and clear career paths.

● Professionalize to scale: move from founder-centric to team-centric by leveraging specialists and a "business concierge" mindset.

● The payoff is measurable: stronger agility, higher productivity, lower turnover, greater employee satisfaction, and a healthier bottom line.

Conclusion:

Daniel Feiman's approach reframes planning from a static document to a living process that builds alignment, agility, and bench strength. By committing to write plans down, collaborating across the organization, and "building it backwards" from a clear long-term vision, SMEs can evolve into professionally managed, future-proofed companies—ready for growth, prepared for shocks, and rich with options.

Links Mentioned:

Website: https://builditbackwards.com

Books:

• The Book on...Succession Planning Systems: The 30 Secrets To Leadership Development: https://a.co/d/0qJsevQ

• THE Book on...BUSINESS From A to Z: The 260 Most Important Answers You Need to Know (The Build It Backwards series): https://a.co/d/2NqdgxC

• The Book On Improving Productivity By Fair Means Or Foul (The Build it Backwards Series 1): https://a.co/d/bO9ad8F

Guest Links:

LinkedIn: https://www.linkedin.com/in/danielfeimanbuilditbackwards1/

Brian Samson, a three-time founder, general partner at Hangten X Capital, and host of The Nearshore Café, shares his remarkable journey from San Francisco's startup ecosystem to building thriving companies in Latin America. After discovering the resilience and adaptability of Latin American professionals, Brian recognized the region's untapped potential and began connecting U.S. businesses with exceptional LATAM talent. His story reveals how embracing volatility, cultural fluency, and creativity can turn challenges into opportunity.

He breaks down the real differences between offshoring, onshoring, and nearshoring, highlighting how same-time-zone collaboration, shared language, and mutual cultural understanding make nearshoring a powerful growth strategy. For early-stage startups and scaling businesses, nearshoring enables rapid hiring, faster product development, and greater cost efficiency—while maintaining high-quality work and strong IP protection.

Quotes:

• "When I first arrived in Argentina, I realized that in volatility lies opportunity, and within uncertainty lies incredible potential."

• "You can't just buy your way to sales. As a founder, you have a magic card that opens doors—use it before you delegate it."

• "People in Latin America grow up learning how to adapt, solve problems, and stay creative under pressure, which makes them exceptional partners for fast-moving startups."

Takeaways:

• Nearshoring bridges cultural and operational gaps by keeping teams in similar time zones while reducing costs by up to 70%.

• Latin American professionals bring unmatched adaptability, creativity, and problem-solving skills to U.S. companies.

• Founders should lead sales early on to understand the process, build the playbook, and refine messaging before scaling.

• Start small, build confidence and case studies, and grow gradually into larger markets and opportunities.

Conclusion: Brian Samson's experience demonstrates that nearshoring isn't merely a cost-saving strategy—it's a mindset shift toward smarter global collaboration. By recognizing the strength of Latin America's talent pool and combining it with founder-led initiative, startups can achieve exponential growth while maintaining agility and authenticity. His story is a blueprint for modern entrepreneurship: embrace change, stay close to your customers, and see opportunity where others see risk.

Links Mentioned: Website: https://plugg.tech

Guest Links: LinkedIn: https://www.linkedin.com/in/briansamson/

In this episode, Mark Osborne sits down with Carter Gaither, a corporate strategy and finance expert, to uncover the secrets behind successful M&A deals in today's changing market. Gaither breaks down how tariffs, interest rates, and global shifts are transforming the deal-making landscape from fast, frothy activity to strategic, cautious acquisitions.

He reveals why businesses should always be exit-ready, how to build a winning support team, and the key to positioning your company as the hero of your sale story—not just the founder.

Tune in to learn how to future-proof your business strategy and thrive in a volatile market.

Quotes:

1. "Always be ready. Always be ready."

2. "If the main character of your story is you, you're not ready."

3. "You want to be in a position where, if you get that offer, if an offer comes across the phone, you're ready, right? And you're going to get maximum value."

Takeaways:

• Always be ready to sell—operate your business as if sale is always possible.

• Reduce reliance on owners/key people; build strong teams and processes.

• Make finance/operations strategic, not just administrative.

• Use process and accountability to improve work and culture.

• M&A market is slower; patience and preparation are important. and continuity beyond any single founder.

Conclusion:

Companies should always be prepared for exit opportunities by building strong, independent teams, implementing effective processes, and treating finance as a strategic asset, especially in a challenging M&A market where patience and readiness yield the best results.

Links Mentioned:

Guest Links:

LinkedIn: https://www.linkedin.com/in/cartergaither/

Bringing an idea to life is one of the greatest challenges for founders—especially those without technical backgrounds. How do you go from concept to code without giving away half your company? How do you find the right talent, and what role does culture play in making products succeed?

Roger Einstoss, founder of Braintly, helps U.S. startups and SMBs connect with top software engineers from Latin America. Since 2013, his company has worked with global brands like Volkswagen, Nikon, and T-Mobile—helping founders bridge technical gaps, launch products, and scale efficiently. In this episode, Roger shares his insights on building tech teams, the advantages of nearshore development, and why trusting expert advisors can make or break a startup's journey.

Quotes:

1. " When you start creating a company with someone, it's like your wife or husband. You'll go through good times and bad times—so don't give away 50% of your company just because you need someone to code. "

2. " Developers in Latin America aren't robots—they'll ask why. That mindset builds better products because every line of code should solve a real problem. "

3. " Having good advisors or a coach changes everything. You need someone outside your ego who can help you see what you don't. "

4. " Founders often build an MVP that's not really an MVP. Focus only on what you need to test your idea—not on every future feature. "

Takeaways:

• Don't rush to find a technical co-founder. Many founders simply need a great developer or fractional CTO, not a permanent equity partner.

• Cultural alignment matters. Nearshore teams in Latin America offer similar time zones, strong English skills, and a collaborative mindset that enhances product outcomes.

• Trust and delegation fuel growth. Founders must focus on sales, vision, and leadership—not micromanaging button colors or minor tech details.

• Advisors accelerate progress. Working with mentors, coaches, or industry experts provides critical outside perspective and emotional balance on the entrepreneurial journey.

• Simplify your MVP. Test the core idea before building every feature; perfecting scalability can wait until you have users and feedback.

Conclusion:

Early-stage companies can achieve growth by identifying key turning points, seeking Success in startups isn't just about having a great idea—it's about execution, trust, and collaboration. By leveraging skilled nearshore talent, focusing on essentials, and surrounding yourself with the right advisors, you can turn vision into a scalable, sustainable business. As Roger puts it, "You don't have to be a superhero—you just have to build the right team."

Links Mentioned:

Guest Links:

Guest Links:

LinkedIn: Roger Einstoss - https://www.linkedin.com/in/rogereinstoss/

Website: Braintly.com - https://www.braintly.com/

Planning for the next stage of your business doesn't mean the end—it means taking control of your future. But for many founders, the thought of "exit planning" feels uncomfortable. How do you prepare to leave the company you built without losing what you've created—or yourself in the process?

Todd Krough, a seasoned Wealth Advisor at UMB Bank, brings over 30 years of experience helping business owners prepare for what's next. As President of the Exit Planning Institute's Twin Cities Chapter and a Certified Exit Planning Advisor (CEPA), Todd helps entrepreneurs understand the true value of their business, bridge the "value gap," and plan for life beyond ownership.

In this episode, Todd shares how to build a business that's both enjoyable to run and ready to sell, the importance of having a trusted advisory team, and how to approach exit planning with clarity instead of fear.

• " It's very difficult for business owners to part with their company—it's like a second or third child. That's why we say: grow or go. Either build it to where it needs to be or prepare to transition it confidently. "

• " Most owners have 90% of their wealth tied up in their business. Seeing that on paper changes everything—it gives them clarity and urgency. "

• " The most trusted advisor is often the wealth advisor, because we're there before, during, and after the sale. We see the full journey. "

• " Exit planning isn't just about selling—it's about helping a business continue, protecting employees, families, and communities. "

1. Start early and assess often. Exit planning isn't a last-minute task—it's a long-term strategy that strengthens your business today and secures your future tomorrow.

2. Understand your value gap. Many business owners don't know their true valuation. Identify how much you need for your next chapter, and whether you need to grow before you go.

3. Build a team-based approach. Coordinate your wealth advisor, CPA, attorney, and business coach so everyone is aligned. Working in silos reduces value and increases risk.

4. Prepare your business to run without you. Owner dependency scares buyers and limits freedom. Strengthen leadership and systems to make your company more sellable—and easier to manage now.

5. See your wealth beyond the business. Diversify into investments, retirement accounts, and philanthropy planning to reduce risk and increase peace of mind before and after an exit.

Exiting your business shouldn't be a rushed decision—it should be a strategic evolution. With proper planning, the right advisors, and a clear understanding of value, you can create freedom, security, and a lasting legacy. Whether you're looking to grow or go, Todd Krough reminds us: planning ahead isn't just smart business—it's peace of mind.

Guest Links: LinkedIn: Todd Krough: https://www.linkedin.com/in/todd-krough-cepa%C2%AE-66520021/ Email: [email protected] Website: UMB Bank - https://www.umb.com/

Exit Planning Institute Twin Cities Chapter: EPI Twin Cities - https://exit-planning-institute.org/chapter/epi-twin-cities-chapter

Imagine pouring everything into building a breakthrough fintech solution — only to hit a wall when it's time to sell into banks and enterprise buyers. It's not the technology holding you back… it's the go-to-market strategy. For many founders, especially technical ones, this is the painful bottleneck that stalls growth and burns investor confidence.

In this episode, Stacy Bishop — a 25+ year revenue leader in banking and financial technology — reveals what actually moves deals forward in highly regulated industries. She explains why traditional B2B playbooks often fail in fintech, and how founders can shift from "pitching features" to building trust, alignment, and momentum inside complex buying organizations.

Quotes:

1. "You can have the best product in the world — but if the bank doesn't know how to buy it, you're not getting the deal."

1. "Slow down to go fast. A thoughtful sales process accelerates revenue more than brute-force activity."

1. "Great sellers don't chase champions — they create them by simplifying the internal journey."

Takeaways:

• Winning in fintech requires process maturity, not just product innovation — buyers need a clear path to adoption and compliance.

• Discounting isn't a strategy — value clarity and stakeholder alignment close deals faster and stronger.

• The fastest-growing fintechs invest early in sales and marketing readiness, long before they feel "big enough" to do so.

Conclusion:

This conversation reminds us that enterprise success isn't about chasing every opportunity — it's about equipping customers to say yes. By prioritizing enablement, credibility, and the realities of how banks buy, fintech leaders can unlock consistent revenue growth and build companies that last.

Links Mentioned:

Website: stacybishop.com sellingfintech.kit.com/e1ec3c973c

Guest Links:

LinkedIn: https://www.linkedin.com/in/stacybishop

Imagine spending years — maybe decades — building a successful company, only to discover when you're finally ready to sell… you can't get the value you deserve. For many middle-market business owners, this is exactly what happens. Whether due to lack of preparation, unclear financials, or misalignment with investors, the dream exit can quickly become a disappointing reality.

In this episode Marc Barbeau, Vice President of Business Development at Forte One Capital, breaks down what truly drives a successful exit — especially in today's private equity-dominated market. He shares why so many owners underestimate the timing and strategic planning required, and how bringing in the right partners early can dramatically increase valuation and ensure long-term continuity for the business and its people.

Quotes:

1. "You can run a great company and still be unprepared for a sale — buyers are looking at value differently than you are."

1. "Most owners wait too long. The best exits happen when planning starts years before the decision to sell."

1. "Private equity isn't just capital — it's alignment. The right partner can take your vision further than you could alone."

Takeaways:

• Exit planning is not a transaction — it's a multi-year strategy that should align owner goals, operational readiness, and financial transparency.

• Understanding buyer priorities is key to maximizing valuation and attracting the right kind of partner.

• Private equity can be a powerful growth engine when expectations and values align from the start.

Conclusion:

This conversation highlights one essential truth: if you want a successful exit, you must think like a buyer long before you become a seller. By preparing early, investing in professional advisory, and prioritizing strategic growth, business owners can secure outcomes that honor their legacy and unlock the future they've worked so hard to build.

Links Mentioned:

Website: forteonecapital.com

Guest Links:

LinkedIn: linkedin.com/in/marc-barbeau-cepa-0386a74

Are you a founder in the $1M–$10M range, striving to scale your service-based business without giving up control or burning out? Kim Folsom, founder and CEO of Founders First Capital Partners, champions a transformative approach: helping entrepreneurs just like you gain access to growth capital, build recurring revenue, and evolve into effective business leaders. Drawing on her experience founding six startups, raising over $30 million, and supporting hundreds of founders, Kim's methods are rooted in discipline, adaptability, and continuous peer learning.

Kim stresses the importance of architecting your business for sustainable growth, harnessing systems and capital options that align with the unique journeys of women- and minority-led businesses. Her approach: set clear milestones, prioritize recurring revenue, seek the right support, and evolve your mindset as your company enters new phases.

Quotes:

1. "The importance of not just having a great idea, but the ecosystem…is key. You need to have a great distribution system to be able to scale."

1. "Setting goals—and having the discipline of weekly, monthly, quarterly reviews—is foundational."

1. "What got you here won't get you there... As companies grow, it's very important that they evolve—and evolve the advisors that they use."

Takeaways:

• Build Recurring Revenue: Move away from project-dependent business models to create stable, predictable cash flow.

• Systematize Growth: Use tested frameworks (Lean Startup, EOS) to set, review, and adapt business goals.

• Peer and Advisor Networks: Join groups of similar-stage founders to learn, grow, and "look around the corner" for what's next.

• Capital Fit: Understand all funding options—venture, revenue-based, working capital—and match them to your real needs.

• Evolve Mindset: Be willing to change your own role—and your team's—as you hit new revenue milestones.

Conclusion: By combining deliberate systems, the right capital, and growth-minded networks, founders can move beyond day-to-day survival and build thriving, sustainable businesses—without sacrificing control or vision. Kim Folsom's strategies focus on empowerment, inclusivity, and preparing service-based businesses to scale with support.

Links:

• Website: foundersfirstcapitalpartners.com

• LinkedIn: linkedin.com/in/kimtfolsom