My million dollar mistake


Artist Odyssey

Hello World Changer!

I walk into a meeting room in Miami with two other people from our team, feeling anxious but hopeful.

We’re taking a moment out of hosting our coach retreat to conduct the final interview for a tech lead who we are counting on to fix what may be the biggest and most expensive mistake we have ever made.

We have been paying a large tech team in Ukraine every month to develop an app called ArtSocial that will host art contests, all of our content, our programs and instructional videos, and a social feed.

They have been tasked to build out a coaching and mentoring platform as well as an artwork selling platform within it. We have plans for LIVE auctions, virtual commissions, virtual studios where artists can come together to create and connect, and integrating AI artist managers trained to help artists grow their business.

Developing this platform has been a huge step for us, full of excitement and vision, but it’s also a large and uncertain investment. And at this point, we are stuck.

We have been stalled out for almost a year with very little improvements or progress on the app. Nothing is moving. There are no new updates, and we cannot get answers from our team.

The lead on ArtSocial just keeps telling us they are building something very strong and solid, that it takes time, and that the new innovations are coming next quarter. But next quarter has passed us by for at least a year now, so we are changing things.

Hiring a new tech lead in the project who can go in and do a deep dive to see what is actually happening will really help us gain understanding to know how to move forward. He will also check on the team, audit its efficiency, and make sure everyone is pulling their weight.

A Whole New Landscape

Over the last few years, I learned a ton about development and how to build a digital platform. I never thought I would be the CEO of such an endeavor.

I’m an artist! Sitting in meetings with developers and programmers and talking about various sprints to build all kinds of intricate pieces of the platform is far away from my comfort zone of dealing with artists beating resistance, overcoming self doubt, dealing with perfectionism, or trying to create more contrast or achieve a great color story within their piece.

Getting into development was never my vision or intention, but 2020 really changed our business. We used to host our mentoring and coaching on Facebook groups. It was easy. Everyone had a Facebook account anyway, and then we would invite them into a closed group where we could easily coach and mentor our students.

It worked well until the Covid restrictions began. Halfway into 2020, we started hearing from some of our students that they were deplatformed from Facebook and, because they lost access to their accounts, had to cancel their coaching and mentoring.

Over the next several months, we lost a significant number of students from coaching. Customer service was riddled with endless complaints and requests for some other way to receive coaching.

We migrated to Telegram, but it was confusing and difficult. Many students who were happy with Facebook and didn't get kicked off, didn't want to migrate, while the other half, who couldn't use their Facebook account, welcomed the change.

This is when we decided to create our own platform so that no social media company could control our business or dictate our income. It opened the door for many innovative ideas and ways we knew we could help artists.

Because one of our partners was Ukrainian and knew a lot of techie people in Ukraine, we could see that we could easily build a development team at a third of the price of a US company. Our heads grew large with the idea of becoming the first social media just for artists. So we bought the domain ArtSocial and jumped off the tech cliff.

Crisis and Connection

It was exciting and new and fun. My role was to think up features that would solve artists’ problems. It felt empowering and visionary. I loved it.

I started to live in a reality of building something truly unique for artists. I started seeing the vision God gave me at 19 years old begin to morph from a 1,000-acre plot of land into a digital community for artists. I even began to second guess the vision entirely.

I thought, “Elli, you didn’t know what social media was in 1992. You just saw a metaphor of a digital community. The land development was actually an online platform you’re meant to develop.”

So we forged headlong into our endeavor. My three other partners and I rolled up our sleeves and invested thousands and thousands each month. We launched ArtSocial in January of 2022 and moved all of our content there for students to take the Mastery Program, engage in Art Club, and build their profiles. It was an exciting moment to see all of the investment and fruits of our labor actually become something artists could use.

But then, just a month later, the Ukrainian war broke out. Our development team was dodging bombs and running into bomb shelters between working and building the platform. We had to buy generators so that their internet wouldn’t be interrupted in the middle of coding something.

The team told us again and again how grateful they were for the employment and purpose. This was particularly difficult because naturally after a launch there are bugs to work out, and our team was not always available. The lead architect of the platform fled to Canada and was able to get into a stable environment by April.

In many ways, I felt like our Ukrainian team were heroes living in bizarre and tumultuous times, still dedicated to helping artists. They told us many times in the meetings that seeing the activity online and that artists were actually using the platform meant the world to them. It gave them something to look forward to each day.

It was greatly gratifying to see the efforts in real time. They said most development projects stay buried in R&D mode indefinitely.

As a team, we felt like we were a part of something bigger than ourselves. It gave us something concrete that felt like the beginnings of a movement. We were proud of what we were building.

Searching for Answers

But over the next year, things began to stagnate and slow down. We saw money burn each month with not much to show for it. The platform was glitchy, and customer service spent a lot of their time helping artists with work-arounds.

My partner and I began to research other platforms and saw that many changes had happened over the last few years while our heads had been down, buried in our own project. Mighty Networks built white-labeled platforms that you could fashion into whatever you wanted, and they did all the developing. It cost a fraction of what we were spending.

But we had gone too far. We had already spent over a million dollars creating ArtSocial, and we couldn't pull the plug. We couldn't imagine firing our Ukrainian team in the middle of a war. The thought was heartbreaking.

So we pressed on. We endeavored to work smarter, tighter, with less waste. We organized our new releases in quarterly sprints. But after several months and many missed deadlines, it just wasn't happening.

I didn't understand the intricacies of the tech or read code or understand the backend. I could only listen to what the leads were saying and hope they knew what they were doing.

I knew I was in a difficult position to spend my money on something I knew nothing about and couldn’t actually see for myself if it was done right. I finally had to admit I needed real help.

My hope rested in an English-speaking American tech lead who I hired to dive in and report to me what he found. He had 90 days to give me a full report of where we were weak, broken, or dysfunctional; who were the A players, B players and C players; what needed to be done to get things on track; and how much would it cost.

The Verdict

In December of 2022, I was in the Tampa airport heading to the UK for business when I got the call from our new tech lead. Jake and Dimitra were with me.

“Hi Elli, this Dakota. I have created a full report of everything you have been looking for. It’s all laid out with an overview, the details, and what I think we should do next.”

“Wow! Okay, I look forward to reading it. Can you give me a brief rundown here on the phone? Are we looking good? Bad? Somewhere in-between?” I ask.

“It’s kind of bad. I’m gonna say, it’s really bad,” says Dakota with a bit of a shaky voice.

“Oh, crap! That's not what I was hoping to hear. Okay, tell me, what’s the bottom line?” I ask him.

“So the good news is your lead architect, Andre’, is great. He built a solid backend. He’s a definite keeper. However, your entire frontend was built in a language that is now obsolete, so without updates it will just get glitchier and glitchier to the point that you won't even be able to use it. So we have to immediately rebuild the frontend in a new language, and it's a race for time to get it done before the current gets too glitchy to use.

“We could hire more people, or try with what we have. I don't feel as confident with the frontend programmers because they are the ones who chose this language. But it will take time to hire new people, and we don't have time. My best guess is it will take six months and about $600,000 to fix this. Then we can move forward with the new features you want.”

Bad news delivered.

I was shocked and crushed. My whole world came crashing down right there in the Tampa airport. I hung up with Dakota and told Jake and Dimitra the bad news.

We spent the next few hours sifting through our options. Eventually, we unilaterally all came to the same conclusion: we had to scrap it. We had no other logical choice.

We realized that technology was changing faster than we could keep up. Our little team wasn't efficient or savvy enough to stay current. If we really wanted to compete, we would need all A players who knew how to use AI and made all the right choices. We would need a real and true tech lead that was adept and at the forefront of what is coming.

The Shiny Object Trap

We realized no matter how good this felt and how exciting it was, we are not a tech company. We are artists. We create content. We teach artists how to paint. YouTube and Instagram is our lane, not software and platform development. If we took the fortune we spent every month on tech and spent it on production of content, we would be seeing a much bigger return on our investment.

I felt terrible that I had allowed us to get seduced. We chased after the sexy woman in the red dress rather than building what we know is our true calling. It happened so easily without any of us seeing it. But now that we saw it, it was impossible to unsee.

Our next moves would be to dismantle ArtSocial, shift into Mighty Networks, and double down on content. This would be a lengthy and expensive transition, but we had no choice. It would be painful to slowly let go of all of the Ukrainians, especially Andre’. It would mean buying out a partner—also very expensive. It would mean a disruption in our students’ flow and possibly complaints.

This would be by far my biggest failure yet.

Yes, this failure cost me more than any other in the past. This failure would affect a ton of people. Poor Dakota audited himself right out of a job. I had failed on multiple levels. But the failure I was most upset about, most shook with, was that I left my calling.

I was dazzled by a new shiny object. I forgot what my destiny was. I took the dream, clear and true, that God gave me and twisted it into something unrecognizable. The bright green acres he showed me in a vision at 19 are still those acres. They are not a digital planet, as exciting as that was to believe.

Even as I write this, I reaffirm my commitment to the true vision and dream God gave me and decide to only surround myself with those who remind me of that dream and share that vision. I will not partner again with anyone who will lead me away from the vision or sit complacent and comfortable, unable to challenge me in my bad decisions.

It is easy to wander off, but my heart longs to stay faithful and focused, to see the real vision come to fruition. I decide to keep my eyes set on that vision, and to only surround myself with steadfast keepers of the dream.

I encourage you to stay true to your own dream. Don’t shrink it to fit your reality or your unbelief, and don’t be dazzled by another idea and slowly morph your vision into it. Whatever dream came to you pure and true, hold onto it tightly and never let it go.

What dream have you had to fight to stay faithful to, even when distractions and opportunities tried to pull you away from it?

▶️ LIVE on YouTube

If you’ve painted dozens of portraits but none of them seem to sell, I want to show you why.

Most artists think the problem is their proportions, anatomy, or color mixing. But in my experience, that’s usually not the real issue at all.

Today at 4pm ET, I'm hosting a free live workshop where I’ll break down the real reason so many portraits don't sell.

I’ll show you the four symptoms I see over and over again in portraits that don’t connect and give you the one question that can completely change the way you approach portrait painting.

Going LIVE in:

Count down to 2026-05-13T20:00:00.000Z

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Elli Milan

Visionary artist, author, educator, inspirational speaker, and founding owner of Milan Art. Revolutionizing how art is sold and artists are taught. Excellence in art without elitism.

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