2022 Reflection - Lessons Building a Software Agency, Burn Out, and Moving to Argentina

Hey friend,

Glad you are here! You probably subscribed to an old newsletter post of mine and now seeing this. This is a long overdue reflection on my past year and hope that it inspires obedience + risk-taking in whatever you choose to do in life.

The Highlights

• I was tired of the lack of growth in my 9-5 desk job and wanted to ship products fast and make a positive impact

• With zero experience, I stumbled into making high six figures in rev my first year

• I built a dream team and traveled across America for conferences, deals, and fun off-sites

• I became a more self-aware entrepreneur and gained renewed confidence in who I am

• I learned that showing up is a powerful force

• I surrendered the opportunity to make a ton of money and choose a different road

• Moved to Argentina 🇦🇷 to build my next thing

Here is a reflection of what I learned about building a business this past year.

My close friend Jon and I built a software agency that worked on building apps that infected the world with more joy, hope, and peace. The revenue model was quite intuitive you get paid based on fulfilling building apps for customers. Our vision was to help non-profits and mission-driven organizations that weren’t the best at technology execute their products with limited resources.

I had just left my first product gig out of school. I had worked there for 3 years and decided I needed a bit of a change.

So there I was 25 with absolutely zero idea of how to truly operate a business.

One of the early startup killers is too much information. There were about 20 different frameworks from different books we had read and loved on starting a business.

The issue is that now that anytime you decide to take that first step you think you aren’t ready cause you have constructed your baseline of what you think is necessary to start something.

Lesson 1:

• Just start and get skin in the game

• If we would’ve spent less time on perfecting our 5-10 year vision, logo, networking events, story brand, revenue model

• Often you don’t even know how your year one is going to go

• It turns out that none of that stuff is static and it doesn’t compound your ability to build products for people

So we just started taking on customer work as we were trying to figure out who we were and this is normal. But make sure to not jerk around your customer on all your pivots they are looking for you to be their guide up the mountain to building SaaS. Stick to one product framework let it actually fail and then reassess with your customers.

Lesson 2:

• Communicate Risks + Progress Early and Often → Truth reveals itself

• This might seem obvious but when you are just starting you don’t want anything to look bad. It's like when you aren’t fully vulnerable with someone when you are dating but when you start living together you can’t hide who you are

• Fight to resist this ASAP as their guide you must let people in on the difficulties you will gain mastery on bad news delivery

This is important cause when you just ship every week and do these lovely shows and tells. The week or nights when your team gets hit hard with challenges you are going to be left holding the bag trying to explain to your customer why you weren’t able to make progress this week.

Building a product is chaotic so let your customers feel the pain and this will help be more embedded on the journey to building something that matters.

Your team is capable of so much good! Oftentimes, you as a founder are the problem. I know the adage hire slow, fire fast. Let’s pretend you have an all-star team of smart people that want to help. Ego however is your biggest enemy.

I took ownership of slide decks, strategy, and overall communication. I had crafted a process and claimed I had the best way to deliver on that each week. I had become tunnel-visioned.

I did it alone every week. Failed at delegating it and it robbed me of a lot of joy.

I often sat in a room alone after hours strategizing how we were to execute a certain body of work or product increment.

Lesson 3:

• Don’t overthink delegation and let your team in on the hard things

• There is a reason you have sacrificed pay for yourself and stayed up late at night. You haven’t come this far.

• Trust me when I say that your ego will kill a business faster than most things

• Let people learn and grow — delegation is a great way for people to grow in a new competency and open the door for innovation in your company

The first 3 months of the business were extremely challenging. We needed to hire a designer and a marketer and someone to do operations. So we did. In the midst of that, our burn quickly increased and our income didn’t.

As a naive founder, I took on a second job to keep the company afloat and forfeited pay. It worked, let me rephrase that it showed me that I am not invincible.

I ended up having a panic and anxiety attack because I had $3000 in our business bank account and we had to make payroll by the end of the month. Payroll was much more than $3000 and that was a looming nightmare.

It was a scary time and despite all my efforts, nothing gained traction in terms of trying to land someone else as a customer.

Just in the nick of time, we ended up getting super lucky that our existing customer wanted to continue working with us and agreed to a bigger project!

Lesson 4:

• Show Up

• We wanted to quit. I am so glad I didn’t at this point cause we ended up experiencing big growth after this inflection point

It was at this point we finally had enough money to get a desk in our co-working office.

It was amazing we had a paper sign taped to the desk. That is bootstrapped life.

We started to be surrounded by other successful founders. For example, one of our customers was also a former founder who had many exits. In our co-working office, other agencies started renting space and hearing about their cool wins.

That bred a lot of envy especially since you are at a different point in the journey but want that lifestyle they had with their fancy offices and big-name customers.

To catch up in a race that wasn’t ours to run.

We tried taking on customers for website optimization, automated help centers, graphic design, and growth hacking. This was a great way to sample what we did like and what we didn’t. At the same time, it was a good way for customers to identify what we were good at versus not.

I am fortunate to have a customer that dared to say you guys aren’t the best in all the areas you claim you are and are better at building mobile apps.

Lesson 5:

• Focus and stop comparing yourself

• If you are comparing yourself to someone that has decades on you. You have already lost.

Our team pivoted and adopted a product framework that we had been given by our customer who turned mentor. This was an extremely rare situation where the customer turned guru and we had turned mentees. He was an absolute super fan of us and without him, we wouldn’t have been able to navigate this season of focus.

A few weeks later we were introduced to a non-profit in the Bay Area that completely changed the trajectory of our business. We always dreamed of establishing a long-term relationship with someone for a social impact mobile app.

Lesson 6:

• Be Too Hot and Too Kind

• We sent personal Looms showing them how the sausage was made. We didn’t hide how we priced, how we wanted to tackle the project, or the proposed tech stack and we never delayed our response by more than 2 hours.

After a few days, we received the email we had always dreamed of. We got it!

We flew to the Bay as a team. Did an in-person design studio and began cranking on an app that helped foster families. It was totally unlike anything I had ever had the chance to be a part of.

You know that feeling of being in a hackathon and everything is just gaining momentum?

A few weeks later as we continued to deliver on many different deliverables and coordinated our team from serving just a handful of customers. I now had to learn how to balance and provide attention to every one of my customers.

It was a bit rocky and we even got complaints from one of our customers about how it felt like we weren’t as attentive. Again, all growing pains but when your customer begins to say anything along those lines. It's better to be proactive about expectations moving forward in terms of the service as you scale.

The months of shipping great work, discovery, and sharpening our sword continued. I grew immensely as a product thinker more than any normal job would do in such a short time.

Eventually, we got offered to be acquired-hired and merge our agency with another. This was a tempting moment cause it would solve many financial burdens we had carried and place a constraint on our vision for us.

We would have to align our focus to serve the mission and vision of our acquirer.

The thing with this that I came to learn was if all your business partners aren’t bought in. Then acquisitions are just distractions. Lots of lawyers and lots of time in due diligence, and playing the game.

If you aren’t all bought in you are playing a game you can’t win. Unless you all want to sell and put up with a distraction. Don’t do it.

Lesson 7:

• Optionality

• I think at this point I think we were on the verge of being distressed. We had assembled a kick-ass culture and team that could deliver on software projects.

• However, none of us had taken accountability to build a healthy pipeline of new opportunities

In other news, revenue was coming in but we had made the mistake of scaling way too quickly.

What this led to was being dependent on one of our customers far too greatly. If they were to ever pull the plug the business would be in a lot of trouble.

As we continued through the iterating of many things we finished our first year in the business. It was a year with a lot to celebrate.

We had a lot to celebrate at this point.

I was proud of my team and myself.

A few months later as projects got more complex we started to see how much toll some team members had trying to keep everything together. One of my co-founders was the only engineer for a bit and that was brutal.

I think for a long time I let people on my team who shared my values but lacked the skills stay in roles they weren’t fit for. I was clouded by leaning heavily on values that they would eventually learn the skills. The reality of it is anyone can learn anything but if they don’t have the margin to learn that skill they aren’t just going to learn it.

A harsh truth is that certain team members get you to a certain stage and others hold you back.

I was spending too much time trying to make sure people were happy with everything and failed to strategically transition my people within or out of the company. Don’t keep friends around for the sake of keeping friends around in the business it can hurt the profitability of projects.

Lesson 8:

• Distinguish between building a family or business

• As a leader, your job is to steward your people and speak truth into their lives. Also, challenge them to live a bigger story and make sure they get paid well.

• I should’ve encouraged leaves of absence for people to reflect if they want to do this and lay out very clearly what it would take to still be a member of the team

Ultimately, some leadership conversations that followed were difficult. I had personally become burnt out from trying to patch all the holes within the business. I told my co-founders that I was going to leave the company because I just didn’t have peace about the direction we were headed.

That was a big moment. One none of us saw coming. I think combined with all the panic attacks it had dawned on me that I was not in a healthy spot.

I had a trip planned to Argentina to expand our existing development team in Boulder and California. We had already been near-shoring engineers and as the trip neared it felt like the perfect next step in scaling our business to the first major milestone in revenue.

So I sold everything I had and embarked on a trip to Argentina. During my final weeks before I was to go to Argentina my team at an offsite had asked if I would consider returning and being CEO.

This was something that I always wanted. My team also recognized the direction I could take the company.

Luck and God’s favor are some ingredients for success for many entrepreneurs and certainly mine.

Yes, there is hard work that comes with starting your own thing but we must recognize all the last-minute referrals, friends turned advisors, investors making dream intros, and hitting milestones in the knick of time.

I spent a month in Argentina not checking email, not checking Slack, not joining standup. That was extremely hard, especially being so attached to the products and team I invested in. Just actually spending time with myself and who I was.

My brother even came to spend some time with me :)

Lesson 9:

• You are being led

• Often God will call you to do things that don’t make sense. Like forfeit your 6-figure dream salary to start something

• Your mistakes are already being restored and don’t be too hard on yourself

Living in Argentina was a huge culture shock. If you haven’t ever been it's a beautiful country and I highly recommend visiting.

After many many weeks of prayer and journaling alone. I heard God saying it's no longer your burden to carry this company and as much as I want you to be CEO. I don’t want you to risk Becoming a King too early.

One of my favorite quotes is from a book called Becoming a King by Morgan Snyder actually:

“We can offer only who we have become; we do not provide what we do not possess”

So I turned down the offer to be CEO or return as a team member.

My former partners and customers have been incredibly supportive and I am super lucky. There was lots of imposter syndrome and addiction to the feeling of wanting to be accepted during building this first business.

I’ve been in Argentina for 3 months now walking with God.

This season has been full of a lot of internal wrestling of my soul to find peace. I surrendered the opportunity to make the most money I would ever make and choose a different road.

The best is yet to come and I am just getting started.

Instagram: @whereisamar