Diversification: The Thin Line Between Investing and Gambling
Join me live today for SuperCrowdHour and learn why diversification is the key difference between gambling and investing
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Watch Live at 9:00 AM Pacific
At 9:00 AM Pacific / 12:00 PM Eastern today, we’re going live with SuperCrowdHour—and you can watch for free, right here, in the video player at the top of this post.
Finding the Line
If you’ve ever wondered whether investing sometimes feels a little like gambling, you’re not alone. The truth is simple and powerful: diversification is what separates investors from gamblers. That’s the theme of today’s SuperCrowdHour, and if you hit play on the video above, you’ll get a brisk, highly practical walk-through of how to build a diversified impact portfolio—without sacrificing your mission.
This session is built on the chapter from my book, How to Make Money with Impact Crowdfunding, where I argue plainly: “Don’t gamble with your investment money. Diversify.” We translate that principle into an actionable framework you can use right away. Below is a quick guide to what you’ll learn, why it matters, and how to get even more from the experience—including asking questions live during the stream and joining me for a VIP small-group session immediately after the webinar.
Why Diversification (Really) Matters
We open with a thought experiment from the book: imagine you have $10,000 to invest in impact crowdfunding over the next few years. You could put it all into a single deal—or you could spread it across many. Concentration feels simpler, but it’s closer to a lottery ticket than a portfolio. A single winner can make you look brilliant; a single failure can erase years of careful saving.
Diversification, done deliberately, changes the math. It reduces the chance that one bad outcome derails your plan and increases the likelihood that the overall portfolio behaves the way you intended. During the session, I use simple visuals to show how moving from “one big bet” to “many small positions” shifts your risk from existential to manageable.
Key takeaway: Diversification turns luck into strategy.
The Three Dimensions of Diversification
Most advice stops at “own more than one thing.” We go further, laying out three distinct dimensions you can use to craft a stronger, more resilient impact portfolio.
1) Public vs. Private
Public markets (stocks, bonds, ETFs) and private, direct deals (like Reg CF offerings) aren’t perfectly correlated. While both respond to economic forces, they often do so differently and on different timelines. Adding a measured slice of direct deals to a public-heavy portfolio can smooth the ride and open doors to real-world impact you can see and touch. We’ll show how to think about that mix—and what “measured” can look like.
2) Across Industries
You can own dozens of positions and still be undiversified if they all swim in the same pond. Climate-aligned investors, for instance, often find themselves concentrated in EVs and solar—two areas that sometimes move in tandem. We explore sector cousins you might be overlooking (efficiency, grid services, storage, materials, circularity, ag-tech, and more) so you can widen your lens without watering down your mission.
3) Real Estate vs. Securities
Over long periods, real estate and equities tend to rise with the economy—but in the short and medium term, they can dance to different tunes. If you already own a home, you likely have some real estate exposure. If you don’t, we discuss ways to add it thoughtfully, including mission-driven projects in the crowdfunding market. We also unpack a critical nuance: a single crowdfunded real-estate deal is one property, not a portfolio—so the diversification principle still applies.
Position Sizing: Don’t Let One Elephant Sit on Your Seesaw
Many investors “overweight their favorites,” allocating 3–5x more to the deals they love. It feels rational—I’ve done more diligence; I’m more confident!—but the math often backfires. If two large favorites stumble while a set of smaller bets perform fine, your overall results can still disappoint.
We’ll walk through a clear, easy-to-apply rule of thumb:
Keep each single position small relative to your net worth.
If you do scale up a position, scale up your due diligence time accordingly.
Consider aiming for balanced position sizes across most of your deals rather than a few heavyweights.
Think of it as weight distribution in a vehicle: better balance, better handling.
Diversifying Who You Back: Founders and Inclusion
Impact isn’t just what you invest in; it’s who you invest in. Many investors intentionally back women and underrepresented founders. We talk about integrating this goal while maintaining diversification across industries and asset types. And for those of us who might unconsciously back people who “look like us” or “went to the right schools,” we discuss practical ways to widen the aperture, find remarkable founders you might be missing, and align your capital with your values—without concentrating your risk.
Practical Moves You Can Make This Month
The webinar isn’t theory-heavy; it’s action-oriented. Here’s a preview of the simple plan we’ll build together:
Portfolio Check-Up: List your current positions, sector by sector, and mark what’s public vs. private, securities vs. real estate.
Spot the Clumps: Identify where two or three sectors (or a few overweight deals) dominate your exposure.
Right-Size New Entries: For your next 5–10 investments, pre-define a position size you won’t exceed.
Widen Your Mission Lens: If you’re climate-focused, consider adding efficiency, grid tech, or circularity. If you’re community-focused, look at local services, workforce solutions, and attainable housing.
Document Your Rules: Write down a short “investment constitution”—your position-size guardrails, your diversification targets, and your diligence checklist. Future-you will thank present-you.
Join Live, Ask Questions, Get Answers
Watching passively is fine; participating is better. During the livestream we’ll share quick instructions for submitting your questions live so I can answer them on air. Bring your toughest dilemmas:
How many positions is “enough” to call my portfolio diversified?
Should I ever double down on a winner—or cut a laggard?
How do I mix public ETFs with direct Reg CF deals?
What’s a sensible entry size for my first real estate project?
If you’re reading this before the event starts, click the player above and set a reminder. If you’re arriving afterward, the replay is right there—hit play and jump to the sections that matter most.
Stay for the VIP Session (Limited Capacity)
Right after the webinar, I’ll host a VIP Zoom session for a smaller group. This is where we can lean into the nuance that’s hard to handle in a live chat: walking through a sample allocation plan, discussing a specific deal structure, or weighing trade-offs in real time. Register here: 4sc.fun/vipsep.
Why This Matters—And Why Now
Volatile markets can tempt us into big, concentrated swings. Mission-driven opportunities can tempt us into narrow sectors we love. But durable impact requires durable portfolios. Diversification is how we stay in the game long enough to make the difference we set out to make.
You don’t have to abandon conviction; you just need to spread it wisely—across asset types, across industries, and across positions. You can back diverse founders intentionally while keeping your balance. You can pursue climate solutions or community prosperity without betting the farm on a single theme.
That’s the heart of this session: be intentional, be balanced, be persistent. Do those things, and your odds of both impact and return rise—together.
Watch, Share, and Bring a Friend
Watch the webinar in the embedded player above.
Invite a colleague who cares about impact, risk, and results.
Come with questions—we’ll show you how to get them answered live.
VIP registration—register for the VIP session here: 4sc.fun/vipsep.
Thanks for being part of this community of doers and builders. Let’s invest like champions of social good—on purpose, with balance, and with the long game in mind.
VIP Session – Only 10 Spots
Immediately after the public webinar, I’ll host a small-group VIP session. This is your chance to bring your project-specific questions and get direct feedback. Space is limited to just 10 participants so everyone can be heard.
👉 Register here.
Impact Members of The SuperCrowd have received a code to register free of charge.
Don’t Miss It
We go live at 9:00 AM Pacific. Watch for free right here in the video player at the top of this post. And if you want personalized answers, be sure to register now for the private VIP session.
Space is limited. Don’t wait.
Support Our Sponsors
Our generous sponsors make our work possible, serving impact investors, social entrepreneurs, community builders and diverse founders. Today’s advertisers include FundingHope, Digital Niche Agency, Ranco Affordable Living and InnerSpace. Learn more about advertising with us here.
Max-Impact Members
The following Max-Impact Members provide valuable financial support:
Carol Fineagan, Independent Consultant | Hiten Sonpal, RISE Robotics | Lory Moore, Lory Moore Law | Marcia Brinton, High Desert Gear | Mark Grimes, Networked Enterprise Development | Matthew Mead, Hempitecture | Michael Pratt, Qnetic | Dr. Nicole Paulk, Siren Biotechnology | Paul Lovejoy, Stakeholder Enterprise | Pearl Wright, Global Changemaker | Ralf Mandt, Next Pitch | Scott Thorpe, Philanthropist | Sharon Samjitsingh, Health Care Originals | Add Your Name Here
Upcoming SuperCrowd Event Calendar
If a location is not noted, the events below are virtual.
SuperCrowdHour, September 17, 2025, at 12:00 PM Eastern. Devin Thorpe, CEO and Founder of The Super Crowd, Inc., will lead a session on "What's the Difference Between Gambling and Investing? Diversification." When it comes to money, too many people confuse speculation with true investing. In this session, Devin will explore what separates gambling from responsible investment practices—and why diversification is one of the most important tools for reducing risk and improving outcomes. Drawing on real-world examples and practical strategies, he’ll help you understand how to evaluate opportunities, spread risk wisely, and think long-term about your portfolio. Whether you’re new to investing, considering your first community round, or looking to refine your approach as a seasoned investor, this SuperCrowdHour will give you actionable insights to strengthen your decision-making. Don’t miss this chance to sharpen your perspective and invest with greater confidence.
Superpowers for Good Live Pitch, September 29, 2025. Hosted by Devin Thorpe on e360tv, this special event gives purpose-driven founders the chance to pitch their active Regulation Crowdfunding campaigns to a nationwide audience of investors and supporters. Selected founders will gain exposure to investors, national visibility across social and streaming platforms, and exclusive prizes from judges and sponsors—all at no cost to apply or pitch.
Impact Cherub Club Meeting hosted by The Super Crowd, Inc., a public benefit corporation, on October 28, 2025, at 1:30 PM Eastern. Each month, the Club meets to review new offerings for investment consideration and to conduct due diligence on previously screened deals. To join the Impact Cherub Club, become an Impact Member of the SuperCrowd.
Community Event Calendar
Successful Funding with Karl Dakin, Tuesdays at 10:00 AM ET - Click on Events.
Neighborhood Economics: Chicago takes place September 29–October 1, 2025, at Venue SIX10, bringing together changemakers, innovators, and community leaders reimagining wealth, ownership, and entrepreneurship to drive real community transformation. For the next two days only, save $200 on registration with promo code CHICAGOFLASH—flash sale ends Thursday at midnight! Register here.
Earthstock Festival & Summit (Oct 2–5, 2025, Santa Monica & Venice, CA) unites music, arts, ecology, health, and green innovation for four days of learning, networking, and celebration. Register now at EarthstockFestival.com.
Regulated Investment Crowdfunding Summit 2025, Crowdfunding Professional Association, Washington DC, October 21-22, 2025.
Impact Accelerator Summit is a live, in-person event taking place in Austin, Texas, from October 23–25, 2025. This exclusive gathering brings together 100 heart-centered, conscious entrepreneurs generating $1M+ in revenue with 20–30 family offices and venture funds actively seeking to invest in world-changing businesses. Referred by Michael Dash, participants can expect an inspiring, high-impact experience focused on capital connection, growth, and global impact.
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