09: From Coffee Brand Success to Corporate Governance Mastery: Joshua Maidan on Scaling and Exiting Right

From Angel To Exit

#Entrepreneur #Business #Bruce Eckfeldt

26:28

Squid Game is back—and this time, the knives are out. In the thrilling Season 3 premiere, Player 456 is spiraling and a brutal round of hide-and-seek forces players to kill or be killed. Hosts Phil Yu and Kiera Please break down Gi-hun’s descent into vengeance, Guard 011’s daring betrayal of the Game, and the shocking moment players are forced to choose between murdering their friends… or dying. Then, Carlos Juico and Gavin Ruta from the Jumpers Jump podcast join us to unpack their wild theories for the season. Plus, Phil and Kiera face off in a high-stakes round of “Hot Sweet Potato.” SPOILER ALERT! Make sure you watch Squid Game Season 3 Episode 1 before listening on. Play one last time. IG - @SquidGameNetflix X (f.k.a. Twitter) - @SquidGame Check out more from Phil Yu @angryasianman , Kiera Please @kieraplease and the Jumpers Jump podcast Listen to more from Netflix Podcasts . Squid Game: The Official Podcast is produced by Netflix and The Mash-Up Americans.…

about a year ago 44:12

MP3•Episode home

In this episode of From Angel to Exit, Bruce Eckfeldt speaks with entrepreneur and investor Joshua Maidan, whose journey from Colombia to New York led to the creation of a high-end coffee brand with international acclaim. Maidan shares how he scaled the business using real estate savvy, aggressive strategy, and deep operational structure. The episode centers on how misaligned visions and lack of corporate governance led to a pivotal exit—and how those lessons now guide his investment philosophy and deal execution.

Key Takeaways

Corporate governance is vital from day one—misalignment can kill promising ventures.
A shared brand vision must be backed by aligned operating agreements.
Clear exit mechanisms save time, stress, and future litigation risk.
High design and product quality can’t overcome partner misalignment.
Early board involvement separates day-to-day operations from strategy.
Documented roles and responsibilities avoid equity vs. contribution conflicts.
External investors bring discipline—and force professional governance.
Strong operational systems and clarity make exits seamless and scalable.

Links & Resources

Joshua Maidan
- https://www.linkedin.com/in/joshuamaidan
Subscribe to the Podcast:
- Find From Angel to Exit on Apple Podcasts, Spotify, Google Podcasts, or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode.
Newsletter & Exclusive Content:
- Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates.
Connect with Bruce & the Community:
- LinkedIn: Bruce Eckfeldt
- Instagram: @bruce_eckfeldt
- Email:
  - podcast@eckfeldt.com
  - bruce@eckfeldt.com

17 episodes

From Angel To Exit

09: From Coffee Brand Success to Corporate Governance Mastery: Joshua Maidan on Scaling and Exiting Right

From Angel To Exit

published about a year ago

MP3•Episode home

Key Takeaways

Corporate governance is vital from day one—misalignment can kill promising ventures.
A shared brand vision must be backed by aligned operating agreements.
Clear exit mechanisms save time, stress, and future litigation risk.
High design and product quality can’t overcome partner misalignment.
Early board involvement separates day-to-day operations from strategy.
Documented roles and responsibilities avoid equity vs. contribution conflicts.
External investors bring discipline—and force professional governance.
Strong operational systems and clarity make exits seamless and scalable.

Links & Resources

Joshua Maidan
- https://www.linkedin.com/in/joshuamaidan
Subscribe to the Podcast:
- Find From Angel to Exit on Apple Podcasts, Spotify, Google Podcasts, or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode.
Newsletter & Exclusive Content:
- Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates.
Connect with Bruce & the Community:
- LinkedIn: Bruce Eckfeldt
- Instagram: @bruce_eckfeldt
- Email:
  - podcast@eckfeldt.com
  - bruce@eckfeldt.com

17 episodes

#Entrepreneur #Business #Bruce Eckfeldt

All episodes

From Angel To Exit

1
16: Inside 47 Acquisitions: What Experienced Buyers Look for in a Successful Acquisition 39:25

2 days ago39:25

39:25

David Turner, CEO of Velocity Now and former CRO at IHS, joins the show to unpack what truly drives successful business exits. With firsthand experience leading 47 acquisitions and scaling IHS from $320M to $1.8B, David offers rare insight into the buyer’s mindset. Founders will gain actionable strategies to prepare for sale, avoid common missteps, and understand how to position their company for maximum value. Key Takeaways Acquirers often buy because they’re struggling with organic growth. Private equity buyers face increasing pressure from extended fund cycles. Founders must dilute their own delusion about earn-outs and post-sale roles. Most successful acquisitions start with strong personal rapport at the leadership level. Presenting all risks upfront builds credibility and avoids downstream surprises. Tell your company story consistently—long before you plan to sell. Time kills deals; speed and decisiveness are critical on both sides. Due diligence always finds skeletons; buyers care more about how you handle them. Key Takeaways Family dynamics require careful navigation during succession and sale Building to sell starts with solid operational foundations and leadership structure Industry shifts demand business model agility and innovation Emotional resilience is critical for founder wellbeing and decision-making Strong relationships and reputation can drive organic exit opportunities Certifications and social responsibility increase buyer appea Timing the exit strategically is as important as structuring the deal Post-exit identity clarity eases the transition into new ventures Links & Resources David Turner Website: http://velocitynowllc.com/ Email: david@velocitynowllc.com Subscribe to the Podcast: Find From Angel to Exit on Apple Podcasts , Spotify , Google Podcasts , or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode. Newsletter & Exclusive Content: Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates. Connect with Bruce & the Community: LinkedIn: Bruce Eckfeldt Instagram: @bruce_eckfeldt Email: podcast@eckfeldt.com bruce@eckfeldt.com…

From Angel To Exit

1
15: How Leslie Adams Scaled and Sold a Multi-Generational Scrap Metal Business 44:59

9 days ago44:59

44:59

In this episode, Leslie Kraatz Adams shares the remarkable journey of scaling and exiting Federal Metals, a third-generation scrap metal business. Starting with deep family roots and evolving industry dynamics, Leslie transformed the company from a local scrapyard into a major regional player in Western Canada. She candidly discusses leadership challenges, navigating family dynamics, preparing for sale, and her pivot into health and wellness entrepreneurship with her new venture, At Work of Heart. Key Takeaways Family dynamics require careful navigation during succession and sale Building to sell starts with solid operational foundations and leadership structure Industry shifts demand business model agility and innovation Emotional resilience is critical for founder wellbeing and decision-making Strong relationships and reputation can drive organic exit opportunities Certifications and social responsibility increase buyer appea Timing the exit strategically is as important as structuring the deal Post-exit identity clarity eases the transition into new ventures Links & Resources Leslie Kraatz Adams CWebsite: https://aworkofheart.ca LinkedIn: https://www.linkedin.com/in/lesliekraatz/ Subscribe to the Podcast: Find From Angel to Exit on Apple Podcasts , Spotify , Google Podcasts , or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode. Newsletter & Exclusive Content: Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates. Connect with Bruce & the Community: LinkedIn: Bruce Eckfeldt Instagram: @bruce_eckfeldt Email: podcast@eckfeldt.com bruce@eckfeldt.com…

From Angel To Exit

1
14: Inside a Rapid M&A Deal: How Calvin Johnson Prepared Lykki for a Fortune 500 Exit 40:11

16 days ago40:11

40:11

From washing cars as a teen to selling a business with over $290M in sales, Calvin Johnson’s entrepreneurial journey is nothing short of remarkable. In this episode, Calvin shares how he built and exited Lykki, an office supply and coffee delivery company, and the key lessons he learned around culture, technology, and timing. Founders looking to scale smart and exit well will gain real-world insights into M&A strategy, deal preparation, and post-exit purpose. Key Takeaways Start building your M&A data vault 1–2 years in advance for deal-readiness Culture-first hiring and top-tier talent drive long-term operational success Combining related services (coffee + supplies) can create a defensible market edge Earnouts often underdeliver—opt for cash deals when possible A top-notch M&A lawyer is more valuable than a flashy M&A firm Understanding your acquirer’s needs can dramatically increase valuation Exiting a business doesn’t mean retiring—plan a purpose-driven next chapter Post-exit, your identity may shift—prepare emotionally, not just financially Links & Resources Calvin Johnson ClubNeed (Social Giving Platform): clubneed.org ClubNeed Travel (Impact Travel Trips): clubneedtravel.com Subscribe to the Podcast: Find From Angel to Exit on Apple Podcasts , Spotify , Google Podcasts , or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode. Newsletter & Exclusive Content: Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates. Connect with Bruce & the Community: LinkedIn: Bruce Eckfeldt Instagram: @bruce_eckfeldt Email: podcast@eckfeldt.com bruce@eckfeldt.com…

From Angel To Exit

1
13: Inside Cannabis Private Equity: Scalable Models, Smart Terms, and Investor Strategy 36:58

23 days ago36:58

36:58

In this episode, Bruce Eckfeldt interviews Jordan Youkilis, founding partner of Key Investment Partners, to explore how cannabis investing offers unique challenges and opportunities for founders. Jordan shares his journey from traditional finance to cannabis private equity, highlighting lessons in capital deployment, deal structuring, and scaling businesses in tightly regulated environments. Key Takeaways Profitable, cash-flow-positive cannabis businesses attract more investor interest than high-growth, unprofitable ones Capital scarcity in cannabis allows investors to negotiate better terms and lower valuations Section 280E taxes heavily penalize cannabis businesses, affecting valuation and deal viability Strong due diligence processes and institutional-grade practices enhance investor confidence Founders must plan capital raises 12–18 months in advance, especially in tight funding markets Misjudging market cycles and over-raising can lead to damaging down rounds Understanding investor fund cycles helps founders better tailor pitches and timing Warm introductions and strategic networking greatly improve investment access Links & Resources Jordan Youkilis Website: keyinvestmentpartners.com LinkedIn: Jordan Youkilis Podcast: Cannabis Unlocked Subscribe to the Podcast: Find From Angel to Exit on Apple Podcasts , Spotify , Google Podcasts , or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode. Newsletter & Exclusive Content: Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates. Connect with Bruce & the Community: LinkedIn: Bruce Eckfeldt Instagram: @bruce_eckfeldt Email: podcast@eckfeldt.com bruce@eckfeldt.com…

From Angel To Exit

1
12: Lessons from Four Exits: How Pete Martin Built, Scaled, and Sold Without Regrets 44:34

4 weeks ago44:34

44:34

Serial entrepreneur Pete Martin joins the show to unpack his journey across four business exits, including a standout 12x EBITDA sale to KPMG. Drawing from both personal and professional highs and lows, Pete shares powerful lessons on building scalable, values-driven companies, designing for exit, and avoiding the common pitfalls that sabotage founder success. From crafting a cultural manifesto to structuring clean financials, this episode is a masterclass in M&A readiness for founder-CEOs. Key Takeaways Design your business to function without you to enable a clean exit. Culture alignment with employees and clients directly impacts scalability. Strong financial controls are critical—reviewed and audited books build buyer confidence. Pre-exit partnerships with potential acquirers can significantly boost valuation. Declining misaligned clients reinforces culture and attracts better opportunities. Prepare for the worst in partnerships with clear buy-sell agreements. Retention plans and bonus structures smooth transitions during acquisitions. Non-founders driving revenue make earn-out-free deals possible. Links & Resources Pete Martin www.askmyboard.com https://scaleupfaster.com/ https://www.linkedin.com/in/petegmartin/ pmartin@askmyboard.com Subscribe to the Podcast: Find From Angel to Exit on Apple Podcasts , Spotify , Google Podcasts , or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode. Newsletter & Exclusive Content: Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates. Connect with Bruce & the Community: LinkedIn: Bruce Eckfeldt Instagram: @bruce_eckfeldt Email: podcast@eckfeldt.com bruce@eckfeldt.com…

From Angel To Exit

1
11: How Alan McLaren Scaled Two Agencies, Built a Personal Branding Powerhouse, and Prepped for Exit 35:55

5 weeks ago35:55

35:55

Alan McLaren, co-founder of Strata Originals, shares his journey from corporate leadership to entrepreneurial success. In this episode, he reveals how he scaled two marketing agencies, built a powerful personal branding firm, and supports founders preparing for strategic business exits. Alan discusses M&A readiness, founder well-being, and how personal branding plays a crucial role in business growth and exit strategies. Key Takeaways Corporate experience builds foundational skills, but entrepreneurship demands creativity and flexibility. Aligning values is critical to sustaining long-term business partnerships. Business exits are emotionally complex—founders must prepare mentally, not just financially. Personal branding helps founder-CEOs drive visibility, valuation, and thought leadership. Successful M&A requires operational performance and expectation management through the entire deal. Founders must prioritize health, relationships, and purpose to avoid post-exit burnout. Defensible calendars protect time and focus across business and personal priorities. Leaders who invest in people—not just transactions—enjoy deeper, lasting success. Links & Resources Alan McLaren www.strataoriginals.com LinkedIn - Alan McLaren Subscribe to the Podcast: Find From Angel to Exit on Apple Podcasts , Spotify , Google Podcasts , or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode. Newsletter & Exclusive Content: Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates. Connect with Bruce & the Community: LinkedIn: Bruce Eckfeldt Instagram: @bruce_eckfeldt Email: podcast@eckfeldt.com bruce@eckfeldt.com…

From Angel To Exit

1
01: From Founding to Exit: Scaling Mass Communications and Life After 44:42

6 weeks ago44:42

44:42

In this episode of From Angel to Exit, host Bruce Eckfeldt sits down with Darren Mass, the founder of Mass Communications, to discuss his entrepreneurial journey from launch to acquisition. Darren shares how his early fascination with engineering led him to build a successful telecom company, the strategies he used to scale, and the key decision points that led to a $40 million exit. He also reflects on life post-sale, the challenges of transitioning from CEO to employee, and his new mission helping entrepreneurs navigate growth and exit planning. Key Takeaways: Scale your company by thinking and acting like the CEO of a $10M+ business from the start. Prioritize teamwork and avoid CEO ego—build a strong team that drives success. Always be open to discussing an exit, but ensure the timing and valuation align with your goals. Identify early warning signs of burnout or stagnation to determine the right time to sell. An exit is just the beginning—have a plan for your next move before the deal closes. Money alone doesn’t create happiness; purpose and relevance post-exit are crucial. Entrepreneurs should define whether they’re running a lifestyle or growth business early on. Use LinkedIn strategically—it’s a vital platform for networking, brand-building, and business growth. Resources & Links Darren Mass https://www.linkedin.com/in/darrenmass/ https://joinbrandbuilt.com/join563688 Subscribe to the Podcast: Find From Angel to Exit on Apple Podcasts , Spotify , Google Podcasts , or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode. Newsletter & Exclusive Content: Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates. Connect with Bruce & the Community: LinkedIn: Bruce Eckfeldt Instagram: @bruce_eckfeldt Email: podcast@eckfeldt.com bruce@eckfeldt.com…

From Angel To Exit

1
02: Unlocking the Second Bite: Maximizing Business Exits with Todd Taskey 47:06

6 weeks ago47:06

47:06

Todd Taskey, an M&A advisor and angel investor, joins Bruce Eckfeldt to discuss the nuances of business exits and private equity partnerships. Taskey explains the importance of structuring deals to optimize cash, equity, and earnouts. He highlights how founders can use a sale to accelerate growth rather than just exit, and shares real-world examples of successful second-bite opportunities. This episode is packed with strategic insights for founders looking to navigate the complexities of M&A and maximize the value of their business sale. Key Takeaways: Founders should distinguish between exiting a business and using a sale to accelerate growth. The best deals balance cash, equity, and earnout structures to optimize long-term returns. Private equity partnerships can provide strategic advantages, but founders must ensure transparency in equity and debt arrangements. Overstating future projections can backfire, making it crucial to present realistic financial expectations. Retaining equity in a larger company can be a lucrative strategy for entrepreneurs who want to stay involved post-sale. The right buyer fit—culturally and strategically—is just as important as financial terms. Business owners should have GAP-compliant financials and proper accounting structures in place before seeking a sale. Understanding different private equity models helps founders negotiate better terms and avoid common pitfalls. Links & Resources Todd Taskey https://potomacbusinesscapital.com/podcast/ https://www.linkedin.com/in/toddtaskey https://potomacbusinesscapital.com/ todd@potomacbusinesscapital.com Subscribe to the Podcast: Find From Angel to Exit on Apple Podcasts , Spotify , Google Podcasts , or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode. Newsletter & Exclusive Content: Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates. Connect with Bruce & the Community: LinkedIn: Bruce Eckfeldt Instagram: @bruce_eckfeldt Email: podcast@eckfeldt.com bruce@eckfeldt.com…

From Angel To Exit

1
03: From Clarity to Close: Strategizing Your Ideal Business Exit with Suren Kapse 38:37

6 weeks ago38:37

38:37

In this episode of From Angel to Exit , Bruce Eckfeldt speaks with Suren Kapse, a seasoned advisor and coach specializing in M&A and exit strategies. Suren shares hard-earned insights on how founders can prepare for successful exits, whether selling for people, assets, scale, or client access. He also unpacks how buyers evaluate cultural fit, valuation dynamics, and when to go international. A must-listen for CEOs planning to scale or exit. Key Takeaways Exit planning starts with personal clarity—know your “why” before choosing an exit route. Buyers typically acquire for people, scale, clients, or strategic assets. Know your leverage. Successful exits take 18–36 months of prep: align metrics, clean financials, and position properly. Study past deals to model your business around what buyers are actively acquiring. Cultural alignment is critical—mismatched values derail integrations post-deal. Founders should consider international buyers who may value U.S. assets more aggressively. Use AI-powered search tools to find under-the-radar acquisition targets as a buyer. Market timing matters—monitor industry cycles and valuation trends before you sell. Links & Resources Suren Kapse https://www.linkedin.com/in/suren-kapse/ https://aptculture.com/ suren@aptculture.com Subscribe to the Podcast: Find From Angel to Exit on Apple Podcasts , Spotify , Google Podcasts , or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode. Newsletter & Exclusive Content: Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates. Connect with Bruce & the Community: LinkedIn: Bruce Eckfeldt Instagram: @bruce_eckfeldt Email: podcast@eckfeldt.com bruce@eckfeldt.com…

From Angel To Exit

1
04: How Shawn Freeman Scaled an MSP to $5M and Exited at 1.4x Revenue 44:48

6 weeks ago44:48

44:48

Shawn Freeman, founder of a successful managed service provider (MSP), joins Bruce Eckfeldt to share his journey from launching a tech side hustle to scaling a $5M business and executing a 1.4x revenue exit. He reflects on key inflection points in leadership, recurring revenue strategy, and the emotional and operational complexities of being acquired. Shawn’s insights are essential for founder-CEOs preparing for strategic exits. Key Takeaways Recurring revenue is essential for building valuation and predictable growth. Exit readiness includes tax planning and proper corporate structure from day one. Leadership means getting out of your own way and empowering others. Always assume key employees may leave—design systems that don’t rely on them. Company culture must be intentional, with clear values and psychological safety. Be cautious of acquirers unwilling to adapt or integrate new ideas. Involve your leadership team early in potential exit conversations. A premium service model requires aligned pricing and long-term thinking. Links & Resources Shawn Freeman https://leaderstechacademy.com/ https://www.linkedin.com/in/shawnfreeman-/ Subscribe to the Podcast: Find From Angel to Exit on Apple Podcasts , Spotify , Google Podcasts , or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode. Newsletter & Exclusive Content: Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates. Connect with Bruce & the Community: LinkedIn: Bruce Eckfeldt Instagram: @bruce_eckfeldt Email: podcast@eckfeldt.com bruce@eckfeldt.com…

From Angel To Exit

1
05: From Bootstrap to Buyout: Scaling Tech Startups with Strategic Go-to-Market and Exit Fit 49:54

6 weeks ago49:54

49:54

In this episode of From Angel to Exit, Bruce Eckfeldt speaks with serial entrepreneur Shreesha Ramdas about his journey from risk-averse engineer to founder of multiple successful startups. Shreesha shares his unique “startup fitness” framework, lessons from bootstrapping LeadFormix through to its acquisition by SAP, and his current work with Lumber, a workforce optimization platform for the construction industry. Founders will gain deep insight into scaling deliberately, building with an exit in mind, and leveraging partnerships for strategic growth. Key Takeaways: Don’t build for an exit—build for value; exits follow strong growth trajectories. Develop sales and cross-functional exposure early to become a well-rounded founder. Use the “startup fitness” framework to navigate each phase of startup growth methodically. Identify and engage potential acquirers early through partnerships, not pitches. Bootstrap when possible to stay close to customer pain points and retain control. Keep an organized data room from day one—be always ready for diligence. Avoid open-source licensing pitfalls that can derail acquisition deals. Invest in company culture and cross-functional hires from the outset for scalable execution. Links & Resources Shreesha Ramdas LinkedIn: linkedin.com/in/shreesharamdas Subscribe to the Podcast: Find From Angel to Exit on Apple Podcasts , Spotify , Google Podcasts , or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode. Newsletter & Exclusive Content: Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates. Connect with Bruce & the Community: LinkedIn: Bruce Eckfeldt Instagram: @bruce_eckfeldt Email: podcast@eckfeldt.com bruce@eckfeldt.com…

From Angel To Exit

1
06: From Side Hustle to Strategic Exit: Lessons from Scaling Unique World 44:44

6 weeks ago44:44

44:44

In this episode of From Angel to Exit , host Bruce Eckfeldt sits down with Eddie Geller, serial entrepreneur and founder of Unique World, to unpack the gritty, insightful journey from launching early web services to a high-stakes M&A exit. Geller candidly shares the highs and lows of scaling a business, from client concentration pitfalls to post-acquisition culture clashes. This episode is rich with takeaways for founder-CEOs aiming to build, scale, and eventually exit their businesses strategically and successfully. Key Takeaways Declining a $30M offer taught the importance of realistic valuations and market timing. Relying on a single client base can cripple a business—diversification is key. Open-book management rebuilt trust and performance post-2008 crash. A company must be operationally independent from its founder to be sellable. Hiring based on assumed influence, not proven impact, can backfire. All-cash deals require clean operations and attractive growth metrics. Cultural mismatch post-acquisition can derail team retention and value. Measuring culture (via SKOR) can be a driver of business performance. Links & Resources Eddie Geller https://www.linkedin.com/in/eddiegeller/ https://www.cultureskor.com/ Subscribe to the Podcast: Find From Angel to Exit on Apple Podcasts , Spotify , Google Podcasts , or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode. Newsletter & Exclusive Content: Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates. Connect with Bruce & the Community: LinkedIn: Bruce Eckfeldt Instagram: @bruce_eckfeldt Email: podcast@eckfeldt.com bruce@eckfeldt.com…

From Angel To Exit

1
07: Lessons from a Failed M&A to a Successful Exit: The Founder Story Behind ClassTag 44:21

6 weeks ago44:21

44:21

In this compelling episode of From Angel to Exit , Bruce Eckfeldt interviews Vlada Lotkina, founder of ClassTag, an EdTech platform that transformed parent-teacher communication. From her entrepreneurial upbringing in Ukraine to a successful exit in the U.S., Vlada shares the challenges of monetizing in the K-12 sector, navigating a failed M&A, and rethinking her strategy for venture number two. Founder-CEOs will find inspiration and pragmatic lessons in her candid account of scaling a mission-driven business with resilience and clarity. Key Takeaways Personal conviction helped validate the problem when initial feedback was discouraging. Early MVP failures taught resilience and forced creative pivots in product strategy. Growth came through teachers marketing to teachers—not parents. The business scaled with a unique media model, later bolstered by SaaS. A failed M&A taught the importance of running the business regardless of deal progress. Private equity deals often depend on external fund dynamics, not founder value. Exiting with minimal earn-out allowed smoother transition and founder relief. Future ventures are now guided by “following the money” and co-founder alignment. Links & Resources Vlada Lotkina https://www.linkedin.com/in/vlada-lotkina/ vlada@elev8orlab.com https://www.elev8orlab.com/ Subscribe to the Podcast: Find From Angel to Exit on Apple Podcasts , Spotify , Google Podcasts , or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode. Newsletter & Exclusive Content: Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates. Connect with Bruce & the Community: LinkedIn: Bruce Eckfeldt Instagram: @bruce_eckfeldt Email: podcast@eckfeldt.com bruce@eckfeldt.com…

From Angel To Exit

1
08: Inside Middle Market M&A: What Every Business Owner Must Know Before Selling 43:13

6 weeks ago43:13

43:13

In this sharp and candid episode of From Angel to Exit , Bruce Eckfeldt interviews Bill Snow, Managing Director at Focus Investment Banking and author of several books on M&A. With nearly two decades of experience in the middle market, Bill shares blunt truths and practical advice on what it really takes to sell a business. From valuation myths to private equity dynamics, this episode is packed with critical insights for founder-CEOs planning to scale and exit. Key Takeaways Clearly define your exit goals—buyers respond to clarity and purpose. Make yourself as founder expendable—owner dependency kills valuation. Strategic buyers pay premiums when synergies solve their core problems. Poor inventory and AR management can erode deal value by millions. A strong, experienced M&A attorney is essential to avoid costly delays. Most deals fail due to underperformance during the sales process. Working capital calculations are critical—don’t underestimate the details. The ideal exit process takes ~9 months; rushing invites risk and error. Links & Resources Bill Snow https://www.billsnow.com https://www.focusbankers.com https://www.linkedin.com/in/billsnow/ Subscribe to the Podcast: Find From Angel to Exit on Apple Podcasts , Spotify , Google Podcasts , or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode. Newsletter & Exclusive Content: Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates. Connect with Bruce & the Community: LinkedIn: Bruce Eckfeldt Instagram: @bruce_eckfeldt Email: podcast@eckfeldt.com bruce@eckfeldt.com…

From Angel To Exit

1
09: From Coffee Brand Success to Corporate Governance Mastery: Joshua Maidan on Scaling and Exiting Right 44:12

6 weeks ago44:12

44:12

In this episode of From Angel to Exit , Bruce Eckfeldt speaks with entrepreneur and investor Joshua Maidan, whose journey from Colombia to New York led to the creation of a high-end coffee brand with international acclaim. Maidan shares how he scaled the business using real estate savvy, aggressive strategy, and deep operational structure. The episode centers on how misaligned visions and lack of corporate governance led to a pivotal exit—and how those lessons now guide his investment philosophy and deal execution. Key Takeaways Corporate governance is vital from day one—misalignment can kill promising ventures. A shared brand vision must be backed by aligned operating agreements. Clear exit mechanisms save time, stress, and future litigation risk. High design and product quality can’t overcome partner misalignment. Early board involvement separates day-to-day operations from strategy. Documented roles and responsibilities avoid equity vs. contribution conflicts. External investors bring discipline—and force professional governance. Strong operational systems and clarity make exits seamless and scalable. Links & Resources Joshua Maidan https://www.linkedin.com/in/joshuamaidan Subscribe to the Podcast: Find From Angel to Exit on Apple Podcasts , Spotify , Google Podcasts , or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode. Newsletter & Exclusive Content: Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates. Connect with Bruce & the Community: LinkedIn: Bruce Eckfeldt Instagram: @bruce_eckfeldt Email: podcast@eckfeldt.com bruce@eckfeldt.com…

From Angel To Exit

1
10: Behind the Exit: Lessons from Ross Shanken’s Nine-Figure Journey with Jornaya 51:41

6 weeks ago51:41

51:41

Ross Shanken, founder and former CEO of Jornaya, shares the story behind building a pioneering lead verification platform and guiding it to a nine-figure exit. In this episode of From Angel to Exit , Ross unpacks the strategic frameworks, operational challenges, and personal insights that fueled his success—from initial market entry to final acquisition. It's a must-listen for founder-CEOs aiming to scale confidently and exit smartly. Key Takeaways Establish your financial model early and revisit it often to inform strategic decisions. Align your leadership team using shared vision exercises like “headline planning.” Avoid exiting on investor-driven timelines—run your own deal process. Bring on key roles (like CFO) earlier than you think you need them. Use backcasting: start from your ideal exit and work backwards operationally. Honest internal dialogue creates stronger strategic alignment and execution. Validate your market thesis with early feedback loops from prospective acquirers. Sitting in discomfort post-exit can be a powerful period of personal growth. Links & Resources Ross Shanken https://www.linkedin.com/in/rossshanken/ www.vojomo.com ross@vojomo.com Subscribe to the Podcast: Find From Angel to Exit on Apple Podcasts , Spotify , Google Podcasts , or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode. Newsletter & Exclusive Content: Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates. Connect with Bruce & the Community: LinkedIn: Bruce Eckfeldt Instagram: @bruce_eckfeldt Email: podcast@eckfeldt.com bruce@eckfeldt.com…

From Angel To Exit

1
Welcome to From Angel to Exit 6:08

8 weeks ago6:08