Case Study

How The Flyover Maxed Their $5M Reg CF

A fast-growing new media company turned its loyal readership into 3,708 investor-owners, maxing out the Reg CF cap and oversubscribing by nearly $100K, proving that audience trust is the ultimate capital strategy.

$5M+

Raised (Reg CF Max)

3,708

Retail Investors

~6 Months

To Full Subscription

$1,365

Average Investment

4M+

Daily Readers

~$100K

Oversubscribed

When Guy Short launched The Flyover in February 2023, he had a clear-eyed mission: deliver fact-first, no-spin news to the millions of Americans tired of media bias. Within two years, the newsletter had exploded to over 2.5 million daily readers, achieved profitability, and built one of the most engaged audiences in digital media.

But here is the twist: instead of chasing traditional venture capital to fuel the next phase of growth, Short made a bet on the people who already believed in The Flyover. He opened the cap table to his own readers.

The result? The Flyover maxed out the full $5M Reg CF cap from 3,708 investors in roughly six months, hitting its target almost to the day. Demand was so strong that the raise oversubscribed by nearly $100K, and hundreds of would-be investors had to be turned away.

The Mission: Readers First, Always

The Flyover was built on a simple premise: Americans deserve news they can trust, delivered without spin or agenda. That philosophy attracted millions of daily readers and created something rare in media, a genuine community of trust.

Opening the cap table to that community was a natural extension of the same principle. If The Flyover belongs to its readers in spirit, why not in equity too?

                Living their values: A media company built on reader trust gave readers the chance to become owners
Community alignment: Virtually all 3,708 investors were existing Flyover readers before they invested
Incredibly low cost of capital: Trust-based distribution eliminated the need for expensive investor acquisition
Strategic growth fuel: Capital deployed directly into audience growth, product expansion, and new formats
Oversubscribed demand: Had to turn away hundreds of would-be investors after maxing the $5M cap

            

From Newsletter to New Media Powerhouse: The Flyover's Growth Story

Feb 2023

The Launch

Guy Short and Jacob Leis launch The Flyover with a mission to cut through media noise and deliver bias-free news directly to readers. The team focuses relentlessly on product, trust, consistency, and execution.

2024

Explosive Growth

Explosive Growth & Profitability

~7x Revenue Increase

The Flyover hits profitability within its first two years, a rare feat in digital media. Monthly revenue surges from $63K in February 2024 to $423K by February 2025, a nearly 7x increase. New state editions launch across Florida, Ohio, Texas, and more.

Mid-2025

Opening to Investors

$5M Target

$35M Pre-Money Valuation

The Flyover partners with DealMaker to launch a Reg CF offering at a $35M pre-money valuation, priced at $2 per share with a $750 minimum investment. The raise targets the maximum $5M cap.

Jan 2026

Maxed Out

$5M+ Raised

3,708 Investors

4M+ Daily Readers

The Flyover successfully completes its $5M Reg CF raise from 3,708 investors in approximately six months, hitting the target almost to the day. The campaign oversubscribes by nearly $100K, and hundreds of additional investors have to be turned away. The company simultaneously crosses 4 million daily readers.

A New Media Company, Not a Newsletter Company

Guy Short is clear about the distinction: The Flyover is not a newsletter company. It is a new media company focused on building large, durable audiences across different formats and platforms.

The numbers back it up:

                4 million+ daily readers crossed in January 2026, achieved in under three years
1 million+ monthly podcast views/listens on YouTube, launched from scratch in 2025
100% direct-sold ad fill rate across the podcast, a brand-new audience they own and monetize
Open rates soared from mid-50s to mid-70s between January 2024 and January 2026
Record revenue in 2025 with consistent month-over-month growth and strong year-over-year increases
24% net income margin with a $6M+ annual revenue run rate
Multiple state editions covering Florida, Ohio, Texas, and more, with national and local coverage

            

In a media landscape where most startups never reach profitability and legacy outlets face declining trust, The Flyover built a sustainable, diversified business by focusing on what readers actually want: honest news delivered without spin.

"What mattered most to me wasn't just the capital, it was who it came from and what it cost. Virtually all our investors were Flyover readers long before they invested. That led to an incredibly low cost of capital, and a strong signal of trust."

Guy Short, Founder, The Flyover

Powered by DealMaker

The Flyover selected DealMaker to facilitate its Reg CF offering because of DealMaker's proven track record with high-profile raises and its ability to deliver a seamless, self-hosted experience that maintained The Flyover's brand throughout the investor journey.

Why The Flyover Chose DealMaker

                    Self-hosted solution keeping The Flyover's brand front and center throughout the entire investment process
Seamless investor onboarding for both accredited and non-accredited investors, with a low $750 minimum
Real-time analytics to track and optimize the raise as it progressed
Compliance expertise ensuring full SEC regulatory compliance throughout the campaign
Marketing services support through DealMaker's integrated marketing engine, driving investor engagement and conversion

                

The partnership between The Flyover and DealMaker demonstrated the power of combining a deeply trusted brand with world-class capital raising infrastructure. With an average investment of $1,365 from readers who already believed in the mission, The Flyover achieved one of the most efficient Reg CF raises in the industry.

What Comes Next

Virtually all of the Reg CF capital is being deployed directly into growth. The Flyover has identified four key areas of investment:

                Audience Scaling: Expanding readership toward 5 million+ daily readers through new state editions and subscriber growth
Product & Distribution: Scaling the podcast, launching a text messaging channel, and enhancing content personalization
Data & Technology: Advanced analytics, personalization engines, and deliverability improvements that have already pushed open rates into the mid-70s
Talent Acquisition: Hiring experienced editorial and growth talent to maintain quality while scaling operations

            

DealMaker was thrilled to play a role in this campaign, ultimately driving impact across four dimensions:

                For The Flyover: Building a community of 3,708 investor-owners who already trusted the brand and will champion its growth
For Investors: Access to equity in one of the fastest-growing media companies in America, built on a profitable, sustainable model
For the Industry: Proving that audience trust is the most powerful capital-raising asset a media company can build
For the Future: Setting the standard for how new media companies can use community capital to grow on their own terms

            

Quotes

"DealMaker made it straightforward to run a $5M raise from the people who already knew us best, our readers. Their self-hosted solution kept The Flyover's brand front and center, and the compliance and onboarding experience was seamless. We targeted a six-month raise, and we hit it almost to the day. That kind of execution matters when you're building something with this much momentum."

Guy Short, Founder, The Flyover

"The Flyover was built by its readers long before they became investors. Their trust, their feedback, their daily engagement, that is what built this company. Giving them the chance to own a piece of it was never just a fundraising strategy. It was the right thing to do. DealMaker understood that from day one, and they built an experience that honored that relationship."

Guy Short, Founder, The Flyover

Strategic Value of Reader-Investors

"What mattered most was not just the capital, it was who it came from and what it cost. Virtually all our investors were Flyover readers long before they invested. That led to an incredibly low cost of capital, and a strong signal of trust. These 3,708 investors are not just shareholders. They are our most engaged advocates, and they are the foundation for everything we build next."

Guy Short, Founder, The Flyover

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