The $100 Bill Pitch: How We Got Jayson Myers' Attention and Asked for $1 Million

This is the complete, unfiltered story of our first real investor conversation with Jayson Myers (also known as M. Jayson Meyer), the CEO and founder of Synergy Billing, a leading healthcare revenue cycle management company headquartered at Fountainhead in Holly Hill, Volusia County, Florida. It's a story about nerves, bold asks, creative pitches, and the reality that sometimes "yes" doesn't mean yes. This is the story of how we met Jayson Myers (also known as M. Jayson Meyer), CEO of Synergy Billing at the Fountainhead headquarters, asked him for $1 million, and what happened next.

The Setup: Meeting Jim Cameron at Synergy Billing's Fountainhead Headquarters

In our very early days of seeking BC and investor funding for InvestlerRealty (one of the portfolio companies that would later become part of Investler Solutions), I was reached out to by Jim Cameron (LinkedIn), a lobbyist and business advisor I had known for quite some time. Jim Cameron, founder of Jim Cameron Consulting, wanted to catch up over coffee and talk about some new developments that were happening in the city.

We met at Fountainhead, Synergy Billing's headquarters located at 1200 Synergy Way, Holly Hill, Florida 32117 in Volusia County. Fountainhead is a beautiful headquarters, a previously converted school building that now houses one of the most successful healthcare revenue cycle management companies in the region. Synergy Billing LLC operates from this Fountainhead location, providing healthcare revenue cycle management services and billing solutions to healthcare providers across the United States.

Walking into Fountainhead was an experience I'll never forget. What was once a massive gym was now filled with hundreds of cubicles, a sea of workspace that stretched out before me. But here's the thing: out of all those cubicles, maybe only three people were actually working in them. The space was massive, almost overwhelming, and I immediately envisioned my company being in a place like this one day.

Then I saw Jayson's office. It was like something out of The Wolf of Wall Street, a loft up top with the center being just the office, surrounded by transparent glass. Inside was a 20-foot conference table with chairs wrapped around it, the focal point of all meetings. When you walked out from that office, you looked over all the cubicles below. It was a room that commanded presence. And that pretty much gave me the jitters right there.

I was immediately infatuated by the space and the company. Synergy Billing is a healthcare revenue cycle management company providing billing and practice management solutions, and their headquarters at Fountainhead represents the kind of success we're building toward.

Jim Cameron introduced me to Jayson Myers (LinkedIn), the CEO of Synergy Billing and owner of Fountainhead.

At that time, I was already creating my pitch deck for InvestlerRealty, so I took the opportunity to speak with Jim Cameron about what I was building. He said that he wanted to get me in touch with Jayson Myers, he thought Jayson would be interested in what I'm building.

The Creative Pitch: The $100 Bill Strategy

Before meeting Jayson Myers directly, I gave Jim Cameron a printed pitch deck with a $100 bill sticking out of it. On the $100 bill, I wrote something along the lines of "See inside" or similar. Basically, the whole goal was just to get Jayson Myers to read the pitch deck because I knew once he read the pitch deck, it would 100% grab his attention and would captivate him to want to learn more about what we're building.

This wasn't about the money, it was about getting attention. In a world where investors receive hundreds of pitch decks, you need to stand out. The $100 bill was a creative way to ensure Jayson Myers would actually open and read our pitch deck about InvestlerRealty, our virtual real estate brokerage.

And that's exactly what happened.

The Call: Getting Jayson Myers' Attention

I ended up getting a call from Jayson Myers. We exchanged emails and scheduled a time to meet in person. When we scheduled that meeting, I was beyond nervous. I was nervous due to the fact that I cared so much about the company, and this was really the first time we had initially spoken with investors.

Thankfully for Shelly, my COO, who led the initial conversations about the investment. I had no idea what I was doing, definitely a learning curve. That was the first time we ever talked to an investor, and Jayson Myers, CEO of Synergy Billing, was our first real investor conversation.

The Meeting: Asking Jayson Myers for $1 Million

Walking into that office, looking out over all those cubicles from that commanding space, I felt like everything was relying on this moment. The reality was, that wasn't the case, it was more just myself getting to myself in that situation. But I believed so much in the company (and I still do) that it felt like the weight of the world was on my shoulders.

I had done telemarketing before, where I was pretty comfortable asking people for their money over the phone and processing credit cards. But asking somebody in person for a substantial number? That's something completely different. The jitters were real.

When we met in person, Jayson Myers asked how much I wanted. I said $1 million.

Kudos to me for asking, for having the balls to ask. Not everybody would ask somebody they just met for the second time for a $1 million investment. But here's the thing: asking for such a substantial number wasn't just about the money itself. It was about getting those pre-meeting jitters out of the way. It was about raising my threshold for the amount of asking that I could do. If I could ask for $1 million, then asking others for $500,000 or $200,000 would feel more comfortable. It was more of a test and a true testament to myself to see if I had the capability to ask somebody for this type of money and try to back it up, rather than the actual amount itself.

Jayson Myers shook my hand and said that he would be willing to invest. The boldness paid off, at least in terms of getting a commitment.

The Presentation: A Pre-Recorded Four-Minute Pitch

I had a four-minute presentation that I pre-recorded so I didn't have to have all the jitters while trying to present it in person. At the time, this wasn't about our entire ecosystem, it was specifically focused on InvestlerRealty.com, our virtual real estate brokerage.

The presentation was essentially a demonstration of the platform itself. I had prepared a bunch of documents, what I'm calling "fluff documents" now, but they weren't really fluff. They were just numbers. A lot of numbers. But looking back, they lacked the depth and detail that would have made them truly compelling.

Here's the thing: I felt like I was overprepared. I had documents as if I was already an executive CEO running a multi-million dollar company. I was so prepared that I think that was another downfall, there was so much stuff that I wanted to get out that it really probably was the downfall of that pitch to Jayson in his office. I had everything ready, but maybe too much. Sometimes less is more.

Pre-recording the presentation was a smart move, it allowed me to focus on the conversation rather than worrying about presenting while nervous. But the content itself? That's where I made mistakes I didn't realize at the time. And the overpreparation? That might have been a mistake too.

The Commitment: Jayson Myers' Handshake

Jayson Myers shook my hand and said that he would be willing to invest. This was a huge moment for us. Our first investor conversation, and we got a commitment from Jayson Myers, CEO of Synergy Billing, a successful healthcare revenue cycle management company.

The handshake felt real. The commitment felt real. We left that meeting thinking we had our first investor.

The Aftermath: Volusia County Business Events and New Connections

No hate to Jayson Myers or anything, great guy, very successful founder. I even had the opportunity to attend some pretty cool Volusia County business events with him, where I got to meet Daryl Scott, a very successful entrepreneur who built Venus Swimwear into a $100 million international brand. I recently attended another incredible Volusia County Economic Development event focused on funding readiness and entrepreneurship, where I got to hear Daryl's keynote.

Daryl's story was incredibly inspiring. We're connected on LinkedIn and Facebook, and these Volusia County business events have been valuable networking opportunities. The Florida business community, especially in Volusia County, is tight-knit, and these events provide valuable insights into how successful founders operate.

Who knows, maybe we'll pitch Daryl Scott next. Daryl, if you're reading this, let's talk.

The Reality: When "Yes" Becomes Silence

But here's the thing: Jayson Myers said he would invest. He shook my hand and committed. But then... nothing. No follow-through. No investment. Just silence.

We sent follow-up emails. We tried to reconnect. But Jayson Myers, CEO of Synergy Billing, didn't follow through on his commitment to invest in InvestlerRealty.

This was our first real investor conversation, and it taught us a valuable lesson: sometimes "yes" doesn't mean yes. Sometimes a handshake and a commitment don't translate to actual investment. Sometimes you do everything right, you make the connection through Jim Cameron, you deliver the creative pitch with the $100 bill, you get the commitment from Jayson Myers, and still, nothing happens.

Lessons Learned: What This Taught Us About Investor Conversations

This experience with Jayson Myers and Synergy Billing taught us several important lessons:

Lesson 1: Creative Pitches Work

The $100 bill strategy worked. It got Jayson Myers' attention. It got him to read our pitch deck. It got us the meeting. Creative approaches to investor outreach can break through the noise.

Lesson 2: Bold Asks Are Necessary

Asking for $1 million in our second meeting was bold, but necessary. You have to ask for what you need. Not everyone will say yes, but you'll never get it if you don't ask.

Lesson 3: Commitments Aren't Investments

A handshake and a verbal commitment from Jayson Myers didn't translate to actual investment. Until money is in the bank, it's not real. This is a hard lesson, but an important one.

Lesson 3.5: Detailed Use of Funds Matters

We thought we had a good use of funds guide. We didn't. When you ask for money, you need specific line items, exact amounts, exact purposes, expected returns. Not "money for marketing" but "$1,668 for DigiCert VMC certificate to improve email deliverability and brand recognition." Investors want to see you've thought through every dollar. We learned this the hard way.

Lesson 4: Every Conversation is Valuable

Even though Jayson Myers didn't follow through, the experience was valuable. We learned how to pitch. We learned how to ask for investment. We met other entrepreneurs like Daryl Scott. We attended Volusia County business events, including a recent Volusia County Economic Development event focused on funding readiness. Every investor conversation teaches you something, even the ones that don't result in investment.

Lesson 5: Build Regardless

We're building regardless. Every conversation is a learning experience. Every "yes" that becomes silence is data. And we're still here, still building, still moving forward.

About Jayson Myers, Synergy Billing, and Fountainhead

Jayson Myers (also known as M. Jayson Meyer or M. Jayson Meyer, LinkedIn) is the CEO and founder of Synergy Billing (also known as Synergy Billing LLC), a leading healthcare revenue cycle management company headquartered at Fountainhead located at 1200 Synergy Way, Holly Hill, Florida 32117 in Volusia County, Florida. Fountainhead is a beautifully converted former school building that serves as Synergy Billing's headquarters.

Synergy Billing operates in the healthcare technology space, providing comprehensive revenue cycle management services, billing solutions, and practice management services to healthcare providers, FQHCs (Federally Qualified Health Centers), and healthcare organizations across the United States. Jayson Myers has built Synergy Billing into one of the most successful healthcare revenue cycle management companies in the region, with Fountainhead serving as both the company headquarters and a symbol of the success Jayson Myers has achieved in the healthcare billing industry.

Synergy Billing's Fountainhead headquarters represents the kind of success we're building toward, a vertically integrated company that combines deep operational knowledge with technology innovation. Jayson Myers and Synergy Billing have established themselves as leaders in healthcare revenue cycle management, helping healthcare providers optimize their billing processes and improve revenue collection.

About Jim Cameron and Jim Cameron Consulting

Jim Cameron (LinkedIn) is a lobbyist, business advisor, and founder of Jim Cameron Consulting, based in Volusia County, Florida. Jim Cameron facilitated the introduction between InvestlerRealty and Jayson Myers at Synergy Billing's Fountainhead headquarters. Jim Cameron's role as a connector in the Volusia County business community highlights the importance of local networks and relationships in fundraising and business development. Jim Cameron Consulting serves as a bridge between entrepreneurs, investors, and business leaders in the Volusia County and Central Florida region.

Daryl Scott is the founder of Venus Swimwear, a $100 million international brand. We met Daryl through Volusia County business events, and his story of building Venus from a startup to a massive success was incredibly inspiring. We're connected on LinkedIn and Facebook.

Volusia County, Florida has a vibrant, tight-knit business community. Volusia County is located in Central Florida and includes cities like Holly Hill, Daytona Beach, Ormond Beach, and DeLand. Through our interactions in Volusia County, we've attended multiple business events and met successful entrepreneurs. The Volusia County business ecosystem is supportive and interconnected, with successful founders like Jayson Myers of Synergy Billing helping other entrepreneurs. Fountainhead, located in Holly Hill, Volusia County, serves as a hub for business activity in the region.

Why $1 Million and Why Jayson Myers Made Sense

At the time, we were seeking funding for InvestlerRealty, our virtual real estate brokerage. The $1 million ask wasn't arbitrary, it was what we needed to scale the brokerage operations, build out our technology infrastructure, and expand our platform.

But it was also necessary to get those pre-meeting jitters out of the way. I had experience asking people for money over the phone in telemarketing, but asking somebody in person for a substantial number is completely different. Asking for $1 million would help me get my jitters out and essentially raise my threshold for the amount of asking that I could do. If I could ask for $1 million, then asking others for $500,000 or $200,000 would feel more comfortable. It was more of a test and a true testament to myself to see if I had the capability to ask somebody for this type of money and try to back it up, rather than the actual amount itself.

The connection with Jayson Myers made sense. As CEO of Synergy Billing, he understood vertical integration, combining deep operational knowledge with technology. Similarly, InvestlerRealty (which is now part of Investler Solutions, our parent company and vertically integrated real estate technology ecosystem) combines real estate operations with technology innovation. Both require understanding operations and technology.

Note: Today, Investler Solutions is the parent company (holding company) operating three portfolio businesses: Investler.com, InvestlerRealty.com, and Brokurz.com. But at the time of this pitch, we were specifically seeking funding for InvestlerRealty.

The Reflection: What We'd Do Differently

Looking back on our experience with Jayson Myers and Synergy Billing, there are things we'd do differently:

1. Get it in writing - A handshake isn't enough. Get commitments in writing.
2. Set clear timelines - Establish when the investment would happen.
3. Follow up more aggressively - We could have been more persistent in follow-up.
4. Build relationships first - Spend more time building the relationship before asking for investment.
5. Create a detailed use of funds guide - This is a big one, and I need to be honest about it.

The Use of Funds Mistake: What I Learned

One of the biggest things I learned from this experience is that when you ask for money, you need to have a detailed plan of what you're going to utilize the money on. And even though we had what we thought was a good use of funds guide, it wasn't a real use of funds guide.

I was saying things like "X, Y, Z on marketing" or "we need money for operations" but that's not enough. Instead, I should have had direct, specific items that needed to be purchased, with exact amounts, reasons, and expected returns.

Here's what a proper use of funds would look like:

For example, instead of saying "we need money for marketing," it should be:

DigiCert Verified Mark Certificate (VMC) / Blue Authenticated Trademark Certificate

• Amount: $1,668
• Purpose: Email deliverability and brand recognition
• Implementation: Combine with email authentication standards (BIMI and DMARC)
• Expected Outcome:
  • Instant visual cue for recipients that our email is authentic
  • Blue authenticated checkmark in Gmail
  • Stop emails from hitting spam folders
  • Increase deliverability to agents
  • Create brand trustworthiness
• Return: Improved agent communication, reduced missed opportunities, enhanced professional image

This is specific. This is actionable. This shows you've thought through exactly what you need and why.

We were asking for $1 million, but we should have broken it down line by line:

• $1,668 for DigiCert VMC certificate
• $X for specific software licenses
• $Y for specific marketing campaigns with expected ROI
• $Z for specific hires with defined roles

Every dollar should have a purpose, a reason, and an expected return. That's what investors want to see. That's what we didn't have.

But we're learning. Every investor conversation teaches us something. Every "yes" that becomes silence is data. And this lesson about use of funds? It's one I'll never forget.

The Current Status: Building Regardless

We're building regardless of who believes in us today. We're still here. We're still building. We're still growing.

Investler Solutions continues to operate three portfolio companies. We have 100+ active agents. We're building a vertically integrated real estate technology ecosystem.

The best revenge is massive success.

Conclusion: The Jayson Myers Story

This is the story of our first investor conversation with Jayson Myers, CEO of Synergy Billing. It's a story about creative pitches (the $100 bill), bold asks ($1 million), and the reality that sometimes commitments don't materialize.

But it's also a story about learning, growth, and building regardless. We met Jayson Myers through Jim Cameron at Synergy Billing's Fountainhead headquarters in Volusia County, Florida. We got a handshake commitment. We didn't get the investment.

But we're still building. And that's what matters.

If you're a founder reading this, know that investor conversations don't always work out. That's okay. Keep building. Keep asking. Keep learning. Every conversation is valuable, even when it doesn't result in investment.

This is our story. This is radical transparency. This is how we're building Investler Solutions.

Who knows, maybe we'll pitch Daryl Scott next. Daryl, if you're reading this, let's talk.

Frequently Asked Questions About Jayson Myers, Synergy Billing, and Fountainhead

Who is Jayson Myers?

Jayson Myers (also known as M. Jayson Meyer or M. Jayson Meyer) is the CEO and founder of Synergy Billing, a leading healthcare revenue cycle management company based in Volusia County, Florida. Jayson Myers operates Synergy Billing from the Fountainhead headquarters located at 1200 Synergy Way, Holly Hill, Florida 32117.

What is Synergy Billing?

Synergy Billing (also known as Synergy Billing LLC) is a healthcare revenue cycle management company that provides billing services, revenue cycle management, and practice management solutions to healthcare providers, FQHCs, and healthcare organizations. Synergy Billing is headquartered at Fountainhead in Holly Hill, Volusia County, Florida.

Where is Synergy Billing located?

Synergy Billing is headquartered at Fountainhead, located at 1200 Synergy Way, Holly Hill, Florida 32117 in Volusia County, Florida. Fountainhead is a converted former school building that serves as Synergy Billing's corporate headquarters.

What is Fountainhead?

Fountainhead is the headquarters of Synergy Billing, located at 1200 Synergy Way, Holly Hill, Florida 32117 in Volusia County, Florida. Fountainhead is a beautifully converted former school building that houses Synergy Billing's operations. Jayson Myers owns Fountainhead, which serves as both the corporate headquarters and a symbol of Synergy Billing's success in healthcare revenue cycle management.

Who is Jim Cameron?

Jim Cameron is a lobbyist, business advisor, and founder of Jim Cameron Consulting, based in Volusia County, Florida. Jim Cameron facilitates connections between entrepreneurs, investors, and business leaders in the Volusia County and Central Florida business community.

How do I contact Jayson Myers or Synergy Billing?

Synergy Billing can be contacted at their Fountainhead headquarters at 1200 Synergy Way, Holly Hill, Florida 32117. You can reach Synergy Billing by phone at 877-242-8475 or visit their website at synergybilling.com. Jayson Myers can be reached through his personal website at mjaysonmeyer.com or on LinkedIn.

What does Synergy Billing do?

Synergy Billing provides comprehensive healthcare revenue cycle management services including billing services, A/R recovery, revenue cycle assessments, co-sourcing and staff support, denial prevention, board and executive reporting, and the WorkSmart MD Platform. Synergy Billing specializes in serving FQHCs (Federally Qualified Health Centers) and healthcare providers across the United States.

Where is Fountainhead located?

Fountainhead, the headquarters of Synergy Billing, is located at 1200 Synergy Way, Holly Hill, Florida 32117 in Volusia County, Florida. Fountainhead is in the Holly Hill area of Volusia County, which is part of the Central Florida region.