My Serial Entrepreneurship Journey (And How to Become One Yourself)

My Serial Entrepreneurship Journey (And How to Become One Yourself) - Nathan Hirsch

My Serial Entrepreneurship Journey (And How to Become One Yourself)

A mug on a desk that says "Hustle".

My serial entrepreneurship journey has taught me a lot of lessons. This post tells the story of how it all began. I also share the key moments that shaped my journey.

I’m sharing my experience here so you can use some of these solid tips on your own journey.

The Early Days: A Dorm Room and a Big Idea

Reselling Textbooks

One day in 2009, I was sitting in my Quinnipiac college dorm room. The school bookstore charged so much money for textbooks, and I felt ripped off. There was no reason to ask students to pay so much for books they would read once. 

To make things better, I created a competing textbook business. I would buy used books from students and resell them at reasonable prices. The college got wind of it and sent me a cease and desist letter within 6 months. 

I could have just given up right there. But I saw it as the best thing that ever happened to me. 

My New Amazon Store

I had to move my business to Amazon, and soon learned that I needed to find other products to sell. My new Amazon selling account really started to take off when I found a great toy and baby niche. 

This is when I met my long-time business partner, Connor Gillivan. We were taking a Business Law class together, and decided to team up on the Amazon business. Connor and I ended up selling more than $25 million on Amazon over the next 5 years.

Discovering the Power of Virtual Assistants

A woman at a table typing on a laptop with a notebook, glasses, a smartphone, and pencils next to it.

For us, serial entrepreneurship would not have been possible without virtual assistants. But we didn’t know that at the beginning. It was a tough road.

We hired, at first, out of the same college we attended. That came with a lot of challenges. Most of the students we hired were unreliable. 

I want to make entrepreneurship simpler for millions who are just getting started. So I suggest making virtual assistants part of your plan from the very beginning.

Learning to Outsource

After one of my friends introduced us to virtual assistants, we went on a learning journey. We wanted to know how to make the best hires. Then, we got our Amazon store running successfully with virtual assistants. That changed our lives forever.

We decided to share our success by building a freelance marketplace called FreeUp. There, other entrepreneurs who struggled to hire could find pre-vetted virtual assistants for their needs. We put in $5,000 and scaled it to $12 million in yearly revenue by year 4. In 2019, we sold FreeUp to The HOTH.

Teaching to Outsource, and More

We learned so much more building the FreeUp Marketplace. We wanted to take everything we learned and help entrepreneurs. So, we built B2B businesses covering hiring, bookkeeping, and SEO. 

With our businesses, we offer other entrepreneurs the exact same process we used to build our own success. Outsource School, EcomBalance, AccountsBalance, TrioSEO, and The Savvy SEO are part of our current portfolio.

Scaling Businesses with Innovative Solutions

Building FreeUp

FreeUp will always be one of my favorite serial entrepreneurship stories. It begins with a pain point that was frustrating us. We started hiring virtual assistants, which was great. But hiring online from platforms like Odesk (now Upwork), Upwork, and Fiverr was hit and miss. 

We spent years trying to find the best freelance talent for our Amazon business. It took so much time, and we still had too much turnover. We needed a better way.

I always suggest building a business based off a problem that many people in a specific market have. When we discovered that hundreds of other people shared our hiring challenges, we created a service that targeted them.

We launched and grew FreeUp with a loyal following of clients from our eCommerce business offerings – consulting and selling on Amazon. Helping them to hire reliable freelancers became the most popular service. 

The unique value proposition of offering pre-vetted freelancers formed the foundation for a strong business.

Selling FreeUp

The HOTH acquired FreeUp in 2019. We weren’t looking to sell originally, but when the HOTH approached us, we realized it was best. They had the advanced experience to scale FreeUp past $20 million or even $50 million per year. 

We put a lot into building FreeUp to where it was and we loved everyone that was a part of the marketplace. Letting go was best for the company, so we could see it hit record growth in the years to come. 

A man with a tablet computer and tools looking at design schematics.

Lessons Learned

The pros and cons of entrepreneurship can threaten to take anyone on a rollercoaster ride. The serial entrepreneurship experience itself has been the most valuable lesson for me. My goal, though, is to help you so you don’t have to go through the same pitfalls. 

Here are my favorite key strategies and insights from my experience scaling and exiting FreeUp.

Timing the Market

Both building and selling FreeUp depended on perfect timing. We were able to see the need for ecommerce virtual assistants. Then we shifted as the market called for help in various industries, like real estate and marketing agencies.

The acquisition of FreeUp was completely strategic. The market was getting more and more competitive, and the economy was at an all-time high. We exited at a time that opened opportunities for us to explore new ventures.

Document the Journey

I owe a lot of my success as an entrepreneur to how I kept records of every decision made. Documenting the journey give you the roadmap you need to evaluate each step. This is how I saw what I missed and what worked. 

I suggest that you take notes on everything, no matter how insignificant it might look. You never know what can end up being a significant factor. When you get to see how one thing led to another, you will learn how to make better decisions next time. 

Rinse and Repeat

I took a very strategic approach to building a portfolio of businesses after the FreeUp sale. The first step there was finding reliable people to operate each venture. This way, I could step out of a lot of the day-to-day and focus on high-level strategy and growth.

I suggest choosing niches that target important pain points, but that other providers tend to overlook. For us, these included hiring, financial management, and SEO. They might look unglamorous, but these critical areas gave us stable and scalable businesses.

When launching new businesses, I prefer to start quickly. I aim to put out a minimal viable product, even if it’s just in the beta phase. Then, I make improvements quickly based on feedback. 

With some initial sales, I can shift my focus to building strong processes and scaling the business sustainably. This is the system that has built our current portfolio.

Building a Portfolio of B2B Services

A man on a sofa reading a book below a sign that says, "Proof".

Solutions to Common Serial Entrepreneurship Challenges

Each business that we currently run, like FreeUp, we built around solving a problem. This is central to my serial entrepreneurship success. Here’s how each company in our portfolio helps with common challenges for serial entrepreneurs.

Outsource School

Outsource School was born immediately following the FreeUp acquisition in 2019. We wanted to help millions of others to unlock the potential of virtual assistants. 

We know how well our system works to help accelerate business growth. It’s the same one we used to bootstrap FreeUp from the ground up to 8 figures with 40+ virtual assistants.


Connor and I founded EcomBalance in 2021 after we discovered a gap in bookkeeping services. Ecommerce businesses needed simple bookkeeping services that understood their needs. 

EcomBalance is part of their mission to change the way businesses offer bookkeeping to eCommerce companies.


AccountsBalance is an EcomBalance sister company. The idea behind it is the same, offering a solution to the need for reliable bookkeeping services for online companies. AccountsBalance is the other part of their mission to change the way bookkeeping is offered. This time, the focus is on agencies, software companies, and other online companies.


Connor and I have built and scaled multiple businesses. SEO was pivotal in each one, from 6, 7, and up to 8 figures. With Steven Schneider as CEO of TrioSEO, our mission is to help other entrepreneurs establish this as the cornerstone of their business. We again offer the exact strategies that worked for us.

The Savvy SEO

The Savvy SEO mission is to empower clients to use the internet to its full potential. We offer effective solutions, including custom website design and marketing. We want the best for our clients, and know that quality can be affordable. 

Most business owners don’t have internet expertise, and suffer for it. Even the smartest serial entrepreneurs can’t reach their full potential without the unique combination of creativity, innovation, and expertise that will drive their digital success. 

Final Thoughts

I wouldn’t trade my serial entrepreneurship journey for anything. But I also understand the value of not having to reinvent the wheel. This is why I put these snippets here for you, and I hope they can springboard you on your own journey.

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Nathan Hirsch

On a mission to make entrepreneurship simpler for millions.

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