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Starting an investment group with friends sounds like a brilliant idea on paper. Combine your knowledge, share ideas, hold each other accountable, and grow your money together — what could possibly go wrong?
A while back, I had that exact idea. I envisioned a small, focused group of people who genuinely wanted to learn how to invest, exchange insights, and improve our financial literacy together. The concept was simple: meet a couple of times a month (later reduced to once a month for about two hours) via video call to discuss everything from stocks and ETFs to long-term strategies and personal finance habits.
At first, it was incredible. Everyone was engaged, curious, and eager to participate. We had lively discussions about market trends, new investing tools, and our personal goals. It was refreshing to be around people who wanted to grow financially. But as with many great ideas, reality eventually kicked in — and things didn’t go as planned.
The Excitement Phase
When I first pitched the idea, my friends were enthusiastic. We created a group chat, set a meeting schedule, and even made a shared spreadsheet to track what topics we’d cover each week. Everyone had something to contribute — one person was into real estate investing, another was learning about dividend stocks, and someone else was experimenting with crypto.
During our first few meetings, the energy was amazing. People were prepared, curious, and excited to share what they learned. It was a nice mix of collaboration and accountability. I remember thinking, This is it — this is how we’re all going to level up financially together.
I spent hours preparing for each session — reading articles, watching videos, researching companies, and finding new investing strategies. I wanted to make sure every discussion added value for everyone involved. It felt productive and purposeful.
But enthusiasm has a short shelf life when commitment is low.
When the Cracks Started to Show
After a few months, things started to fall apart. At first, it was subtle. Someone would show up late to the call. Another person would skip a meeting, promising to “catch up next time.” Then, one day, one of the members admitted they didn’t do the “assignment” — meaning they hadn’t researched the topic they were supposed to present. Instead of contributing, they used the meeting time to do the work they should’ve done before.
That was the first red flag.
It’s hard to have a productive conversation when not everyone is equally invested. When people start showing up unprepared, the dynamic shifts — the energy drains from the group, and the momentum dies down.
Then, there was the over-questioner. Every group seems to have one — the person who dominates the conversation, often unintentionally, by asking endless questions that go in circles. Ours fixated on one particular topic: “How do you know when to sell before the stock drops?”
It’s a fair question — every investor wrestles with timing. But no one knew the answer and the person kept on followed up with ten more “what if” questions that no one really had an answer to. It got to the point where the group couldn’t move on to any other topic because we were stuck trying to satisfy an unanswerable curiosity.
Eventually, the meetings became less about learning and more about trying to manage people’s attention and egos.
Priorities Change When Motivation Fades
Soon after, the excuses started rolling in.
“I can’t make it this week — I am going somewhere with my gf tomorrow.”
“The basketball game is on.”
And just like that, what started as a focused group of aspiring investors turned into a ghost town. People’s motivation to learn about investing faded as soon as something more entertaining came along.
It made me realize something: not everyone has the same drive or priorities. What’s exciting to one person might feel like homework to another.
To me, the idea of spending two hours a month talking about investments and building wealth was a no-brainer — an investment in my future. To others, it felt like an obligation competing with their leisure time.
After the one meeting that no one showed up because they had other obligation was the final straw. The enthusiasm just wasn’t there anymore. It was like trying to restart a fire that had already gone cold.
The Warning I Ignored
One of the members said something early on that I brushed off at the time.
He said, “If anything goes wrong with this group, you might lose friends over it. I started a group like this before, and it didn’t end well.”
I remember thinking, That won’t happen here. We’re different. We all want the same thing.
But he was right.
When money, opinions, and personal accountability mix — things can get complicated. Some people take feedback personally. Even though no one was trying to offend anyone, the small frustrations — lateness, disorganization, overtalking — began to chip away at the sense of teamwork we once had.
By the time the group unofficially dissolved, it was awkward to even bring up the topic of investing. What used to be a shared interest had become a reminder of a failed collaboration.
Out of the four of us, I only still talk to one — a friend I’ve known since 2017 from work. The rest were mutual friends, and those connections faded once the group ended. Not because of a big argument, but because the shared purpose that once brought us together no longer existed.
Lessons Learned from a Failed Investment Group
Looking back, I don’t regret starting that group. It was a valuable learning experience, not just about investing, but about leadership, motivation, and human nature. Here are the biggest lessons I took away:
1. Not Everyone Shares Your Level of Motivation
Just because you’re passionate about something doesn’t mean others will match your energy. Some people like the idea of learning or investing, but not the work that comes with it. You can’t teach motivation — it has to come from within.
2. Accountability Only Works If Everyone Agrees to It
A group like this thrives on accountability. But if members don’t follow through, the system breaks. It’s frustrating to carry the weight for people who don’t put in the same effort. In hindsight, I should’ve set clearer expectations — or gently removed people who consistently didn’t contribute.
3. Too Many Opinions Can Derail Progress
There’s a fine line between discussion and debate. When one person dominates with questions or arguments, it can stifle others from sharing. A good group needs balance — structure, moderation, and time limits to keep conversations productive.
4. Money Topics Can Strain Relationships
Talking about money — even hypothetically — brings out strong emotions. Some people get defensive, others competitive, and a few might take things personally. Mixing friendship and finance requires emotional maturity that not everyone has.
5. You Can’t Force Growth
You can create opportunities for people to learn, but you can’t make them take it seriously. The best you can do is lead by example and hope it inspires someone along the way.
What I Would Do Differently Next Time
If I were to start another group like this, I’d treat it less like a casual hangout and more like a structured club. I’d:
- Set a clear purpose and rules of engagement from day one.
- Limit meetings to a strict 60 minutes.
- Assign specific, measurable goals for each session (e.g., “Each person presents one stock and why they like it”).
- Keep the group small — ideally three committed members, not more.
- Rotate leadership so everyone takes ownership.
- End meetings with action items — even something simple like reading one article or watching one video before the next session.
And most importantly, I’d choose people based not just on friendship, but on their mindset. Being friends doesn’t automatically mean being compatible business or learning partners.
The Bigger Lesson: Growth Is Often a Solo Journey
The biggest takeaway from all of this is that personal growth — especially financial growth — is often a solo journey. You can share the path for a while, but ultimately, everyone walks at their own pace.
I used to think that surrounding myself with friends who said they wanted to learn about investing would help all of us succeed together. But what I learned is that you can’t depend on others to fuel your momentum. If they slow down, you can either wait or keep moving forward.
I chose to keep moving forward.
Even though the group didn’t last, the experience reinforced my commitment to self-education. I continued reading about investing, exploring new strategies, and growing my portfolio — on my own terms.
Sure, I lost a few connections along the way, but I gained clarity about what truly matters: consistency, discipline, and mindset.
Final Thoughts
Starting an investment group with friends taught me more than just financial lessons — it taught me about human behavior, leadership, and the importance of surrounding yourself with people who match your ambition.
Not everyone wants to grow the way you do. Some people are comfortable staying where they are, and that’s okay. What matters is recognizing who’s genuinely committed and who’s just along for the ride.
If you’re thinking of starting a similar group, go for it — but do it with realistic expectations. Be prepared for enthusiasm to fade, for people to drop off, and for priorities to shift. And when that happens, don’t take it personally.
Because in the end, the journey to financial success isn’t about who starts with you — it’s about who stays consistent when things get tough.
And sometimes, the best investment you can make is in yourself.
