10 Financial Habits We Learned from 10 Years of Entrepreneurship


Do you have financial habits that you follow as your grow your business?


Do you feel like you truly understand your business financials?


financial habits 1


If I asked you “what’s your average expenses per month been in the past 3 months?”…would you be able to answer confidently?


How about this one…”What’s your trailing twelve months sales and profits?”


If you’re running an eCommerce business, do you know what percentage of your sales come from Amazon vs Shopify vs Ebay vs Walmart?


Likewise, do you know the products that are your best sellers and that make the most profits on a per unit basis?


If you’re running a software company, do you know the CAC (customer acquisition cost) and LTV (lifetime value) of your customers? How about your churn rate (amount of turnover)?


If you can’t answer these questions about your business, don’t worry!…I couldn’t either when Nathan Hirsch and I were starting to run our first business back in 2009.


There’s enough to worry about while starting and growing a new business…it’s hard to keep track of your finances as well…unless you have the right financial habits and systems in place.


In this article, I’ll share our top 10 financial habits that we’ve taken on over the past 10 years of being entrepreneurs and business owners. These financial habits are the result of starting and scaling four businesses (EcomBalance included).


The key to remember is that your financial habits and systems can always be improved. Never settle for where you’re at today and alway be looking for ways to improve your financial literacy of your business.


Our Experiences With Financial Habits


Before we dive into the 10 financial habits that we’ve developed over the past 10 years, I want to talk a bit about how it’s all come together.


Who Are We?


I am Connor Gillivan and my business partner is Nathan Hirsch. We met in college at Quinnipiac University in Hamden, Connecticut while both studying business. I’m originally from Albany, New York and Nathan is from Longmeadow, Massachussetts. We now both live in Denver, Colorado.


Together, we’ve started and scaled 4 companies so far. Our first business, Portlight, sold products on Amazon from 2009 until around 2016. With that first business, we learned the headaches of handling bookkeeping for an eCommerce business as we sold over $25 million in total sales over the 6 year period. For hours each month, we’d sit in a room reading out transactions and reconciling them in Quickbooks. We both still have nightmares of those Quickbooks sessions.


We founded our second business, FreeUp, in 2015. We saw a need for a better freelance marketplace specifically for Amazon sellers and eCommerce businesses and we set out to challenge the big boys like Upwork and Fiverr. FreeUp taught us a tremendous amount about properly managing our financials and truly understanding the numbers. At its peak, the business was doing $12 million in yearly sales from a client base of 1,000+. FreeUp was eventually acquired in late 2019 by The Hoth. I’m not sure the sale would have gone through if we hadn’t had all of our financials in such good shape. A true lesson learned in the importance of properly managing your books and knowing your numbers inside and out.


Our third business is Outsource School, an online membership educating business owners on our systems and processes for hiring and building teams of remote virtual assistants and freelancers.


After reflecting on which industry and problem we wanted to address next, financials and bookkeeping kept coming up. We had learned SO much over the 10 years of working on our first three businesses and we really saw how important they were when we went through the sale of FreeUp. From talking with hundreds of business owners over the years, we also knew that it was a piece of the business that others struggled with or hated handling.


That pain point we saw and which we validated with market research interviews led us to start EcomBalance. If we could help thousands of business owners better manage their books and know their numbers better, it would undoubtedly help them grow faster and smarter.


It’s been a 10 year journey of lessons learned and testing new habits to find the optimal financial habits that we could use day in and day out to best understand our numbers.


10 Financial Habits We Learned from 10 Years of Entrepreneurship


Disclaimer: We are not CPAs and we encourage you to follow up on all of this advice with a CPA that knows your business well.


Financial Habit #1: Never intermingle personal and business finances


If you’ve ever done this, you know why it’s one of the first habits we have. When you intermingle your personal and business finances, it can create an absolute mess in terms of bookkeeping and year-end accounting. It also makes it a LOT harder to see what your actual numbers are.


Think about it. If you have 1 bank account and 1 credit card that you use for all personal and business finances, how are you going to know what your business is actually making at the end of each month? Sure, it’s possible to go through every single transaction and classify them as personal or business, but that’s very tedious and completely unnecessary.


To avoid such difficulties, we recommend the following set up. 

  • Business checking account
  • Business credit card
  • Business PayPal (if you accept payments through it)
  • Business email account
  • Business accounts for all things related to business attached to your business email account


Put all of your business related expenses on your business credit card or through your business bank account. Likewise, have all of your revenue flow into your business bank account.


This will greatly simplify the financials of your business and make it possible for you to see an accurate look at how your business is performing each month.


Financial Habit #2: Always have someone that manages your bookkeeping for you and gets you reliable reports on time


financial habits 2This is one that we learned the hard way! As I eluded to earlier on, Nathan and I handled the books for our first eCommerce business for years before we passed it off to someone else. We always had a CPA that helped us with our year-end tax filings, but the month to month bookkeeping was on our plate. And we were always behind.


While we have spoken with some business owners that handle their own bookkeeping and don’t have any troubles getting it completed on time each month, we are strong proponents of passing it off to a reliable and experienced bookkeeper that knows your business model well. For example, if you’re selling on Amazon and Shopify, find a bookkeeper that has experience handling books for eCommerce businesses and that will understand the different transactions that flow through your business.


The most important part of this financial habit is to consistently get your monthly report on time. In general, you want to hold your bookkeeper to getting you the completed books by the 15th of each month. This gives them enough time to let all transactions settle and then provides it to you in a close enough window that you can make smart decisions based off of the numbers.


I can’t imagine how we would run our businesses without the help of our bookkeeping team and the on-time reports that they deliver each month. It’s honestly become such an engrained financial habit that it seems odd that it wouldn’t happen that way.


Here’s the set up we recommend: 

  • A bookkeeper or bookkeeping service that will manage your monthly bookkeeping in Quickbooks or Xero and will provide you with easy-to-read financial reports by the 15th of each month.
  • Based off of your preferences, a custom report showing your most important metrics and any big changes that you should be aware of for each month.


If you don’t have a bookkeeping set up like this yet, schedule a call with us at EcomBalance and we’ll talk you through how we can help you with it for an affordable price.


Financial Habit #3: Meet monthly to go over your financials from the past month


financial habits 3This financial habit is directly related to the previous one. Once you get those monthly reports coming to you consistently, it’s important to then meet with your co-owners or the most important people on your team to look at the books, assess how the month went, make goals for the next month, and see if there are any adjustments that need to be made.


For us, this is a simple, 30 minute meeting where we set up a phone or Zoom call. We both pull up the most recent month’s report and we go through our Profit and Loss Statement line by line seeing how the month went.


By the end of the 30 minutes, we have a very clear picture of what happened in the past month, where we need to make adjustments, and what we can expect for the following month.


This is an important meeting each month where we make key decisions about additional expenses, trimming costs, making new hires, forecasting revenue, etc. Without this meeting, we wouldn’t be as prepared to grow in the next month.


I can’t imagine how business owners go months without truly knowing what’s happening financially within their business. As a business owner, one of our most important duties is the financials. If we don’t know what’s actually happening, how can we optimize profits and grow the business?


Here’s what we recommend:

  • Agree on a day and time each month where you and your co-owners will go through the books from the previous month together. Add that into your calendars as a recurring event.
  • Spend 30 minutes each month going through your P and L, Balance Sheet, and Cash Flow Statement. Look for discrepancies over past months, talk about goals you have for the upcoming month, and compare how you’re doing to your goals for the current quarter and then for the current year.
  • Leave the meeting with action steps for how you’ll manage your finances in the next month and any key tasks you need to complete to make it happen as you’re imagining.


Over the past 2 years, we’ve brought a number of companies that Nathan and I have consulted for through this process and it’s drastically helped them better understand their numbers. This is also a part of the EcomBalance experience that we want to bring to life. We imagine monthly reports being delivered with real, actionable advice for our clients so that they can meet with their business owners and make smart decisions for the next month.


Financial Habit #4: Have clear 1 year financial goals for the business that you update and hold yourself to


financial habits 4Just like with anything in life, having goals helps to propel you towards that reality. The financials and profitability of your business is no different. In order to reach large levels of profitability, you need to set goals and work towards milestones on a month to month basis.


This has been a financial habit that Nathan and I have been strict about since the start of working together. We have 1 year financial plans that we’re always working towards and then we break them down into quarterly goals, monthly goals, and weekly goals. We use them as milestones for ourselves and for our teams so that we all have a collective outcome that we’re working towards. You’d be surprised of the power of an entire team of people working towards the same goal. From our experience, it greatly increases the chances of that goal becoming achieved.


Here’s what we recommend: 

  • Pick a time and day each month where you meet with your co-owners and leadership to discuss your financial goals for the business. This can coincide with the monthly Reviewing the Books meeting or it can be separate. We prefer it to be separate so that the meeting doesn’t go too long and we can really focus on each separate topic in each meeting. Get it on your calendars as a recurring event.
  • If you don’t have them already, create 1 year financial goals for each of your businesses. At a high level, these can be simple and focused on Revenue, Gross Profits, and Net Profits. For example, if you have 2 owners and you each want to make $100,000 per year, then your net profit may be $250,000 for the year. But it has to be realistic at the same time. There’s no point in making a goal to for $1 million in net profits if you just started your business. Look at how your business is trending and base your goals off of that.
  • Break down your 1 year financial goals into quarterly goals/milestones that must be met to reach the 1 year goals. For example, if your goal is to make $250,000 in net profit for the year then your goal per quarter is to average $62,500 in net profits. Now as you make your goals, you can also adjust that average depending on when your busy seasons are and where you’re currently at and how you expect net profits per quarter to grow over the next 4 quarters.
  • Share these financial goals with your team. Be transparent and open about where you want to see the business get to in the next 1 year and what everyone should be focused on in the next quarter. The more you get everyone on the same page, the better off you’ll be to reach your goals.
  • As you have your monthly Financial Bookkeeping Review meetings, look at how you’re performing with regards to your 1 year and quarterly goals. Are you exceeding expectations? Are you behind? Make adjustments to how you’re running the business based off of how you’re trending and comparing to your goals.


Financial Habit #5: Know your industry specific numbers


When running a business, it’s important to understand and track your industry specific numbers. These figures represent how your business is performing at a macro and micro level. They are different from your monthly financials that you see on your Profit and Loss statement, but they are important for understanding other aspects that ultimately impact your P & L.


Here are a few examples of industry specific figures that you should be tracking and understand:

  • CAC = Cost of Acquiring a Customer. This is the cost that it takes you to acquire a new paying customer. This figure is often related to advertising spending. So, if you spend $100 and get 10 new customers to sign up, your CAC would be $10 per customer.
  • LTV = Lifetime Value. This figure shows you how much money you earn from a customer in their lifetime of being a customer. So, if you have 100 customers over a 2 year period and, on average, you earn $1,000 from them as a group, your LTV for them would be $1,000 per customer. That’s a good figure to know as you make investments on the front end to acquire new customers. If you expect to make $1,000 off of them in 2 years, then it may be okay to pay $100, let’s say, to acquire them upfront.
  • Customer turnover = on average, how long a customer stays as a paying customer for you. So, if from 100 customers, they only average to be a paying customer for 2 months, that could be a problem and you’ll want to find out why they are dropping off after only 2 months.
  • Best selling products = If you’re running an eCommerce business, you’ll want to track your best selling products and also which ones are most profitable on a unit basis. For most eCommerce businesses, you make 80% of your sales on 20% of your products. Knowing what products are in that 20% is super important and will help you to increase sales further.


These figures are ones that you can hire a virtual assistant to help you in organizing or they could be reports that you ask your bookkeeper to create for you on a monthly basis.


Imagine looking at your financials each month and also having these numbers provided for you to see. You’d for sure be able to better understand how your business is trending and what moves you need to make to continue to grow.


Here’s what we recommend: 

  • Set up a meeting with your leadership team to go over what figures are most important to you as a business. Try to limit it to 5 key KPIs that you want to track on a monthly basis. These 5 figures should give you deep insights into how your business is performing so you can make adjustments as trends change.
  • Hire a bookkeeping service like EcomBalance to create these figures for you each month. Make sure that the numbers are coming through accurately and provide feedback as you get more figures that you want to see on a monthly basis.


Financial Habit #6: Over budget, expect extra expenses to come up


Always, always, always over budget. If you think estimate something might cost $100, budget $150 for it. Over-budgeting is a key skill to have as a business owner as it will put you in better situations where you end up having money left over that can then be spent or dispersed, as opposed to under-budgeting and running out of money.


One of the most common reasons that businesses shut down is due to running out of money. By applying the financial habit of over-budgeting, you help your business to avoid this scenario. Remember, your ultimate goal at the end of the day is to keep the business alive and growing. You can’t do that if you’re under-budgeting and getting into financial troubles.


Here’s what we recommend: 

  • Meet with your leadership team and discuss the major expenses that you have as a business on a monthly basis and what expenses you expect to have in the upcoming 6 months to 1 year. Lay them all out then talk through them setting a budget for each. Make sure to factor in how much cash you have, what the business is making per month, and build a conservative budget from there.
  • As you have your monthly financial meetings, review the budget, look at how much you’re spending in each major category, and make adjustments as needed. For example, maybe you see that one month you spent more than you had budgeted for marketing efforts. Well, if sales and profits didn’t increase as a direct result, you may need to lower the budget for marketing in the following month.


The same goes for projections. Under project on your sales growth. This is one of the most common mistakes that entrepreneurs make when scaling a business. They set unrealistic projections for how much they’ll be making and then they raise their budgets as well. When the sales don’t show up, they end up losing money and have to dig their way out of the hole.


Financial Habit #7: Pick a few people you are comfortable talking about money with.  Share ideas, strategies, and new things you come across.


financial habits 5Running a business doesn’t have to be a solo mission. Throughout our years of building, we’ve always surrounded ourselves with other smart people that we trust and that have more experience than us. You can do it in a more formal way where they become advisors to your business or you can do it in a less formal way where you find a group of people willing to be a mentor to you and the business.


This is an individual or a small group of people that you can share problems and questions with when it comes to your financials. As a business owner, it’s unrealistic to think that you’ll know the answer to everything, especially when it comes to your finances. When you have someone that you trust and you can go to every month or quarter with questions and roadblocks, it lessens the burden on you personally and makes the situation better for the business overall.


Here’s what we recommend doing:

  • Find 1-2 people that you trust and look up to when it comes to finances. This could be your business partner, a parent, a family member, or someone that you respect and have networked with in your industry. Ask them if it’s okay for you to come to them with financial questions and roadblocks as you have them with your business. Let them know it won’t be time consuming and will only be an email or phone call here or there every quarter or so.
  • Once you have 1-2 people committed to supporting you, make sure to tap into their knowledge. If they want, include them on the monthly reports so they can see how things are trending in your business. And set a reminder to reach out to them at least 1x per quarter to ask them questions and talk about roadblocks you’re running into. An outside perspective will work wonders for you as a business owner. It’s also a financial habit that will drastically help your business in the long run.


Financial Habit #8: Don’t take financial or tax advice from social media posts. Hire a great bookkeeper and accountant.


This one should go without saying, but there’s a LOT of noise out there on the Internet today. Please do not take financial advice from anyone on social media. Even if they state they are a reputable source, take the time to find a reliable and certified bookkeeper and accountant that you can lean on for financial questions.


Personally, Nathan and I have been working with the same Accountant since we started our first business 10 years ago. I can’t tell you how valuable it has been to have him in our corner as we’ve gone through all sorts of different events within our businesses. From tough questions about employees to the acquisition of FreeUp, he was there to support us and answer all of our questions.


If you’re worrying about the expense of a bookkeeper and accountant, don’t worry. You can make it affordable. There are bookkeeping services out there like EcomBalance that start as low as $150 per month for full service bookkeeping. And for an accountant, the best way to set up the relationship is on an as-needed basis. You pay for their time when you need to talk to them and you pay them for the tax filing work they complete for you at the end of each year. Very manageable.


Here’s what we recommend you do:

  • If you don’t already, take the time to research and find a reliable bookkeeper and accountant for your business. Check out EcomBalance for our bookkeeping services. We can also recommend reliable Accountants that we have worked with for years. You can also reach out to your community to ask who they have had the best experience working with.


Financial Habit #9: Ignore the news or anyone predicting the future. No one knows the future.  Any decision you make is a risk.  Make decisions based on the information you have, the story it’s telling and stick with it.  Focus on the decision making process more than results.


Numbers don’t lie. When making decisions for your business, make sure that you’re looking at your numbers and you’re making smart, informed decisions based off of them.


There’s a lot of noise on social media and in the news that could alter your decisions or ambitions for your business. Don’t let them stand in the way of your obligation to make the best possible decisions for the long term growth and profitability of your business. Don’t get distracted and stay focused on the facts in front of you in the form of your financials.


When you apply this financial habit and turn on the blinders, in a sense, to the outside world, you’ll better understand your business and you’ll be in a better position to make smart decisions for your growth.


This has been something we’ve always battled with as we’ve grown our businesses over the years. News about something or another can drastically impact how you think about your business, its trajectory, and how you want to move forward.


At the end of the day, you have to remember that your job is to do what’s absolutely best for the business and that those decisions should be based off of how the business is performing and trending. As we said above, it’s smart to have some mentors or advisors on your side that you can consult with when the times get tough, but ignore the outside noise and stay focused on what you can control.


Financial Habit #10: Write down your financial habits and evaluate them every year


financial habits 6For the first few years of being entrepreneurs together, a lot of our financial habits just fell into place through trial and error. We’d run into a specific situation, we’d problem solve the best possible way to solve it, then we’d continue doing that. We never truly formalized our financial habits until a few years in.


When we decided to actually write down our financial habits and hold each other to them, things got even better. We had “rules” that we had seen success with using in the past and we committed to using them for all of our businesses going forward. And not only using them, but also reviewing them and finding new financial habits that we could add into our repertoire.


Being an entrepreneur and business owner means constantly learning and adjusting. Never become complacent as it will eventually hurt you and your business.


Here’s what we recommend:

  • Sit down with your founding team and go over the financial habits you want to follow together. Some of them could be from this article that you want to start implementing. Whatever those financial habits are, commit to it, put them in the calendar, and write them down somewhere that you can easily access and read them. The more you see them and read them, the more engrained they’ll become within your psyche.
  • Every 6 months to 1 year, have a meeting specifically to go through the financial habits. Look for improvements, talk about how they helped, and bring up any new ones that you want to add to the list.


The more you develop your financial habits, the better they will become over the years and the better off you’ll be as a business owner looking to grow and create more profits.


In Conclusion


In this article, we’ve shared 10 of our most valuable financial habits that we’ve developed over 10 years of being entrepreneurs together. We’re now applying them to growing our two companies, EcomBalance and Outsource School. It’s our goal to continue developing them so that we can become smarter with our financials for our ventures. As I said above, it’s critical that you never stop learning and adapting to what your business needs from you.


If you’re interested in working with us to handle your bookkeeping needs, you can sign up for a free month and learn how we do business with our clients. You can also review EcomBalance Pricing. You’ll see that we cater to businesses of all sizes and that we customize all of our tiers to best fit each of our clients.


Lastly, if you have any questions about these 10 financial habits, post in the comments below or reach out to us at [email protected]. We’ll answer your questions quickly and will add to this post as we come up with other financial habits that we find worthy of joining the article.


Thanks for your time! We hope that these financial habits will help guide you and your business to profitability and better financial understanding. Cheers!

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Connor Gillivan

Connor Gillivan

CMO and Founder of EcomBalance. Founded FreeUp (acquired in 2019). Founder of Outsource School. Published Author. Investor.

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