Building a Dealmaker Community: Lessons from Leading the EO Deal Exchange Conference

Last month, I had the honor of chairing the EO Deal Exchange Conference for the second consecutive year. This gathering brought together entrepreneurs from around the world, all focused on one mission: learning how to grow their businesses through strategic deals.

The conference reviews were phenomenal. But what struck me most wasn't just the stellar feedback from participants. It was watching hundreds of entrepreneurs discover what's possible when you combine authentic sharing, expert guidance, and a community that truly gets the challenges of dealmaking. Walking away from those few intense days in Los Angeles, I found myself reflecting on lessons that extend far beyond any single conference room.

The Wisdom Already in the Room

We opened the conference with deal speed networking sessions. Based on overwhelming feedback from the previous year, we actually added a second session because participants couldn't get enough.

The format is straightforward but powerful. Someone presents their deal need in a couple of minutes. Maybe they're looking to buy companies in a specific sector. Perhaps they need joint venture partners in a particular jurisdiction or industry. They could be seeking capital or looking to make strategic investments. Then everyone else in the room contributes their wisdom, connections, and ideas.

EO members are remarkably well connected. Their collective Rolodex is extraordinary. But here's what matters most: they freely share these connections and insights, even with people who might technically be competitors. There's no scarcity mentality here.

This points to something bigger than just conference programming. Whether you're organizing events or simply looking to accelerate your deal journey, there's tremendous untapped wisdom in your existing networks. You don't always need to hire the most expensive consultant or chase down the biggest names in your industry.

Within your peer groups, industry associations, and business owner communities, there are people who have walked the path you're about to walk. They've made the mistakes you're trying to avoid. They know the shortcuts you haven't discovered yet. Create spaces for that wisdom to surface. Host a small mastermind. Organize a dinner with fellow entrepreneurs. Structure conversations around real experiences with deals: how people found acquisition targets, identified key partnerships, or discovered non-traditional capital sources.

When Silicon Valley Prodigies Choose Different Paths

Our kickoff speaker was Fallon Fatemi, literally a Silicon Valley prodigy who grew up in the technology epicenter and co-founded one of the first AI-as-a-service companies with Mark Cuban. Her background reads like a tech industry highlight reel.

But the most fascinating part of our conversation came when we discussed her evolution as an entrepreneur and mother. Fallon shared something unexpected: after raising capital across multiple ventures and being immersed in the high-flying startup world, she has decided she'll never raise capital again.

This wasn't about capital raising being inherently bad. It was about recognizing what she wants at this stage of her life. With a young child and multiple businesses she still actively builds, Fallon wants control over her own destiny. She wants to create according to her own vision, without the pressures and expectations that come with outside investors.

I've talked many times on this podcast about reframing what it means to have a lifestyle business. The term gets used dismissively, as if building a business on your own terms somehow represents a lack of ambition. But lifestyle business can mean anything from bootstrapping a small service company to raising massive capital for a robotics startup because that particular grind and challenge is the lifestyle you choose.

Fallon embodied this beautifully. There was a time when her desired lifestyle involved building unicorns, partnering with celebrity investors, and chasing Silicon Valley's version of success. Now she's chosen something different, and she's done the internal work to get comfortable with that shift, even when it might not match what others expect from someone with her background.

This matters for every entrepreneur listening. Get real about what you actually want. Not what you think you should want. Not what your peers are doing. Not what some guru online says represents success. Figure out what aligns with your values, your family situation, your personal definition of freedom. Then build toward that, regardless of whether it fits conventional startup wisdom.

Angel Investing with Mentorship Built In

My longtime friend from EO New York, Daniela Landau, joined us for multiple sessions. Daniela successfully exited a health industry company several years ago and now focuses on angel investing. But she does it differently than most angel investors.

Daniela only invests in companies where she can also serve as an advisor. She doesn't want to simply write checks. She invests exclusively in ventures where she can bring additional value through her guidance and experience. This approach helps her leverage her investment while significantly improving the company's chances of success.

We brought Daniela on stage with Lauren Castle, founder of Sweet Lauren's. Sweet Lauren's is estimated to generate $120 million in revenue this year, up from $97 million last year. The company has become a leader in the healthy desserts category.

But here's the remarkable part: when Daniela and Lauren first met, Sweet Lauren's had just $83,000 in annual revenue. They met through EO's Accelerator program, which at the time had slightly more flexible entry requirements. Someone pulled strings to get Lauren in because they recognized her passion and potential.

Daniela didn't just become an investor in Lauren's company. She became her mentor. For the first few years of Sweet Lauren's existence, they met every Friday. Every single week, Daniela shared wisdom from her own entrepreneurial journey while Lauren built what would become a nine-figure business.

Their fireside chat provided a masterclass in what mentorship looks like when paired with investment and strategic support. They generously shared their journey together, the challenges of scaling from near-startup to major enterprise, and how mentorship accelerated growth while helping avoid costly mistakes.

For entrepreneurs seeking investment, think about whether you're just looking for capital or whether you want investors who bring more to the table. For those with capital to deploy, consider how your involvement beyond the check might compound your returns while creating something more meaningful than a transactional relationship.

The Power of Multiple Offers in M&A

Scott Bushke has been a DealQuest podcast guest, and he's been both a speaker and sponsor at Deal Exchange for several years. Scott runs Cornerstone, putting together 7A deals for business acquisitions. He's a great EO member and brings valuable insights year after year.

One concept Scott emphasized particularly resonated: the power of multiple offers. From the buy side, every buyer wants the same thing. They want to call you directly and say, "Hey, I want to buy your company. Let's negotiate a deal just between us." They want to avoid a competitive process because they know that process typically drives up the price.

I see this constantly in my practice. Clients get nervous. Someone has expressed interest in acquiring their business. They worry that if they run a formal process, they might lose this interested buyer. They don't want to risk the bird in hand by going back out to the market.

Here's my experience, and it aligns perfectly with what Scott discussed: in virtually every situation, legitimate buyers don't walk away when you initiate a professional process. That's a bold statement, and yes, there are occasional exceptions. Maybe you have a unique relationship with the buyer. Perhaps you've already worked together through a joint venture or strategic alliance. Maybe the fit is so specific and perfect that a broader process doesn't make sense.

But understand this: you're almost certainly leaving significant money on the table by negotiating exclusively with a single buyer. Working with a quality investment banker typically more than pays for itself through improved deal terms and higher purchase price.

Scott shared statistics demonstrating just how powerful multiple offers can be. In his experience, the original single buyer is never the ultimate buyer when he runs a formal process. Now, I've seen cases where that original buyer does win in the end, but very often they don't. Even when they do, the competitive process typically drives significantly better terms.

Running a process and getting multiple offers isn't about being greedy. It's about understanding fair market value and ensuring you're making the best decision for your business, your team, and your future. Unless there are compelling relationship or strategic reasons to negotiate exclusively, a professional process serves sellers better.

Avoiding Exit Wounds Through Inner Board Meetings

Dave Hirsch was someone I didn't know before this conference. I'm grateful we had him speak because he introduced concepts that aligned perfectly with themes I've explored on this podcast while offering new frameworks for implementation.

Dave talked about avoiding exit wounds. This refers to what many call founder depression: entrepreneurs who exit their businesses, sometimes with life-changing or generational wealth, only to lose their identity afterwards. They become lost, unmoored, sometimes clinically depressed. They achieved what they thought was the ultimate goal, only to discover the victory feels hollow.

Dave shared sobering statistics about company failures and exits. While I won't steal all his thunder since I hope to get him on the podcast soon, here's the bottom line: when you calculate the percentage of companies that actually achieve successful exits and then factor in how many of those founders are genuinely happy and satisfied afterward, you end up with roughly 13% of exiting entrepreneurs who are truly content with their outcomes.

That's a brutal number. Even if it's somewhat higher, say 30% or even 60%, there's clearly a massive satisfaction gap. Too many entrepreneurs work for decades building valuable businesses only to feel empty or regretful after selling.

Dave offers coaching and programs around this challenge, drawing on concepts from his friend Omovo, a Kyoto-based coach. The most fascinating tool Dave introduced is something called the Inner Board Meeting.

Obviously, we're all familiar with external boards made up of other people. The Inner Board Meeting is different. It's based on the recognition that we all have multiple voices, life experiences, and aspects of our personality. Some of these voices are empowering. Others are more negative or limiting. The key is bringing this internal board of directors together and ensuring any deal you pursue satisfies all these pieces of who you are.

Dave has created a physical toolkit with cards representing different internal board members. Some cards represent empowering aspects: the problem solver, the warrior, the advocate, the celebrator, the connector, the experimenter. Others represent more challenging aspects: the anxious one, the imposter, the perfectionist, the controller.

There are also situational cards for when you're stuck in your head, when everything feels urgent, when money decisions feel heavy, when you need to ask for help but it makes you feel exposed.

The process involves identifying which cards resonate with you from each category, then narrowing down to your core inner board members. From there, you examine whether a potential deal actually satisfies all these aspects of yourself. If your "warrior" is excited about the challenge but your "connector" knows the deal will isolate you from your community, you've identified a real conflict that needs resolution before signing.

This framework provides a structured way to do the internal work I always encourage clients to complete before pursuing major deals. Understanding your "why" matters tremendously. Making sure deals align with your values, your vision for life post-transaction, and all the complex pieces of your identity helps avoid becoming part of that unfortunate 13% who achieve the exit but lose themselves.

Hollywood Dealmaking Lessons

We held the conference in Los Angeles, and I realized we needed to bring the quintessential LA experience to our learning program. How could we run a deals conference in Los Angeles without featuring an entertainment industry dealmaker?

Thanks to my friend Josh Levine, who called in a favor since we had zero budget for this speaker, we secured Jeff Collins. Jeff runs a production company and is best known for Dance Moms, the long-running unscripted show that has spawned versions around the world and maintained staying power far beyond typical reality television.

Jeff shared insights about the Hollywood deal landscape, creating key partnerships, and getting shows financed. Despite everything you hear about Hollywood and the stereotypes that exist in the industry, the best deals still get done based on relationships. That's true in entertainment just as it's true in every other industry.

Jeff relies heavily on authentic partnerships and maintaining integrity. His longevity in a notoriously difficult industry comes from treating people right, keeping his word, and building genuine relationships rather than transactional connections. Those fundamentals apply whether you're producing television shows or manufacturing widgets.

The Authentic Sharing of EO Deal Talks

We started the main conference with something called an EO Deal Talk. In EO, we have what we call 5% shares or 1% shares. These are the stories we normally don't tell anyone, certainly not in business contexts. They're often emotional, deeply personal, vulnerable.

This authentic sharing provides tremendous value. When someone has the courage to share the parts of their story they usually hide, it gives others permission to acknowledge their own hidden struggles and challenges.

Lindsey opened our conference with an EO Deal Talk. She was nervous beforehand. But she absolutely crushed it, setting a tone of authenticity and vulnerability that carried through the entire event. Starting with that level of realness rather than polished keynote speeches sent a powerful message about what the conference would be.

Angel Shark Tank: Where Real Investments Happen

One popular conference element is our Angel Shark panel, which Daniela Landau headed up. Lauren Castle also participated, along with phenomenal angel investors Naz Amiri and Tanya Yuki, whom I met for the first time at this event.

Five companies pitched to the panel. Three received investment offers on stage. Obviously, due diligence and final terms get negotiated afterward, similar to how deals on Shark Tank or The Pitch podcast work. But these were serious commitments from serious investors to genuinely strong companies.

This panel demonstrates that Deal Exchange isn't just about learning and networking. Real capital flows. Real deals get done. Real partnerships form.

The Community Makes the Difference

I've shared this observation many times: most people outside the entrepreneurial world don't fully get what we go through. That's not criticism. They're not entrepreneurs. They work for someone else. They don't understand the ups and downs, the roller coaster, making payroll when things go badly, calculating risk levels, making significant investments, putting in long nights.

That's what I love about EO. Deal Exchange takes it further. Now we're in a room for several days with EO members who happen to be dealmakers. Even for someone like me who does deals every day and knows a lot about various deal types, I'm still learning. And if I'm learning, imagine the value for people who don't live in the deal world daily.

The connections made, experiences shared, and wisdom exchanged simply can't be replicated from a book. While I do most of my work virtually now, there's something powerful about being physically present with a group of people in that environment. The real magic happens at breaks, lunches, breakfasts, and dinners where conversations continue and deepen.

Investment happens. Deals get done. Joint ventures form. Acquisitions occur. And that's just from people in the room, not even counting the knowledge and connections from speakers.

Why Peer Communities Matter for Dealmakers

You don't have to join EO specifically, although I certainly recommend it if you qualify. If you're not yet at the million-plus in annual revenue that most chapters require, there's Accelerator for companies between $250,000 and $1 million.

But even if EO isn't the right fit, think about how you can create or join communities focused on dealmaking within your existing networks. Your industry groups. Your local business owner associations. Just organize a small mastermind or host a dinner.

There's wisdom in those rooms. Have people share experiences about growing businesses through deals. Ask about finding key partnerships, identifying acquisition targets, discovering non-traditional capital sources. The collective knowledge will surprise you.

Anything you want to achieve, surround yourself with people who have already achieved it or are actively pursuing it. If dealmaking is your goal, get yourself into communities of dealmakers. Learn from them. Contribute to them. That creates opportunities you simply can't access any other way.

Looking Forward

My partner Brian Mingan has taken over as EO Deal Exchange community lead. His term covers the next two years. The firm will continue our involvement, though Brian jokingly makes clear that my "retirement" from the role isn't happening. I'll still be involved.

We're already expanding internationally. We're bringing Deal Exchange to Dubai in December, creating a Deal Exchange experience as part of an existing regional EO conference. We have interest from Cape Town, South Africa for an international event next year. Other regions in Asia and Europe are expressing interest as well.

For me personally, being able to combine my passion for deals with an organization I care deeply about, one that has given me tremendous value, while creating spaces where I can provide value through my expertise, has been an honor and a blessing. That will continue in new forms.

I've tried to share some of the key lessons from the conference, even though you couldn't be there to experience it directly. My hope is that these insights resonate and make a real difference in your own dealmaking journey.

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Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.

Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!