Build Multimillion Dollar Business


This week, I had a chat with the founders of FreeeUp, Nathan Hirsch and Connor Gillivan, about their advice on building multimillion dollar online businesses. They are preparing to launch their first published book together in the next month called Secret of Strap: How to Bootstrap Million Dollar Companies and I wanted to learn more about their advice.

The following is a back and forth where they share their best practices, sneak peaks into their book, and their outlook for the online hiring industry. It’s a must read for entrepreneurs and freelancers looking to stay on the bleeding edge of building multimillion dollar online businesses.

Question: How long have you two been working together?

We’ve been working together since the winter of 2010. We first met each other while studying at Quinnipiac University. We had the same Business Law class together and we ended up hitting it off. Nate had an idea for a business and messaged me one day to see if I’d be interested. I couldn’t reject the opportunity and it all took off from there. We never really looked back.

Question: What key advice do you have when starting businesses? Tell me about bootstrapping.

In our upcoming book, you’re going to get 50 best practices that we’ve developed over the past 7 years of working together. It’s going to be a really powerful book for growing entrepreneurs and business owners.

For this conversation, the biggest piece of advice that we want to offer is to stay open as you are getting your new business off the ground. As we started FreeeUp, we offered 3-4 different services because we wanted to see which stuck the most with our potential customers. As we landed more clients and listened to what they needed the most, we adjusted our core focus and eventually made that the main value prop of FreeeUp.

When starting a business, you never know which direction it is going to go. It’s so important to put a product/service out there and listen to your first customers. They will be the ones to tell you how you should make adjustments to your first version.

With regards to bootstrapping, we’re all for it. The two multimillion dollar businesses that we have built were bootstrapped. We invested small amounts into the start of each business (i.e. less than $5,000) and then intelligently used the profits from our sales to fund the continued growth of the business. When bootstrapping, you have to know your financials and you have to know them well. Each decision must be smart and contributing to the growth of the business.

Question: How do you hire the right people for your multimillion dollar online business?

It all comes down to the way that you recruit, interview, and test people before letting them into your business. With 7 years of hiring under our belts, we are meticulous when it comes to finding people to work with our internal workers. They must fit our perfect worker mold or they don’t make it through the first round of interviewing.

In short…create the exact outline of who you want for a given role, turn that into a job posting, post it in places where you know intelligent people are seeking jobs, spread the word through your existing community, schedule interviews with the absolute best, vet out people by asking the simple questions that meet your ideal mold of a worker, take it to the next step and test them on their culture fit and attitude, express your expectations of them and see if they can handle it.

If they’ve made it through all of this, take a few hours to onboard with them to see how they perform. Are they showing up on time? Are they learning quickly? Are they asking good questions? If they don’t wow you when working with them, don’t settle. Never settle.

Question: What key characteristics do you look for when hiring?

When hiring, it all comes down to skills, culture, and attitude. We want someone that is an absolute expert in their niche. They have a hunger for working and want to help the business grow. They are organized and respectful of other people’s time. They have a strong track record of working with other ambitious companies.

If you can find someone with this initial mold, there is a good chance they are a good fit for your company. We are fast movers and we like people who think outside of the box. And we challenge our workers all of the time. We need someone that is competitive enough to turn our challenges into accomplishments.

Question: What tactics do you use to motivate a worker once they are hired and set up?

We have a handful of tactics that we’re sharing in our weekly series on Getting the Most Out of Workers. One of the most useful is setting up daily check ins and weekly meetings with remote workers. Each day, you receive an update from workers so you know what they are accomplishing and where you can potentially help them.

Then you have weekly meetings where you can really dive into their work and push them to do more, push them to be even more productive. In the weekly meetings, it’s important to relate to them on a personal level and explain how their work contributes to the bigger goals of the company. No one wants to perform tasks day after day without a connection to their leader or an understanding of how it is helping the company.

Question: If someone was looking to start their own multimillion dollar online business, would you recommend they find a partner?

Absolutely. It’s a difficult dating process to find the right person, but if you can find someone that highly complements your skill sets then you are going to be able to get more done faster. If you look at us, we are very different in our skill sets and what we do for the company, but our business philosophies are extremely aligned. We trust each other to make advancements within our areas of expertise and we push each other to improve even more every day.

Having a partner also just adds to the experience of building a company. It can be a very lonely process if you are doing it on your own. No one to relate to that understands the weight of building a company from the ground up. No one to talk to about the tough decisions that you have to make as you grow the company. Having a strong partner by your side is key to long term success.

Question: Where do you see online hiring heading in the next 10 years?

The online hiring industry is such an interesting realm to be a part of right now. With it only becoming a huge move for companies to utilize starting in the mid 1990’s, there is still so much to be built and advanced upon. There are still thousands of business owners around the world that are skeptical of hiring remote workers or outsourcing because of the horror stories you can read on the Internet.

The industry is very much headed in the direction of speed and reliability. As with most discoveries because of the Internet, people want it to be faster and more reliable. Just look at the eCommerce industry and it will explain everything. We now want packages to be delivered within 2 days with a guarantee for returns and refunds if we don’t like the product. Just 15 short years ago, people were extremely skeptical of ordering online and there were only so many places you could order from.

In the next 10 years, we see the online hiring industry making adjustments so that introductions to workers can be made faster and the workers are more reliable. We see this as the trend and are starting to work towards it with FreeeUp. We don’t want our clients to have to post jobs, search for the best applicants, and interview. We want them to be able to submit a simple 10-question form and we introduce them to a pre-vetted worker within hours. That is speed that can make online hiring a huge advantage to businesses large and small.

Stay Tuned for The Secret of Strap

Stay tuned on social media (Follow on Facebook and Twitter.) for more updates on The Secret of Strap, to be publishing within the next couple of months. It’s going to offer 50 best practices for how you can structure and build your own online empire. These two have been doing it together for the past 7 years and they want to let others into the knowledge base that they have been able to create from their experiences and studies.

writer Melissa Ricker


Melissa Ricker is a nuclear engineer and a professional freelance writer specializing in career growth, technical writing and online entrepreneurship. She writes a blog, Engineered Motherhood, for working mothers who need help balancing career growth and time management. 


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