Next month marks 20 years since I first opened the doors to my law firm. In that time, I’ve lost a lot of money on failed business ideas, bounced back, taken two bar exams, moved states, hired staff, lost staff, and learned more life lessons than I can count. Here are 20 of the top lessons learned in business that I would like to share with you.
Entrepreneurship has been the greatest adventures of my life. It’s shaped who I am and the man I’ve become. My business has given me freedom to lead an extraordinary life, live overseas, and taught me things that no classroom ever could.
Making it to 20 years in business is an amazing accomplishment, as only about half of small businesses survive 5 years, and fewer than one in five last two decades. So the fact that I have made it this long puts me in a tiny group of small business owners.
Today I want to share with you 20 of the biggest lessons I’ve learned along the way about both business and life. And to make this post a bit more palatable, I’ve broken my tips down into a number of categories, including: mindset, personal finance, relationships, marketing, and business operations.
If you would prefer to listen, I broke this blog post down into 2 separate podcast episodes.
Mindset and Personal Growth
If you don’t have the right mindset to run a small business, chances are you won’t be successful. Building a business is a long term exercise and there is a very good chance you will run into some tough times along the way. This is why I’m including these mindset tips as some of the top lessons you need to be thinking about as you embark on your entrepreneurial journey.
1. The only constant is change.
The business you start is rarely the business you’ll be running 5, 10, or 20 years later. Adaptability is the key to survival. When I started my law firm, I was a criminal defense lawyer (that lasted about 3 clients and less than a year as I just never felt comfortable in that role). Then the attorney I rented space from started sending me “domestic” work, which is a fancy way to say he had divorce cases he didn’t want. I found my niche in family law and managed to build a nice little practice. I even wrote a couple of books on the topic.
But after several years, I began getting burned out. It turns out that divorce brings out the worst in people, and all that negative energy was transferred to me. So I dabbled in some other practice areas until I finally started working with business clients about 8 years ago, and finally niched my practice down to handling only trademarks a few years ago.
Like I said, the only constant over the long run is change.
2. Learn to say no.
Not every client, project, or opportunity is the right fit for you. But when you first get started in business, the thought of telling someone that you can’t (or won’t) work with them is extremely scary. This is especially true if they are ready to pay you a lot of money. But trust me when I say this – tackling projects you aren’t passionate about just because of the money can quickly turn into more trouble than it is worth. You must trust that projects you do enjoy working on will fill the void left by the projects you say no to. Saying no creates space for the work and people that truly matter in your life.
3. Always keep learning.
I make it a habit to read or listen to at least one business, marketing, or sales book every month. I have had a subscription to Audible for years now, and have read a ton of books as a result. If I find a book that I really like, I will also purchase the physical copy of the book to mark up with a highlighter. My bookshelf is filled with amazing books that I still refer back to and recommend to others. Continuous learning keeps your ideas fresh and your edge sharp. I’ll share my top 20 business books in a future post, but in the meantime here are 5 of my favorites.
- Endless Referrals by Bob Burg
- Never Eat Alone by Keith Ferrazzi
- The E-Myth by Michael Gerber
- The Simple Path to Wealth by JL Collins
- Profit First by Mike Michalowicz
Of course, mindset is only part of the equation. If you don’t get the money side of your business right, the rest won’t matter.
Money and Finance
There are many reasons that people go into business for themselves. Some people crave lifestyle freedom, others believe that starting their own business is the key to riches. Some people are just functionally unemployable and have no other choice. Regardless of the reason you may be thinking about going into business, there is no denying that you need your business to provide you with financial compensation (unless you are already financially independent and are just looking for a fun hobby).
Not to mention, if you get the money stuff right from the beginning, you are setting yourself up for success regardless of how well your business does or how much revenue you generate. Over your years of business you are going to have years where you are financially successful, as well as years where you may constantly feel like the walls are caving in on you financially. If you follow these important lessons, you will reach financial freedom eventually.
4. Save for retirement early and often.
As a business owner, you don’t have an employer who is setting up your 401k and matching your contributions. You need to do this on your own. But the nice thing about running a small business is that there are several amazing retirement planning options available to you that will allow you to contribute up to $70,000 per year (in 2025) to your retirement account. My recommendation is that you contribute as much as you possibly can each year.
Most people neglect this one piece of advice and come to regret it over time. Max out your retirement contributions every year. Even modest, consistent savings can turn into (multiple) seven figures over time and set you up for true financial freedom. I was never consistent about this (which I now regret), but starting and funding a SEP IRA was one of the best decisions I ever made.
5. Avoid debt and watch your business expenses like a hawk.
Early on, I made the mistake of financing things I didn’t really need. I spent thousands of dollars on a yellow page (remember those?) ad that didn’t turn into a single client. I spent hundreds of dollars on expensive letterhead that really wasn’t necessary. And I financed all of this on a credit card with the assumption that I would pay it off with a couple good clients.
Debt is a weight on your business, and unnecessary expenses are just as dangerous. Monitor your bank and credit card statements vigilantly. Keep your overhead lean. When in doubt, ask yourself: “Is this an investment or just a shiny object?” If you spend less money on shiny objects, it gives you more freedom to invest in your retirement (see tip #4) and will allow you to weather the slow months when there isn’t as much revenue coming in.
6. Live beneath your means.
Along with tip number 5, you need to keep your personal expenses lean as well. Personally, I follow the profit first methodology and pull out a percentage of my revenue (after I pay my staff) for owner pay. I also deposit 5-10% of our revenue each month into a profit account and another 10-15% into a tax account. If I have a good month, that means that more of my revenue goes into savings. And not only that, I also take 10% of the amount I pay myself and put it into a personal investment/savings account.
By doing this, I’m constantly adding to my nest egg in the event something goes wrong in the business or I have a few lean months. Cash is king when you are running your own business and will allow you to easily say no to opportunities that don’t match up with your values or priorities.
7. You don’t need to make a million dollars.
This one took me a long time to learn. For many years I felt like my success was tied to the revenue of my firm. And for some entrepreneurs, earning a million dollars or more per year is the ultimate goal. But where I am at in my life, I realize that you can have a very comfortable “lifestyle business” that supports you and your family without making 7 figures per year. And oftentimes, this type of business can be just as rewarding or even more so than running a huge enterprise with a lot of overhead and a lot of stress.
This past summer I got together with three of my closest friends from high school. We are all at various stages of our entrepreneurial journey and all are at least partial owners of our own businesses. After we got back from a day of eating and drinking, we were having some beers and chatting about business around a campfire. One of my friends was frustrated about a number of things related to his business and worried about how the current political climate may impact him. We all made some suggestions for how he could weather this storm, but he kept coming back to the idea that he wanted to make more money. He is a successful entrepreneur in his own right – he had already revealed to me his net worth and financial goals. So I asked him why he was still working (frankly, he had enough saved to retire if he wanted to) and what his goals were. He just kept saying that he wants to make $X amount of money per year, and wants to have $X amount saved, but he didn’t have a good reason why. It just “seemed like the right thing to do”.
I would challenge you to rethink your thoughts about money. Yes, having money is necessary to achieve financial freedom. But you don’t need $100 million in the bank (or even $10 million!) to accomplish that. Focus on what is important to you, figure out what that costs, and then plan your business around making enough money for you to enjoy your life and save for retirement.
8. Plan for early retirement.
Which leads us to this important tip. You should be saving and planning for retirement from the first day you start your business. And to be clear, by “retirement” I don’t necessarily mean that you stop working. In my version of retirement, I’m able to work as much or as little as I want. I have enough income from my investment portfolio to pay my living expenses. I can travel freely and take time off when I want, without worrying about my business. This is something that I think everyone should strive for. And if you are contributing to your retirement accounts each year, you will hit financial independence sooner than you realize.
Clients and Relationships
As a law firm owner, I have lots of clients. My best clients come back to me for new projects and refer their friends and business colleagues to my firm. You MUST prioritize a culture of building strong relationships and creating an amazing customer experience. Believe it or not, when you do this it gives you a competitive advantage over your competitors who may just be relying on paid ads to gather new business.
9. Treat your clients like family.
You will quickly learn in business that all clients and customers are not the same. 20% of your clients will bring you 80% of your happiness in business and will make your work truly amazing. But the bottom 20% will cause 80% of the problems, refunds, and chargebacks of your business (which hopefully will be minimal). Do everything you can to treat your clients like family. Be responsive. Send little welcome gifts when you are hired for a large engagement (or finish a large engagement). Proactively reach out and tell your clients what is going on with their case or the work you are doing for them. Use systems and checklists so that you don’t forget to follow-up. These small little gestures will go a long way to generating referrals and repeat business alike from clients and customers that know, like and trust you.
10. Provide more value than you’re paid for.
I’ve always made it a point to tell clients that I don’t want to take their money if I can’t provide them at least as much value in return as the amount of money they are paying me. People pay you for the value you bring to their lives. And if you are a service provider as I am, this is typically because you are providing them with a service they can’t do on their own. Or if they could do it on their own, it would take them way longer and would be way harder to finish than if they hire you to help them with it.
There are certain things I just can’t (or won’t) do. Like cleaning out my gutters (I tried to once, fell off the ladder and ended up in the emergency room) or wildlife removal or painting (I HATE painting)! If you love doing what you do and other people don’t love doing that thing, then they are likely to pay you to do it for them. But the businesses that do the best deliver results on time and professionally in a way that you can’t wait to tell your friends how much you loved the experience of working with that business. When you give people more than they expect, they become your biggest advocates.
11. Hire help sooner than you think.
I have struggled with finding and hiring the right people for my law firm. I’ve gone through a number of different legal assistants over the years. When you find a good one, you want to keep them and your business will flourish as a result. You can’t (and shouldn’t) do it all yourself. Remember, you only need to pay them for the next month, not the next year. But the right employee is worth their weight in gold. I’ve had great employees and horrible ones, but one of the best lessons I’ve learned is to hire sooner than you feel comfortable. The right hire will free you up to focus on doing more marketing and building better products and services for your clients or customers.
Marketing and Growth
Marketing is the lifeblood of any successful business. If you aren’t marketing, you aren’t growing your business. Whenever I talk to people who are struggling to make sales, I ask them what they have done to market their business lately and the frequent answer is… nothing. So here are a few lessons I’ve learned over the years that you as a new business owner should pay close attention to.
12. Never stop marketing.
Pick one platform and show up consistently — YouTube, podcasting, blogging, email. The key is consistency, not perfection. This is one lesson that I wish I had handled more consistently.
I posted my first Youtube Video back in 2016. I posted regularly for a few months and then stopped. And not only did I stop, but I also stopped paying attention to the channel which started to grow based on my original videos. I started noticing comments and then found out my channel had almost 10,000 subscribers. This took about 2 years – and I always wonder what could have happened if I hadn’t stopped publishing.
So the big picture lesson here is that the most effective marketing is consistent marketing. It is a lot of work and will take you a lot of time, but slow and steady is a great way to build your business.
The main takeaway here is that you need to pick a channel and be consistent. I would focus on producing content that will resonate with your target market or target audience and post it on the platforms where those potential customers and clients are most likely to hang out. This is the best way to grow your new venture organically over time without spending a lot of money on ads.
13. Build and nurture your email list.
Social media platforms come and go, but your email list is yours. It’s one of the best assets you can build. As you are publishing your content on a regular, consistent basis, you should be giving people an opportunity to hop on your email list. People have become more reluctant to hand over their email in recent years, but if they are a hot lead and they need (or want) what you have to offer, they will gladly give you their email in exchange for some value from you.
The key here is to determine what that value may be. There is a learning curve involved, but you can test out various ideas such as checklists, white papers, videos or even webinars that provide information about the problem you are solving for your prospective customer or client. Once you get people onto your email list, you can continue to send them information and tools that will bring value to their lives. Also, they are more likely to remember you if they see your emails on a regular basis. Is building and nurturing an email list hard work? Sure it is, but when you get to the point where you can send an email and generate immediate revenue you will be glad you set it up.
14. Be a content creator, not just a consumer.
Creating content builds authority, visibility, and trust. Consuming content only builds someone else’s business. This is one of the biggest mistakes I see people make when they are starting their business. If you are on social media, it should be as a creator, not a consumer.
15. Don’t chase shiny objects.
Stick with what works. Go an inch wide and a mile deep rather than spreading yourself too thin. I see way too many people think it is a good idea to try to build multiple different businesses at one time. It’s hard enough to build one business. Focus on one enterprise until it is working without you and then move towards the next project, if ever. Ideally, you will be able to sell your first business and then can start a second. But if you are trying to build multiple businesses at one time, you are playing a fool’s game. Podcaster John Lee Dumas used to say you need to FOCUS – “follow one course until success”. Remember this lesson and you will find success faster than if you are trying to multi-task on multiple businesses.
16. Automate whenever possible.
If you repeat a task more than a few times, find a way to systematize or automate it. My absolute favorite software program is Zapier, which can help you automate certain repeatable tasks. I love it so much that I won’t use any SAAS products that don’t integrate with Zapier.
Business Operations
If you build an amazing business, it will support you for years to come. But you can’t do it alone. As you develop a growth plan for your business, you should also focus on finding great people to help you reach your goals. I have found that the best use of my time over the years has been to spend dedicated time each week either working on my business or marketing my business – preferably a little of both. Here are a few tips that have made a huge impact on my bottom line, and have contributed tremendously to my business growth.
17. Keep business and personal finances separate.
Many people that are just getting started in business will use their business account as their personal checking account or vice versa. This is a huge mistake. Not only will it make your taxes impossible to prepare, but it also could lead to what is called “piercing the corporate veil”. Essentially, a potential creditor could use this co-mingling of finances as evidence to show that you and your business are one legal entity, thus opening up all your personal assets to garnishment or seizure if you get sued or audited.
18. Build a business that runs without you.
Many new entrepreneurs, especially service professionals, leave their corporate job to start a business doing the same thing they were previously doing for a paycheck. But now they are forced to work 2-3x as hard for half the pay. This is something that I wish more people knew when they started their own business. When you own a business, you are responsible for not only delivering your product or service, but you are also responsible for marketing, accounting, hiring/firing employees, and creating a vision for your business. Needless to say, it is a lot of work. If your business can’t survive without you in the office every day, you don’t really own a business — you own a job.
Alternatively, you should start the process of hiring staff and/or creating automation systems to deliver your products or services on day one of your new venture. This involves working ON your business as opposed to working IN it. And the sooner you can replace yourself with someone who can do your job for you, you will start to enjoy true freedom in your life.
19. Use technology wisely.
In this world of AI, it is so easy to just invest in a lot of fancy software that (you believe) will do your job for you. You can use software to create and post things to social media, create videos and podcasts, and even to respond to emails on your behalf. I recommend being judicious in your use of AI or any type of automation tool that replaces the human interaction. It will come across as unauthentic and disingenuous.
And if you don’t think people will notice, think again. I routinely skip articles on LinkedIn that I can tell were written by a bot. You can lose a lot of credibility and good will. So the lesson here is that you should use software to make your business more streamlined, but don’t use it to replace human interactions.
Software can save time and money, but it can’t replace human judgment or personal connection. Use it as a tool, not a crutch.
Final Thoughts
And now for my last and probably most important of my lessons learned in business.
20. Enjoy the Ride.
Looking back, the past 20 years have been full of mistakes, risks, wins, and surprises. Looking ahead, I know the next 20 will bring just as much change and opportunity. Although, if I’m being honest, I hope I’m not still working 20 years from now!
If you’re building your own business, I hope these lessons save you a little time, money, and stress. And remember: the goal isn’t just to build a business — it’s to build a life you love around that business model.
