Free Up Your Business with Nathan Hirsch

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TBT 13 | Outsourcing Platform

As a broke college kid looking for extra beer money, Nathan Hirsch, CEO of, an outsourcing platform, was running a million-dollar baby product business from a college dorm room. His business exploded and soon he found he needed some help. Nathan took advantage of remote hiring and became addicted to it because he saw all the potential and had access to talent from all around the world. His time shifted from expanding and growing his business to doing interviews and hiring people in a faster way. Nathan shares the one thing he learned early on was that trying to do everything yourself will backfire and fail on you. Getting that 360 degree perspective from diverse people working for you can help you identify the blind spots so you can make every minute productive.

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Free Up Your Business with Nathan Hirsch

We are with Nathan Hirsch, CEO of, successful entrepreneur, and influencer on ecommerce platforms and whatnot. He created from his dorm room in college his first $20 million business called Portlight and he’s now the CEO of, which is an outsourcing platform. It is making people more efficient and effective, which is what I’m all about. I’m super excited to have you here, Nathan. Welcome.
Thanks so much for having me. I’m excited to be here.
How did you become the outsourcing guru? How did you fall into this space?
I started off as a broke college kid looking for extra beer money and I started buying and selling textbooks on the side to cut out the bookstore that I thought was ripping me off. Before I knew it, I had lines out the door of people trying to sell me their books to the point where I got a cease and desist letter from the school telling me to knock it off because I was stealing their business.
You know you’re doing a good job when you get that.
That was my first taste of being an entrepreneur. From selling books, I learned a little bit about Amazon. This was back in 2008, 2009, so Amazon was just expanding to be more than a bookstore and I became addicted to it, obsessed with it. All I wanted to do was become an Amazon seller. I started trying to sell cool products, sporting equipment, DVDs, video games, and I failed over and over. I couldn’t get anything to sell besides books. One day, I came across this deal on baby products and I started experimenting with baby products, and it took off. Before I knew it, I was running this million dollar baby product business as a single college guy in my college dorm room.
As this business exploded and I’m being faced with every obstacle that a young entrepreneur faced, the biggest thing was, “Who do I hire do all this work?”At 21 years old, I’m going through this journey and I learned about the remote hiring world after hiring a few internal employees. I became addicted to that because I saw all the potential that I had access to talent from all around the world. I could pick and choose specialists. I could diversify. I could build teams of remote freelancers. All of a sudden, my time-shifted from expanding and growing my business to doing interviews and hiring people all day, and so I wanted a faster way. That’s when I got the idea of building a marketplace where we pre-vet people and let the top 1% in and give people fast access to talent. That’s how I went from a college kid to starting two companies.
One of your major issues is that you couldn’t do it all yourself? You had to find quality people?
Trying to do it all yourself will backfire and fail on you. That’s one thing I learned pretty early on.
We all know that as entrepreneur, because we’ve all had challenging situations with that. Tell me story. Did you do it yourself and it cost you dearly? I want other entrepreneurs to get this point. They’re not doing themselves any service by trying to do it all themselves.
A lot of it came early on was customer service because that was the Amazon business. It was all about customer service and I would drive myself crazy. I was answering every email around the clock, Saturday mornings, Sunday mornings, trying to get that response time down, trying to make every client happy and all of a sudden, the business stopped growing. I just give up because I wasn’t getting new products. I wasn’t building new relationships. I wasn’t learning new things that are happening on Amazon.

TBT 13 | Outsourcing Platform

Outsourcing Platform: Focus on short-term projects that you can do to help get your business to the next level and slowly and slowly reinvest back into your company.

I was stuck spending half my week doing customer service emails, doing returns and it was so hard to give that up, but eventually, I realized the business was flat lining and the only way that I could take it to the next level was by kicking customer service off my plate. I remember the first day after I trained someone for a few weeks our customer service. I woke up and I turned off emails off on my phone and it was a fantastic day. I couldn’t believe it. I no longer had to worry about customer service. Over the next few months, my business took off because I was focused on growing and aggressively strategizing how to get bigger instead of those routine day to day operations that if I had enough force myself to get out of, I would’ve been stuck in it for who knows how long.
Your business would be out of business, because you’re not focusing on growing the business.
Eventually, someone’s going to come in and you’re going to start going backwards fast.
A lot of people face that struggle. This in your book Free Up Your Business. You say to reduce risk and to be cautious with your cashflow. Sometimes people are a little bit stingy with their cashflow and they say, “I don’t have enough money. I don’t have enough resources. I can’t outsource because I don’t have the cash.” What would you say in that context?
If you’re still in that trial and error phase, if you don’t have a proof of concept, if you don’t have any revenue stream, you shouldn’t be going around hiring people. You should figure out your business first, but once you get that revenue stream and you’re starting to grow, think of it more as short term projects. Think of it more of getting a few hours of your day back. What would you do with an assistant that worked 8:00 AM to 10:00 AM, so that you got caught up in the morning and you could focus the rest of the day on expansion? Instead of spending the next three weeks figuring out how to build a website yourself, hire someone to crank it out in a few days. Focus on short-term projects that you can do to help get your business to the next level and slowly and slowly reinvest back into your company and slowly your business will start to grow faster and faster and then you can reinvest more.
Sometimes we feel like it’s an all or nothing. I have to hire somebody full-time and there’s many great expertise that you can buy at a couple of hours of time. You can get an expertise person in social media or marketing or project manager or right in all these different areas that can help you to take back time, so that you can focus on what you’re best at.
One of the best meetings that I had with my business partner Connor, is we sat down and we made a list of everything that we’re good at and everything that we were bad at. We were brutally honest with each other. “You’re a terrible writer.” “You think too far in the future, you’re not focused on what’s going on either.” Brutally honest and it was painful at first, but at the end, we had this great list and we could delegate between each other, so we weren’t stepping on each other’s toes. We also had a list of things that we’re both bad at, and so we started hiring for those things, turning weaknesses into strengths. That was such an important growing our first business and it’s an exercise we still go through today because we know how powerful it is.
One great thing that an entrepreneur can do, either a solo entrepreneur or within a team, is once they’ve figured out their business is to do a SWOT analysis. A strengths, opportunities, weaknesses, and threats, so that they can get clear on where they would be best off outsourcing and where they want to focus their time and energy. That’s a concrete thing that everybody could do. Take a piece of paper and make four quadrants and identify what are their strengths, what are their weaknesses, what are their opportunities, and what are their threats?
You don’t have a good grasp on that for your business. You have to spend time figuring that out because it’s hard to make decisions. It’s so hard to prioritize what you’re doing when you don’t have all the information. Just laying all the information out there for you and your business partners to see and you think getting other people involved. If you already have employees, if you’re already hiring contractors or freelancers, ask them for their opinions because sometimes you don’t see whole picture. You don’t know what’s going on in every part of your business and they can help provide information that you can then base your decisions and you’ll prioritize it.
[Tweet “It’s so hard to prioritize what you’re doing when you don’t have all the information.”] That’s why we have to do it. It’s because we all have blind spots and we’re fooling ourselves if we think that we don’t. You and your partner did it together because he’s going to see things that you don’t see or that you don’t want to admit. Your suppliers and your employees get that 360 degree perspective. You talked about prioritization. Chapter five in your book was Make Every Minute Productive. I was excited to get to that chapter, being a little bit excited around productivity and making things more efficient and effective.
The chapter was around prioritization and I’d love to know what are a couple of practical tips that you would advise people around creating priorities. One of the key things that people come to me a lot about and we talk about and I’ve got some tips and tools, but they’re struggling with everything is urgent. We live in a society where we get a text and we read it within 30 seconds and we respond within 90 seconds. What are some of the tips that you would advise people with all the years of experience and the ups and downs and failures and successes that you’ve had?
There’s many different factors when it comes to prioritizing. One of the factors that people don’t think about is the length time. If I have a bunch of short-term projects, even if they might not be tip top priority, but a bigger project is priority. It might make more sense for you to crank those out first just so they’re done. That’s one example, but a lot of it is comparing. I have it on my Trello and my Trello is broken down into day to day stuff, into short-term projects and into long-term projects. As I’m coming up with new things, I’m throwing it in there, but then every day I’m reorganizing it and if a new thing comes up, I’m shifting and I’m moving boxes around.
For me, I’m always trying to figure out, “How does this compare to this?”Factoring in whether it’s long-term or short-term, factoring in what the ROI is, factoring in what resources I’m going to have to spend? What the budget is? Do I want to spend that much? Also, the success rate because if it’s something that I know is a sure thing to help my business, something that’s worked in the past, something that working for my competitors, I’m going to prioritize that over something that I’m trying out that may or may not work that’s an experiment. I love experimenting. I love trying and daring different things, but at the same time, you want to prioritize things and you know you’ll get that ROI out, especially early on in the business.
You’ve got a number of different factors that helped you make that comparison. It’s like a criteria that you can say which factor is more important than the other. It may be short to do, but maybe somebody else can do it. You’re weighing those factors and you use Trello. Is that your tool of choice there?
It is my tool of choice and you do have to look at all the factors. I always look at the length of time or people I can give it to, how urgent it is. Let’s say it’s a bug in our software that’s affecting all of our clients top priority over everything. It’s maybe a small issue. If there was an urgent thing that’s affecting our clients, it goes to the top of the list. If it’s something that I’m unsure about, it might be a little bit lower than something I know I’m getting an ROI, something that’s proven, I’m going to do it. I’m going to move it up. I’m always trying to compare projects to each other and also figuring out, “Who can I hire to do this? What can I afford to get off my plate? Is this something that I’m good at or is this a big waste of my time?”
Something that I do often is the alternative, I value my time. I know that this was in your book as well. I know what the value of my time is and what an hour could mean in terms of income that I could be bringing in if I was focused on a strategic project. I also have to take that into consideration when I’m looking to outsource. That I can be gaining back that time, so I can be creating revenue. What’s my opportunity cost with each thing that I do myself? That’s something that I look at when I’m evaluating priorities as well.
Just like you have to have full control of your SWOT, you have to have control over your financials. You have to know what’s going on. You have to get to know your team very well. What are their strengths? What are their weaknesses? What can they actually contribute? How are they using their time and spending their time? Are you noticing what’s going on in the market around you? What’s the demand? What’s working? What’s not working? There’s much information that you have to use when prioritizing, when problem solving, when hiring, that you want to make sure you have as much as possible before you make those business decisions.
One of the things that I find that people do, not all tasks are created equal. That’s why we can prioritize at the end of the day. What about strategic thinking? You need to get your head around something and you need to think, you need time to think, and that’s the thing that nobody makes time for. It’s a dead art, thinking, but it’s so important to grow your business. How do you fit that into prioritization?
I like to get away from my business. The only way that I can do it is turn the phone off, get the laptop away from me, and I’ll meet with my business partner, Connor, just away. Maybe I might be at a dog park because I have a dog or I might be at the beach or at the lake and away from the business once a week and talk. Brainstorm and shoot ideas back and forth, but also have an agenda that you’re going through to make decisions, to talk about strategy, to talk about prioritization. He might have a different opinion than I do and we’ll talk it out and move forward once we get on the same page. That’s important because as a business owner, it’s easy to get caught up in the day–to-day operations, especially as you’re growing and you’re starting out, but you have to take that time each week. Even if it’s an hour to look at the big picture, look at the future and come up with some good strategies.

TBT 13 | Outsourcing Platform

Outsourcing Platform: If you already have employees, ask them for their opinions because sometimes you don’t see whole picture.

People don’t take the time anymore. That’s why they get stuck in everything urgent. That’s the curse of the entrepreneur. Urgency is a good thing and that’s why they provide great customer service and they’re growing their business, but at some point, it becomes an over the top problem. What I want people to realize, and you put this clearly and nicely in chapter five of your book, is there’s that weekly prioritization that you do, which is done from more of a strategic level of looking at all the projects looking across the week.
Then there’s the daily prioritization that you’re going to either look at with your team or yourself, depending on who it is that you’re managing. Then there’s the on-the-fly prioritization. I find that that frazzles people a lot. They say, “I don’t have a schedule that allows me to be structured and it’s not routine,” so they get frazzled that things change a lot. What’s your advice around that or your counsel to people who feel like, “I don’t have a routine schedule. It’s hard for me to prioritize,” and they’re stuck in that excuse.
I don’t have a routine schedule either. I don’t know what routine is. Every day is different. The way that I do it is I have a team of people that are great. If I’m running behind on phone calls, I can say, “Can we take this call so I can handle this issue or vice versa. You handle the issue while I do the phone call.” I’ll delegate throughout the day and it’s all about communication. If I have two assistants that are on, we’re constantly talking, “I’m swamped. I have to figure this out right now. I’m busy for the next two hours.” “I just finished that last project. What’s next in priority?”
We have that communication flow going or delegating where we’re prioritizing, “What’s more important, this client call or this issue?”Not that client calls aren’t important, but there are other people that might be able to take that client call and still give a good experience. We’re constantly trying to figure that out. We’re also keeping open communication with all those outside factors. If it’s a partner that has to talk to her client or a new vendor, we try to be open, honest and transparent. “I’m free in 1.5 hours. Can we talk then?”“Do you have an opening tomorrow morning?”“Let me wrap this up?”
You actually have the nerve to ask a client or tell them that you’re not available immediately and that you’ll make an appointment later?
Yes, and you’ll get those clients who are like, “No, I have to meet now,” and that immediately changes that prioritization. You go to that podcast, I was two minutes late for the podcast, but I communicated, “I’m wrapping something up but I need another two minutes.” Will there be a perfect balance and you always get those two things scheduled at once. You have to make it off and apologize and make it right but it’s part of being a business owner and I strongly recommend using Calendly to have your schedule built out as possible, but also leave room for those adjustment periods.
What percentage? You asked somebody, your client, internal staff, whatever it is, you ask them if you can move it? You have that level of open communication and you understand the power of questions to free up your time and reduced stress. What percentage of time? I want people to understand that even though clients are important and their issues matter, we don’t have to address them immediately every time. What percentage of clients say, “I can meet in two hours or I can meet tomorrow?” 
[Tweet “I am a big proponent of speed because the best way to solve a problem is to address it quickly and it gives you a huge advantage.”] Almost all of them, but with that said, I am a big proponent of speed because the best way to solve a problem is to address it quickly and it gives you a huge advantage. We’re pushing people off. If I can’t meet, I can’t meet. If you and I had this podcast scheduled for a month, I’m not going to cancel a podcast because something came up that doesn’t make sense, and clients will understand that.
That’s the point that I’m making is that we make our self frenzied and we get stuck in that emotional of, “This is all urgent, I don’t know what to do.” Then we go into overwhelm and we shut down, and our problem-solving skills have gone right down to zero because we’re in fight or flight in our brain versus in problem-solving mode. The easiest way is to communicate is to ask a question. How important is this?
 You either ask the question to yourself so that you can answer it and give it a criteria or we ask those that are involved, because what I found when I had an IT business, if it was something that had a whole department down or something, then it was immediate urgent, but it didn’t mean that I had to do it. I found that when I spoke and asked questions, I was able to find out, and very often, it was my assumption that it was urgent. They would say, “That’s fine. You can get back to me tomorrow on that,” or, “I don’t need this until next week.”
I’ll even say, “Can I get all the information? Give me some time to research it, to fix it and I’m going to value your time. I’m just going to come to you with the solution.”Sometimes that’s even a great way to approach it where it buys you a little bit of time but the client knows that you do have their best interests at heart.
It’s all in the communication. These were some awesome tips around prioritization, around understanding also how we can utilize outsourcing. As people are rethinking, as you’re doing your SWOT analysis and understanding where your strengths and weaknesses are, you’re evaluating what’s priority in your business, what the value of your time is, and how you can take back some of that time through utilizing some valuable resources in outsourcing, project by project, a few hours at a time to give you the space to grow your business. I’ve been through that matching process and I liked it. I thought it was a fast, seamless process and I was able to get the skills that I was looking for with the people from the platform. The more you get some experience, the more you’re going to use something, so you have a good experience and then you’re going to find other ways. Like you said, you have two assistants. Some people have four assistants for different skill sets that they’re utilizing.
Thank you all for being here. I hope that you took away a few nuggets that are going to help you to reduce some stress in your life, to be more structured in your prioritization. Also, to consider outsourcing as a way to help you take back time and be able to grow your business, spend more time with family or whatever it is that’s important to you.

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About Nathan Hirsch

TBT 13 | Outsourcing PlatformNathan Hirsch is a serial entrepreneur and influencer within the eCommerce and entrepreneurship world. He co-founded Portlight out of his college dorm room and served as the COO building the company’s systems and processes that helped generate over $20 million in product sales and over 1,000 supplier relationships. He is a co-founder and the CEO of FreeeUp where he leads all efforts of growth for the company especially in landing new clients for the platform. He has been featured on leading podcasts such as Entrepreneur on Fire, The Eventual Millionaire, and many more. He is from Connecticut and currently resides in Orlando, Florida.

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