Rivr Conversations

Inspired by Brent Drever’s Rivr Notes newsletter, this episode explores the humbling story behind “My Worst Best Investment.” It’s a tale of high hopes, fast decisions, and a startup that was supposed to be the next big thing—but wasn’t. We’ll talk about what happens when you chase shortcuts, the costly lessons that come from getting it wrong, and why those missteps might just be the best investments in disguise. It’s a conversation about patience, persistence, and the power of playing the long game.

View the Rivr Notes for this Episode > https://onrivr.com/rivr-notes/my-worst-best-investment/

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What is Rivr Conversations?

Rivr Conversations is a podcast inspired by Brent Drever’s Rivr Notes—a newsletter that sparks reflection and offers practical insight. In each short episode, expert Rivr Guides unpack the latest note, exploring themes of leadership, performance, and wellness. If you’re seeking grounded wisdom in under 20 minutes, you’re in the right place.

Andy:

Today's conversation is about something we all chase, quick wins and easy answers, and the hard earned lessons that come when those shortcuts don't pay off. It's inspired by Brent's Rivr Notes post, My Worst Best Investment. We'll unpack the story of a sure thing that turned into a financial flop, and how that failure became one of the most valuable lessons in patience, persistence, and playing the long game. Whether you're building a business, managing a team, or just trying to make better choices, this one's about the wisdom that only comes from getting it wrong and growing through it. I'm Andy, your Rivr Conversations host, and part of the AI team working alongside Brent, the creator of Rivr Notes and this podcast.

Andy:

Rivr Conversations is an extension of Brent's popular weekly newsletter, Rivr Notes. Each week, two of our expert Rivr Guides sit down to reflect on the latest note, sharing insights, takeaways, and stories that explore leadership, performance, and wellness in a grounded, thoughtful way. With that in mind, let's step into the river and hear what our guides uncovered in this week's journey.

Lena:

Hello everyone, I'm looking forward to today's conversation. Welcome to the deep dive. Today we're, looking into a recent issue of Brent's Rivr Notes newsletter. He shared a really well, a pretty personal story in it about an investment he made early on.

Reed:

Yeah. That one caught my eye too. What's interesting is how he takes this, you know, relatable situation, an investment that went south, and uses it to explore some really core ideas about making decisions, thinking long term. And those ideas tie right back into those themes we often see in Rivr Notes leadership, performance, even, wellness.

Lena:

Absolutely. And for this deep dive, our mission isn't just rehashing the bad investment part. It's really to dig into the lessons learned. What can we pull out about assessing risk, making choices, and frankly, what it takes to find real success even from something that looks like a failure.

Reed:

So the story kicks off with what seemed like, well, the perfect opportunity, a golden ticket situation as he calls it. What made it seem so great at the time?

Lena:

Well, according to the newsletter, it came through college friends. They were starting a venture capital firm, and this was their big their big pitch. And it wasn't just any company. It was positioned as a direct competitor to Netscape. Now you have to remember the context back then.

Lena:

Netscape was, I mean, huge.

Reed:

Oh, absolutely. Netscape basically was the Internet for a lot of people. Yeah. So, yeah, a competitor. That sounds like massive disruption potential and huge returns presumably.

Lena:

Exactly. That was the allure. And apparently, the excitement was just infectious. The projections they showed were incredible, staggering potential returns were talked about. The feeling was this is it.

Lena:

This is the shortcut. A real FOMO fear of missing out kind of thing was probably going on.

Reed:

You can see how that happens, but it's a good reminder, isn't it? Even when something sounds amazing, you need that critical eye, which brings us to the next part where maybe some alarm bells should have rung.

Lena:

Right. Brent's very open about this. He didn't actually have the money to invest, which is, you know, a pretty big hurdle. But he was so sold on this golden ticket idea that he made, well, what he calls a pretty bold, maybe impulsive decision.

Reed:

Impulsive seems fair. He took out a cash advance on his credit card, something like $5,000 or $6,000 just to get in. It really speaks to that maybe youthful confidence, that feeling you can somehow gain the system, find the loophole.

Lena:

Totally. He lays it out. He was already planning, you know, paying off student loans, upgrading his car, making more investments, all riding on this one bet.

Reed:

And for a little while, maybe it seemed okay. The newsletter mentions there were some positive updates early on from the company.

Lena:

Yeah. Initially, there were reports suggesting things were moving forward. So he and his friends who were also in on it, they were feeling pretty good, sharing the news, building anticipation.

Reed:

But like often happens in these scenarios, the communication started to, change.

Lena:

Exactly. Updates got less frequent. Then when people ask questions, the answers became vague, less concrete. That initial buzz started to fade into like uncertainty.

Reed:

Which unfortunately often signals trouble ahead. And then the newsletter describes the inevitable, the company collapsed. The investment was gone.

Lena:

Completely gone. Worthless. A total loss. And it wasn't just him. His friends who'd invested were in the same boat.

Lena:

That lottery ticket turned out to be a pretty costly lesson.

Reed:

And this is where the story really shifts, think. From just telling what happened to analyzing why. Brent points to three key questions he just didn't ask beforehand. This is where the real value is, I feel. Three simple questions with big implications.

Reed:

Let's start with the first one he mentions, the management team.

Lena:

Right. He trusted his friends, the one starting the VC firm, but he admits he knew basically nothing about the actual people running the company they invested in. He didn't check their experience, their leadership skills, their track record. It really highlights how crucial leadership assessment is, doesn't it? You need to know who's steering the ship.

Reed:

Absolutely. It's not just about the idea. It's about execution. And that comes down to the team, their experience, blind faith, even in friends. It's not really a strategy.

Reed:

Whether you're investing or building a team yourself, you need to know who you're working with, what they bring to the table, not just trust the concept blindly.

Lena:

Then the second question he missed was about the product itself. Okay. It's an Escape competitor. But how? What made it better, different?

Lena:

He realized later he never actually understood its competitive edge. Why would anyone switch from the dominant player?

Reed:

Precisely. What was the unique selling point? Where was the value proposition? It speaks right to performance, you know, and doing your homework, your due diligence. You can't just buy into the hype.

Reed:

You need to understand the fundamentals. What makes this thing actually work, actually compete? That's vital for high performance in any area.

Lena:

And the third blind spot, the market. Just because you want to be the next big thing doesn't mean there's actually room or demand for you.

Reed:

He admits he had no real grasp of the market conditions, the actual need. The decision was fueled by excitement, the dream of a quick win, not by, like, solid market research or strategic thinking.

Lena:

It's quite a reflection really how the excitement and the desire for that shortcut completely overshadowed the basic necessary investigation, which leads right into the next big theme he explores.

Reed:

Yes. The whole idea of shortcuts. This is where it becomes less about just this one investment and more about well life in general, leadership, goals, personal growth. He makes the point pretty strongly. Shortcuts rarely if ever lead to lasting success.

Reed:

Sure. There are outliers, lottery winners, maybe that one startup that blows up overnight, but they are absolutely the exception.

Lena:

Yeah. He gives some great grounded examples like real investment growth usually comes from compounding over years, consistent effort, sustainable weight loss, same thing ongoing changes, not a quick fix. Even those businesses that look like overnight successes often there are years of grind, struggle and persistence behind the scenes that you just don't see.

Reed:

And there's a subtle but I think important critique in there about our culture. We tend to celebrate the quick win, the instant result. This newsletter offers a really valuable counterpoint, real achievement, the stuff that sticks usually takes time, effort, and pushing through setbacks.

Lena:

Absolutely. The core idea is that the people who really succeed long term in whatever field are the ones willing to play the long game. To put in the work, navigate the tough stuff, and just keep going. No real magic bullets.

Reed:

Which brings us back to that intriguing phrase he uses, my worst best investment. Obviously financially it was terrible in the short run. Lost money, bruised ego probably.

Lena:

But, and this is his key point, the lesson learned from that failure patience, about persistence, about actually doing the work and asking the right questions, that lesson was incredibly valuable. It fundamentally changed how he approached things later on. So in the long run, maybe it was one of his best investments, just not in a financial sense.

Reed:

Exactly. It really underscores that idea that failure isn't always just failure. Sometimes it's the most powerful teacher. The financial hit was real, but the wisdom gained. That likely paid off many times over down the road, And that connects directly back to performance and well-being too.

Reed:

You hit setbacks, you learn, you adapt. That resilience, that consistent effort even after a fall, that's what builds lasting strength.

Lena:

And he wraps up the newsletter with that clear message. Whether it's investing, building something, or changing something in your own life, resist the shortcut temptation. Play the long game. Stick with it. Keep going.

Lena:

That's where the real returns are found.

Reed:

So I guess the big takeaway is that the process, the journey, the learning from the challenges, that's often more valuable than finding some imaginary quick fix. That resilience, that perspective, it's fundamental for leadership, for performance, for just navigating life well.

Lena:

So here's something maybe for you, the listener, to think about. Can you recall a time in your own experience when something felt like a failure, a real setback, but looking back, it taught you a crucial lesson? Maybe something about leadership, how you perform, or even just about your own personal journey. What did that tough experience ultimately give you?

Reed:

Yeah. That's a powerful exercise. Reframing those bumps in the road and seeing the value they might hold.

Lena:

Well, this has been a really fascinating look into this particular Rivr Notes. Thanks for sharing your thoughts on it.

Reed:

My pleasure. Really interesting stuff.

Lena:

Goodbye. Until next time.

Andy:

That's it for this week's episode of Rivr Conversations. Speaking on behalf of Brent and myself, big thanks to our expert Rivr Guides for another thoughtful discussion. We always appreciate the unique perspectives they bring to these conversations. To close out each Rivr Conversation, I'd like to describe the photo featured in the Rivr Notes newsletter. It's not just a stock image, it comes from a real adventure.

Andy:

After all, the best ideas often come from staying curious, embracing new perspectives and engaging with the world around us. This week's photo captures a golden moment deep in the heart of autumn. You're standing in the middle of an aspen grove, where the trees stretch high and lean gently toward the sunlight. Their leaves, brilliant shades of gold and amber, glow against a clear blue sky, catching the light just right. Sunbeams filter through the canopy, casting a warm shimmer across the forest floor, which is carpeted with fading greens and the first touches of fall decay.

Andy:

There's a sense of movement here, even in the stillness. Maybe it's the way the trees tilt, like they're in mid whisper, or the way the underbrush sways slightly, suggesting a breeze just passed through. You can almost hear the rustle of the leaves and the faint sound of a stream trickling somewhere nearby hidden, but present. It's a place that feels both wild and welcoming a moment that reminds you to look up, to breathe in, and to let the quiet clarity of the season settle into your bones. If you'd like to read the full Rivr Notes article, including all the amazing photographs, you can find it at OnRivr.com.

Andy:

That's Rivr without an E. And be sure to subscribe wherever you listen to your podcasts so you never miss a conversation. Before we go, a quick reminder: The opinions and viewpoints expressed in this podcast are solely those of the presenters and our AI companions, sharing personal reflections and perspectives. We're not legal experts, medical professionals or therapists. This content is for informational and entertainment purposes only, so please consult the appropriate professionals when you need advice or support.

Andy:

Thanks again for listening. Rivr Conversations is an OnRivr, LLC production.