Long Tail Ventures

Long Tail Ventures

We Acquire And Scale
Online Businesses

Our founders have $100M+ in online revenue, leveraging data, tech, and paid traffic to grow digital assets.
We aim to be the Warren Buffett of online businesses.

Businesses Acquired

4

Websites & Apps

> 20

Monthly Pageviews

> 4M

“Deciding to sell my business wasn’t easy. I had grown it from a side project into a thriving venture that made a meaningful impact on my family’s life. When it came time to choose a buyer, I wanted a team that would genuinely care for the company and continue its growth.

Long Tail Ventures was that team. Their approach was professional, and the closing process was smoother than I could have imagined. I’m confident I made the right choice.”

Stuart Cargill​

A Better Alternative to Private Equity

Long Tail Ventures was built on a simple belief:

Buying profitable businesses with proven product-market fit is far more efficient, and far lower risk, than starting from scratch.

We are not a typical private equity fund.

We don’t operate under fixed fund timelines, forced exits, or pressure to manufacture liquidity. That freedom allows us to make rational decisions, preserve what already works, and compound value over the long term.

We acquire businesses to operate them, not to flip them.

Why Founders Choose LTV

Selling your business is not just a financial decision.
It’s a decision about legacy, people, and what happens next.

Founders choose LTV because:

  • We buy businesses to run them long term, not strip them for short-term gains
  • We pay fair valuations based on real fundamentals
  • We respect teams, customers, and existing culture
  • We don’t force artificial growth targets or rushed exits
  • We bring operational expertise, not just capital

Many of the businesses we acquire continue operating with the same teams, leadership, and identity… just with better systems, more support, and a stronger balance sheet behind them.

If you’ve built something solid and want a thoughtful transition, we’re likely a good fit.

How We Scale What Already Works

We focus on practical execution, not financial engineering.

Across our portfolio, we apply the same core principles that have helped scale more than $100M+ in sales:

  • Proprietary technology that enables scalable growth through paid traffic
  • Data-driven decision making using the 80/20 principle
  • Pricing optimization, funnels, cross-selling, and retention
  • Team building, systems, and disciplined operations

No hype. No shortcuts. Just repeatable execution.

How Capital Partners Work With LTV

Partner With Us on Profitable Acquisitions

We already operate profitable businesses that generate cash flow.

Capital is raised selectively and primarily on a deal-by-deal basis to acquire specific companies we have already identified, diligenced, and negotiated.

Our approach is simple:
we only raise capital when there is a clear use for it.

Most of our capital today is structured as asset-backed financing, not speculative equity.

Depending on the opportunity and the partner, capital may be structured as:

  • Debt with fixed or variable returns, backed by the acquired business
  • Convertible instruments tied to the specific acquisition
  • Equity participation at the asset level
  • In rare cases, strategic equity at the LTV holding level

Every structure is designed around one principle:
protect the downside first, then participate in the upside.

Why This Model Works

We review thousands of businesses and speak to hundreds of owners before selecting a handful of opportunities each year.

Our deal flow is proprietary and relationship-driven, built over more than 15 years and 100+ online business acquisitions.

That means:

  • We buy at fair, often conservative multiples
  • The businesses are already profitable at acquisition
  • Capital is deployed into operating assets, not ideas

Because we are operators first, we structure deals the same way we would structure them with our own balance sheet.

A Long-Term Owner Mindset

We acquire businesses to operate them for the long term.

We don’t face fixed fund timelines, forced exits, or pressure from LPs to manufacture liquidity. That allows us to make rational decisions, preserve teams, and focus on durable growth.

If an exceptional exit opportunity arises, we may pursue it.
But exits are optional… not required.

Our Story

Mike started his career at JP Morgan as a Private Client Banker, working with high-net-worth clients. Year after year, he ranked among the top employees, cracking the top 250 out of 20,000 reps. His goal? Become a financial advisor. But a sudden policy change shut the door on internal promotions.

That was the wake-up call. Tired of office politics dictating his future, Mike turned to entrepreneurship. But with a mortgage, a wife, and kids in New York, he couldn’t afford to quit his job and start from scratch. A side hustle wouldn’t cut it. So, he looked into buying a business instead.

His colleagues, knowing his work ethic, believed in him. They backed his vision, and together, they bought a retail store. A few years later, they sold it for a solid gain. Along the way, Mike became a top seller on Amazon and eBay, mastering online sales. That skillset landed him in Dubai, where he helped scale a cloud kitchen business to $30M ARR before it was acquired by private equity.

For his next move, Mike looked back at what started it all—buying a business and making it better. He knew the model worked. But to scale it, he needed the right partner.

That’s when he met Dan.

Dan started coding at around 14. By 16, he was already building websites for clients and running his first business.

When he decided to move overseas, he didn’t raise money. He traded skills instead. One website paid for his airplane ticket. Another covered a four-month English course in New Zealand. From there, he kept building.

Over the next two decades, Dan launched and scaled multiple online businesses entirely bootstrapped. By 2012, he was operating a high-traffic portfolio with a 20-person team when a major shift wiped out most of it. He reduced the team to five and pivoted decisively into paid media.

He built and scaled multiple digital offers, generating millions in revenue and mastering performance marketing at scale. In 2016, he launched a tracking SaaS that failed, but it led to a more powerful model. His next ad technology venture scaled to $5.1M in a single month.

From there, Dan rebuilt the group with a different structure… multiple businesses, shared systems, and no dependence on a single platform. Today, the group operates with a team of around 70 people, powered by proprietary systems processing over a billion data points daily and that have generated nine-figure revenue.

That experience shaped his belief: execution creates value, but execution paired with aligned capital creates durability.

Built for Founders. Structured for Capital. Run by Operators.

Together, Mike and Dan founded Long Tail Ventures to create a better alternative to traditional buyers and traditional funds.

A holding company designed to:

  • give founders a thoughtful, fair exit
  • give capital partners disciplined, asset-backed opportunities
  • build and operate strong businesses for the long term

Join us on the Adventure

Part of the joy of the hunt is talking to entrepreneurs and investors on a regular basis. We’re always learning about new ideas, frameworks, and emerging trends.

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