Online Business Lessons from 14 Years of Entrepreneurship

In the spirit of my old ritual of making coffee and writing on Sundays, I decided to do a very long and very cathartic post on some of the most impactful online business lessons from over a decade of making money on the internet in various ways. Some of you have been around for my journey. You’ve seen a lot of ups and downs. Many of you are only now just finding me. So grab a cup of coffee or tea, sit back and enjoy the read.

It was November 2013. I was six months out of college, had just landed my first job in the middle of The Great Recession and wanted to be a writer. I had read The Art of Non Conformity by Chris Guillebeau that Summer and was fascinated by the idea that I could make money on my own on the internet. So I started a blog called Grad Meets World where I would write my coming into adulthood realizations.

That blog would turn into an eighr year career as a financial freelance writer. This was ironic because I was broke and knew nothing about money. I just wondered if there was a way for me to get paid to learn about money. First lesson, you can always learn knew skills and you don’t need a ton of degrees in a specific arena to profit from it. 

I ended up writing blogs for major financial institutions like Discover, Wells Fargo and Santander. I wrote blogs for FinTech companies and even had a column at Inc for a while. Oh, and I self-published an Amazon bestselling book called Make Money Your Honey and was hired as an influencer for campaigns for the likes of TransUnion and Capital One.

It was a fun time and I loved it. Until I realized two things:

• The way traditional finance talks and teaches about money is extremely limited and focused on lack. As a freelancer, I’d learned the importance of earning more money and having an abundance mindset, so I couldn’t continue getting down with the limiting shame-filled stuff anymore.

• Although I was doing well, I could not scale the business. Meaning, in order for me to make more money I would have needed to take on more clients which I did not have the time or the capacity for.

So In 2017, I started the process of creating my first successful course. I say successful because up until that point I’d tried just about everything to make money in some other way besides writing – affiliate marketing, an e-commerce store, an Etsy store, selling courses, selling a membership – and none were successful. I’d even attempted to sell coaching packages and was rejected 60 times in 30 days back in 2015.

But in the Summer of 2017 I struck gold when I created Persuade to Profit and made $10,000 in cash in two weeks just by telling people on my email list that I would teach them everything I had learned up until that point about running an online business. To date, our Persuade to Profit program has helped over 125 business owners improve the sales in their businesses and we’ve had nearly 3,000 people purchase our digital products.

Lesson two, you will fail a ton of times before you finally find something that works. This is normal and a part of the process. We’re constantly trying to avoid failure when in reality that’s what gives us the lessons we need in order to improve and finally make something work.

From 2017 to 2018, I did double-duty freelancing as well as selling Persuade to Profit. By the end of 2018, my course and coaching sales had far surpassed what I’d made writing and by 2019 I had a multiple six-figure business. From there I had what would turn into an obsession:

How the hell do I scale this thing?

From 2019 to today, I became obsessed with the concept of scaling, systems, processes and team building.  I wanted to build something that could run and make money without me.

I have to be honest and admit that it has been the most grueling and challenging three years of my life. While I’m beginning to see the fruits of my labor in the form or more passive income, I’ve had to go through a lot of frustration, mistakes and discomfort.

The end of 2021 and beginning of 2022 was the worst of it. My business was growing at a breakneck speed and it was clear that I did not yet have the systems and processes to fully support it. At the same time, my father was in and out of the hospital for eight months (he’s fine now) and I experienced what would be the worst burnout of my life.

The burnout would lead to eight months of terrible decisions, losing six-figures, debt, emotional purging, burning things down, losing my confidence and self-esteem and needing to completely rebuild my relationship with myself. I took a massive break in 2022 knowing that it would come at a giant financial cost, because I had to take care of myself first.

Lesson number three, you need to come first. I’d spent years not taking care of myself and making sure everyone else was okay. I spent years depriving myself in the name of building. Granted, the pandemic didn’t make matters any better because there was no way to reward myself during lockdown.

I also don’t regret it because, again, I’m now beginning to see the fruits of my labor. I also do believe everything happens for a reason and the burn out led to some of the greatest personal breakthroughs of my life.

Present Day…

And this is where we find ourselves today. At the end of 2022, doing my annual review with you here instead of doing it on the podcast. While this has been one of the worst financial years of my life, it has also been one of the best years for personal healing and reconnecting to the things I truly value. The problem is we only celebrate numerical success online but we rarely ever talk about personal goals or wins.

Now that I’ve re-emerged from the burnout fog I can look back and see exactly where I went wrong and what I will be doing differently moving forward. I’m detailing them here in an effort to help anyone who may find it useful.

Mistake #1: I think I lost sight of myself.

I was so focused on my goals – especially while we were all locked down at home and had nothing else to do – that I forgot what even made me happy. There is also so much freaking noise all the time about what you should and should not do that it’s maddening at times.

What I Learned: I was forced to go back to what made me happy during my break. The truth is it’s quite simple. Swimming, art, writing, reading good books, spending time with loved ones and knowing that I’m helping people with my work. That’s what I knew fourteen years ago and it’s what I’m rediscovering now.

What I’m Looking Forward To: As crazy as it sounds, it’s one of my worst financial years but I’m way happier and feel more connected to myself and others. I feel like I have a different relationship and foundation with myself despite all the challenges. I feel like I’m living again. Would I like to have more money and my debts paid off? Sure. And that will come. But for now I’m looking forward to reconnecting to the things I love again.

Mistake #2: My mindset work was not keeping up with my physical work.

I thought I’d done a ton of work on my mindset to receive success and abundance. What I did not count on and never expected was that my first six-figure month in the business would send me spiraling into a trauma response. My core wound – which I’d heard of the concept but never really understood – reared its ugly head.

Through therapy and working with experts, I learned that my nervous system was overloaded due to some ancestral trauma and childhood trauma I had never even considered. Basically, I did everything possible to get rid of the money because I was repeating ancestral patterns of fear. My family has suffered great trauma escaping an authoritarian communist dictatorship and I never noticed how I had picked up on their patterns until this moment. Basically, I was both afraid that something would come take the money from me (that’s what happened to my family) and I also felt immense amounts of guilt for being successful (my family has a pattern of survivor’s guilt). I couldn’t stand it so I self-sabotaged.

I also made things more difficult for myself to prove my worthiness of success due to some childhood trauma. I would spend months uncovering these things and emotionally purging them which as you can imagine was quite destructive to my every day life.

What I Learned: Unbeknownst to me, a good percentage of my business was built on trauma, fear and insecurity. I’m not an expert but I’ve had enough conversations with enough entrepreneurs to know that is the case for a lot of us. Many of my therapist friends have also commented to me just how common this is which leads me to believe since no one talks about it we’re all just suffering in silence.

What I want to do moving forward is focus on building a business based on love and service. I’m grateful for this experience because it has led to so much healing within myself and also my family and personal relationships. I also now have better tools for managing my anxiety.

What I’m Looking Forward To: I look forward to a business where the model is love not fear, abundance not scarcity, and service not transaction.

Mistake #3: I had the right ideas, but I tried to execute too many of them at once and at the wrong time.

I was growing way too fast in the business. So fast that the systems and team I had could not keep up. I also over-hired thanks to some terrible advice I received and was super distracted with way too much on my plate. This mixed with my father’s health issues and a full-blown trauma response were a recipe for disaster.

What I Learned: Slow down. You don’t need to do everything all at once. It’s important to have solid foundations in place. Sometimes the slowing down is necessary so that when you do speed up you can sustain it. I also learned that at least I made all the mistakes in one shot so I got them over with haha.

Mistake #4: Doing too much myself.

Prior to 2022 I thought I was pretty good at asking for help. I was dead ass wrong. The truth is I was still doing too much, still holding in too much emotionally and still not really very good at receiving help and support from others. This was a part of what led to burnout. I also realized this is actually a learned pattern.

This year forced me into asking for help in spite of my pride. It forced me to rely more on others. It forced me to seek professional support for my mental health. It forced me to ask for favors.

What I Learned: The idea of rugged individualism is nonsense. No one can get through life alone. This is actually one of the reasons that I hate the popular narrative online that you can run businesses without talking to people. You can’t. Literally everything is a relationship. Alternatively, I’ve also looked to more automation and systems to better support me as well. I also learned I don’t have to prove my worthiness of being helped. I get to receive help because I can. Previously I thought I had to do something for it to prove my worthiness.

What I’m Looking Forward To: I’ve really enjoyed leaning back more and letting other people help me. It has shown up in different ways like men in my personal life wanting to solve my problems, my family really stepping up and showing more emotional support than ever (this is not typical in my family so its a big deal), strangers giving me free stuff, joint venture partners sending us business, etc. I’ve also enjoyed watching the systems I slaved over starting to work efficiently.

Mistake #5: My priorities were fucked up.

Since 2019 I’ve had pretty much one priority: build this business. That became even more so during the pandemic when again I had literally nothing else to do. In my brain, I thought that if I wanted to show up for relationships then I basically needed a business that ran on autopilot. Truth be told I have no idea where I got this from but it was the story I was operating under and it was very wrong.

What I Learned: Ironically, I created quite a financial mess and my personal relationships are better than ever so clearly I was very wrong about that one. I’m prioritizing relationships moving forward: with Source, with myself, and with others moving forward. In fact, my new company motto is “Make Talking to People Cool Again” because it really is about prioritizing human relationships.

Mistake #6: Thinking the way other people run businesses is the way I want to run a business.

A couple of years ago I started studying much bigger companies and what they were doing in order so that I could model it in my own business. A lot of the advice has been incredibly useful and I’ve applied it. In fact, I’m eternally grateful for the skills, strategies, concepts and ideas. Those alone are worth more than any amount of money I could have. However, what I also realized is I don’t necessarily want to run a business the same way they do.

What I Learned: Do you boo. And then accept what yourself for it. I see a lot of people online insisting they must do business in this one specific way. This leads them to chase trends and generally be exhausted and second guessing themselves. In reality, you need to align with what works for you in order for the abundance to flow.

What I’m Looking Forward: Getting back to running a business I love.

Mistake #7: Sometimes you need to burn stuff down and restructure.

I needed to do some major restructuring in my business in 2022. I spent more than half the year not really being satisfied with our offers not out of perfectionism but because I had evolved and changed and my business was not in alignment with the evolution. The thing was it was much harder to restructure than normal because I had a lot of resistance to it. I thought it had to be all or nothing until I found a rather happy medium.

What I learned: For example, I needed to let go of teaching how to create offers live. It was no longer in alignment and I would have been competing with some potential partners rather than collaborating and growing each other’s businesses. Rather than throwing out the baby with the bath water which is what I thought I had to do – I made it available for purchase on demand instead.

I also got rid of stuff. I stopped doing YouTube videos and started sticking to livestreams instead. Less work still the same impact. I stopped posting on Instagram and TikTok because I don’t have the capacity. I put the podcast on hiatus for the same reason. I basically got rid of stuff that wasn’t in alignment with where I’m going.

What I’m Looking Forward To: More passive income sales (already happening!) and having more options for people to work with us.

Mistake #8: Some things take longer than you’d like.

Building out systems and training team has taken way way way longer than I would have liked. In fact, the team thing is still a work in progress.

Lesson Learned: Don’t expect everything to happen quickly even if you’re used to things happening quickly. Patience is a virtue.

What I’m Looking Forward To: Someday having a solid team that really supports the work. Scaling the front end of the business and letting the systems do their thing.

Mistake #9:  Taking too long to cut expenses.

I ruthlessly cut stuff out of the business in 2022. If we weren’t using it and wasn’t generating ROI, it was gone. Period. The problem was I should be doing this on a monthly basis but didn’t because I was so distracted by other things so stuff piled up which partially led to the debt.

Lesson Learned: Being resourceful is okay and not the same as being cheap. Getting rid of stuff that is not giving you the proper energetic return is necessary.

What I’m Looking Forward To: A simplified business. Getting back to some of the useful stuff I learned from my finance days.

Mistake #10: Waiting too long to pick up the phone again.

Because I took so much time to build systems and train team, my sales game slipped big time. My idea was to get the stuff done and then run like a gazelle on the front end. It makes logical sense except for the part where I miscalculated how much work it would be and how long it would take. So another lesson in pacing myself.

Lesson Learned: Pace yourself when you are in transition rather than trying to get the transition over with.

What I’m Looking Forward To: Selling again. I love sales and I love talking to people. Last Monday I was making calls and generated $2600 in sales I may not have otherwise generated. I’m looking forward to getting back to basics.

Mistake #11: Hiding parts of myself.

I’ve been hiding parts of myself for years. While I was developing the analytical side of myself that now geeks out over marketing, sales, data and psychology I was surpressing the part of me that believes in God, energy and faith. As such, I mistakenly assumed that my business was all on me and I did not have celestial support. Another reason for the burnout.

I’ve also been afraid to show that side of myself because so many people have bastardized these concepts on the internet and have hurt a lot of people in their wake. I never want to do that.

But its become clear to me that I cannot hide parts of myself and expect to be abundant. That’s not how it works.

Lesson Learned: God first. Always. My intuition knows what’s best and removing it from the equation – even accidentally – never works out.

What I’m Looking Forward To: Sharing more about my faith and spiritual concepts with my community.

Final Thoughts

If you made it this far then congratulations and thank you! I hope this post served you as we enter a new year. My prayer is my story helps you on your journey no matter what stage of it you may be in.