About
I came into venture capital through the operator’s door.
Before investing, I spent…
Articles by Richard
-
Five lessons from $17M raised to transform an archaic industry
Five lessons from $17M raised to transform an archaic industry
Three years ago, Ian Padrick walked into a room full of people running businesses that hadn’t changed in fifty years…
5 Comments -
SpaceX S-1: The 5 Strategic Layers Worth More Attention Than the Valuation
SpaceX S-1: The 5 Strategic Layers Worth More Attention Than the Valuation
In 2019, I wrote the first Cape Fear Ventures check into SpaceX. The company was worth around $30 billion.
20 Comments -
The Missing Traffic Control Layer for Orbit Is Here: Scout Space Closes $18M Series A
The Missing Traffic Control Layer for Orbit Is Here: Scout Space Closes $18M Series A
One of our portfolio companies, Scout Space, just closed an $18M Series A. We invested in late 2024 with the founding…
9 Comments -
How A Podcast on A Long Drive Home Led Me To Build a CEO Retreat in My 50s.
How A Podcast on A Long Drive Home Led Me To Build a CEO Retreat in My 50s.
Back in 2024, I was driving home from Wilmington to Virginia, flipping through podcasts, bored stiff. I landed on Mel…
5 Comments -
Rethinking Connectivity: 3 Hard Lessons from Hurricane Helene
Rethinking Connectivity: 3 Hard Lessons from Hurricane Helene
I’m from western North Carolina and have deep connections to Appalachian State University, the town of Boone, and…
9 Comments -
AI on the Menu: 5 Ways Tech Will Transform the Food and Beverage Industry
AI on the Menu: 5 Ways Tech Will Transform the Food and Beverage Industry
The food and beverage industry isn’t the first to come to mind when discussing the impacts of AI and emerging…
18 Comments -
The Business Case for Space: 3 Reasons Why Cape Fear Ventures Targets Emerging Aerospace Opportunities
The Business Case for Space: 3 Reasons Why Cape Fear Ventures Targets Emerging Aerospace Opportunities
I started investing in SpaceX in 2019 because I realized the potential business impacts of advanced aerospace…
28 Comments -
4 Foundational Elements for Investing Amidst High Interest Rates and Rapid Innovation
4 Foundational Elements for Investing Amidst High Interest Rates and Rapid Innovation
One of the perplexing aspects of VC today is that founders and investors are faced with rapid innovation within a…
2 Comments -
3 Key Insights on AI, VC, and the Future of Innovation
3 Key Insights on AI, VC, and the Future of Innovation
AI-related startups raised almost $50 billion in 2023, about one-third of the capital invested across all U.S.
16 Comments -
Navigating the Partnership Jungle: 3 Crucial Tips for Founders Seeking the Right VC and PE Investors
Navigating the Partnership Jungle: 3 Crucial Tips for Founders Seeking the Right VC and PE Investors
Entrepreneurs and startups face a daunting challenge when it comes to raising capital and scaling their businesses:…
5 Comments
Activity
23K followers
-
Richard Stroupe shared thisMany founders treat coaching as a soft add-on. Andrew Sridhar thinks that's backwards. His argument: your performance is directly tied to your ability to stay positive, optimistic, and resilient. Those are direct outputs of what's happening inside your head. And if you don't address what's in there, no amount of strategy fixes it. Confronting questions surface what's running the show, leading to what Andrew calls elite performance from the inside out. ____ Listen to Andrew Sridhar's full episode on the Amplified CEO — why your inner state sets the ceiling on your results, what "the burden of command" feels like for founders, and what separates founders who execute from the ones who stay stuck in analysis. Full episode linked in the comments
-
Richard Stroupe shared thisAt a founder hot seat this week, five companies each got 30 minutes of brutally honest peer review. It was worth 1000x any pitch competition I've sat through. Five takeaways: → Honest peers beat an applauding audience A pitch competition rewards performance, so founders sand off the hard parts. A hot seat is a room full of people trying to find the cracks before the market does. Only one makes your company stronger. → Get your house in order before you raise A team aligned on the same plan. Customer acquisition you can explain with numbers. Traction, and a growth plan a stranger can follow. Above all, true product-market fit, not solution-market fit. Solution-market fit = customers agree your product works. Product-market fit = they buy it, at a price that sustains the business, and buy again. → Spend more time in customer interviews than feels productive You're listening for two things: 1) What they'd pay to make the problem go away 2) What switching would cost them in time, retraining, and risk Your value has to clear both. → Put a date on the calendar, and a market checkpoint to hit by then If the market is pointing somewhere else, pivot, or go get more customer feedback until the picture is clear. A plan without a deadline is how good teams lose years. → Watch your own bias Conviction built your company, but it can also deafen you. Catch yourself hearing every "yes" at full volume and filing every "no" as the exceptions. The feedback that contradicts you most is usually the piece worth studying. ____ P.S If you're a founder doing ~$250K–$3M ARR and you can feel the company leaning on you too hard, The Elevate CEO Retreat is where we fix that. You'll leave with a 90-day execution roadmap, clarity on your top constraints, and systems that make the business run without the founder as the operating system. Next cohort October 26-29 Details here: capefear.vc/elevate
-
Richard Stroupe shared thisOn Monday night, five founders sat in the back room of Wrightsville Beach Brewery and let a room full of peers take their businesses apart. Jim Roberts and I ran a private / invite only "Tech Startup Tune-Up" working session as part of the Network for Entrepreneurs in Wilmington. 30 minutes per company on the hot seat: The real state of the business, what's getting in the way of growth, and why they believe they'll win. Then open questions from advisors and the other founders in the room. I sat through this same format at Harvard Business School while scaling my own company, and the hot seat is day one of my Elevate CEO retreat for a reason. Rooms like this catch expensive mistakes before you make them. Respect to those who took the seat: Tully Ryan [IQExit] Robert S. Cooley, Jr. [NUREAM] AJ Trelease, [CareHome Technologies Inc] Morris Nguyen, [Predicate AI] Shishir Desai with Carson B. Jackson [Ouro Labs] It takes real grit to open the books in front of your peers and to say out loud what’s working, what’s broken, and what you’re afraid might be true. Most founders only do that in private: with a co-founder, a spouse, or a late-night notebook. The hot seat forces a different muscle. You walk into a room where nobody is paid to applaud you, and you let people who’ve built companies stress-test your assumptions in real time. That discomfort is the point. The fastest way to waste a year is to protect your ego from useful feedback. So yes: it takes grit. But it’s the productive kind. The kind that turns one hard conversation into a cleaner plan, a tighter story, and a company that gets stronger before the market forces the lesson. Every one of them left with a sharper picture than they walked in with. So did I. ____ Thank you Jim for hosting through NEW and inviting me to facilitate, Paul Salisbury Tom Collopy and Tom Snyder for advising alongside me. That's how an ecosystem should work. I took a few pages of notes on what separates founders who are ready to raise from founders who aren't. Sharing the five biggest lessons tomorrow.
-
Richard Stroupe shared thisThree signals told me to sell my first company. Only one of them was in the P&L. When founders ask me how I “knew it was time to sell” they expect a market answer. That matters. But by the time I first pulled the trigger in 2009, three separate dashboards were flashing at once, and only one was financial. Here are the three signal categories for the founder thinking about exiting. First, your body and state of mind. I was engineering by day and running the business at night, pulling 80-hour weeks. I had health problems because I wasn't taking care of myself. I had family strain because I was never home. When the physical cost of staying running at that pace stacks up, you’re looking at a bill coming due. Second is your team. Who's stretched past their ceiling. Whether the next stage of growth needs capabilities the current roster doesn't have. Whether the people who built the business are the right people to scale it. A team that's hit its ceiling is one of the clearest reads that the company needs something different. Third is your market. From 2003 to 2008, intelligence-community tech spending ran hot off the post-9/11 build-up. By 2009 we could see the plateau coming. Especially with the new direction established by the new administration. The crossroads was clear: differentiate into new markets and double down, or sell into strength while valuations held. We sold. Founders today face the same crossroads with a different driver, with AI rewriting unit economics across whole categories. It's a legitimate question whether some business models will be less profitable five years from now. That's Signal 3 - but it’s worth asking whether Signal 1 and Signal 2 are already stacking underneath it. The market signal is one part, the other two will tell you whether you'll have the energy and the team to capitalize on it. __ I covered all three of these signals, and what to do once they're stacking. in my conversation with Steve McGarry on The Exit podcast. We got into diligence prep, buyer selection, and how to read the market without waiting too long. Full episode: https://lnkd.in/eKvHv_2Z
-
Richard Stroupe shared thisThe pain you feel at the edge is proof you're in the right place. Whether it's one more rep the gym, getting up at 5am training for a physical challenge, or making the business decisions you’ve been circling on … The skill is finding where discomfort starts and operating just past it. ____ Andrew Sridhar spent his career learning what real discomfort looks like - from Hell Week to combat ops to executive coaching. In this episode of The Amplified CEO he breaks down how to build elite performance from the inside out, what separates operators who grow from ones who plateau. Catch it here: https://lnkd.in/edBQWCdB
-
Richard Stroupe shared thisIf you want to know what's limiting your business, disappear for 30 days. It's the clearest signal of how much your business runs on you personally versus systems. Typical symptoms for founders stuck between $250,000 and $3,000,000 ARR: → Your sales pipeline freezes up Deals at the proposal stage sit unanswered because you're the one who "really knows the client." New conversations don't open because prospects want to "talk to the founder." → Key decisions queue up and rot Vendors stuck waiting on approvals. A client issue that needed one sentence from someone with authority. The business slows to a crawl while everyone waits for the clearing house to return. → Client relationships wobble The clients who signed because of a personal relationship start asking where you are. If the client would call you on a Sunday but wouldn't know who else to call on a Monday, the relationship needs, at least partially, transferred. → Your team stops making calls Good people hedge. They cc: everyone. They write longer emails. They wait. A direct result of the culture the founder built by being the answer to every question for years. Why is it so hard to fix from the inside? The founder-as-doer process is ‘working’. Clients are happy enough. Decisions get made. Revenue is growing. The dependency doesn't feel like a problem because you're still there to paper over it. The day you go dark is the first day the real architecture is visible. Now, you're not going to disappear for 30 days. But you will take a week off at some point. Pay attention to what slips. What piles up. What your team held until you got back instead of handling while you were gone. See what breaks. Then fix that before you fix anything else. _______ At Elevate CEO we run this diagnostic on day one. It’s a 72-hour intensive, next cohort October 26–29, for founders at $250K–$3M ARR, in coastal North Carolina. You’ll leave having installed the systems to fix it, including a Calendar Firewall that protects your time, a Playbook Layer that captures how the work gets done, and an IP Transfer that means what you know doesn't leave when you’re not around. $2,000 investment, details here: https://lnkd.in/e77bGiFZ
-
Richard Stroupe shared thisI took three recently exited founders to lunch before I hired a banker, a lawyer, or anyone else. I walked into my first sale already knowing who had lost the last deal, who the hungry buyers were, and what the floor on price looked like. Full context is in my conversation with Steve McGarry on The Exit podcast. We get into the preparation process, PE vs. strategic deal structure, and diligence blind spots. Full episode here: https://lnkd.in/eKvHv_2Z
-
Richard Stroupe shared thisAt 26, I was a solo 1099 Oracle contractor. By 50, I had built and sold two software companies, made 50+ startup investments, got into commercial real estate projects, and launched my own venture fund. I sat down with James Allen on the Profit Your Knowledge podcast to talk through the real arc between those two points. One thing I said that founders should sit with. 90% of the time, when you’re stuck between $500K and $3M ARR and can't figure out why you can't get to $5-10M ... you're the problem. You're the chokepoint. Your won't delegate. Your haven't built the structure that can hold more than they personally can carry. And until you get out of your own way, you'll stay where you are. That’s what I see over and over, and it's what we spent a lot of this conversation unpacking. We also covered: → The 4Ts I use to evaluate every startup: Team, Technology, Traction, TAM, and why Team is the most important in my experience. → How one of my earliest investments pivoted hard, and what the team had that made it stick → Why closing the biggest deal of my life was the start of a deep depression If you're in the thick of it right now, building the team, figuring out the model, wondering when it starts to feel less reactive, this conversation is built for that moment. Full episode linked here: https://lnkd.in/ehuSYdAU
-
Richard Stroupe shared thisMerging my identity with my startup was the most expensive mistake I made. Founder-builders do it constantly because of this faulty belief: "Nobody else can do what I do". I ran my first company as a software engineer by day and a CEO by night. The product was my craft, and every decision ran through me because I thought the standard would slip if it didn't. You make a decision faster than delegating it would take. Then another. Then it's your name on the door, your face on every client call, your judgment on every deliverable, and the company has learned to wait for you rather than run without you. And the longer you continue like that, the more certain you become that nobody else can do what you do. But it's not true. You can document processes, hire well, grant autonomy, and train up great people. Fusing yourself with the company becomes an enormous dependency drag. That's why you need to treat it as a separate entity. Trust your team. Equip them with your documented judgment. Protect your family time. Keep a life outside the office walls. Do what you need to do as a parent or a spouse. That psychological separation is key for your health. But there’s a commercial reality underneath it too. The tighter the merger between founder and company, the harder the exit, and the more the buyer knows it. Buyers don't just price what the company is worth. They price what it's worth without you. Those are two different numbers, and the mismatch between them is founder dependency. So, two entities. You on one side, and the company on the other. _____ P.S. If any of this landed, the next step is doing something about it. Elevate CEO is a 72-hour retreat (next cohort October 26–29) built specifically for founders at $250K–$1M ARR, the stage where the identity merger is tightest and the cost of staying in it is highest. Ready to put real systems under your company? Details and application here: capefear.vc/elevate.
Richard Stroupe commented on a post
17h
The presentation you gave on this at Elevate CEO was excellent!
-
Richard Stroupe liked thisRichard Stroupe liked thisOnly Sweden would think of this. 🇸🇪 Instead of paying people to collect cigarette butts, A startup built a machine that rewards wild crows with peanuts every time they drop one in. No long training sessions. The crows figured it out by watching each other. I love this because it shows a different way of thinking about AI. The goal isn't always to replace humans. Sometimes it's to build systems where technology and nature work together. The smartest solution isn't always the most complicated one. Would you trust crows to help clean your city? Want to get good at AI? Book your free 15min discovery call here: https://lnkd.in/e3szQMAD
-
Richard Stroupe reacted on thisWe don't get much R-E-S-P-E-C-T in our own state of #NorthCarolina But some positive ECONOMIC things are happening in #WilmingtonNC #JOBS #HiringRichard Stroupe reacted on thisLinkedIn's new list of cities with major job growth shows one industry dominating the hiring—and it's not tech. https://trib.al/J1osk6pLinkedIn's 25 Fastest-Rising U.S. Cities for Jobs Have 1 Thing in CommonLinkedIn's 25 Fastest-Rising U.S. Cities for Jobs Have 1 Thing in Common
-
Richard Stroupe liked thisRichard Stroupe liked thisCreating better connections with your team... One of the best outcomes managers realize with Forté is a conversation that doesn't end with someone saying, "I've accepted another offer." Just as important is the conversation where a team member says: "I didn't realize you noticed that." That moment when a real connection occurs and someone feels genuinely seen by their manager, and they realize the person leading them has actually been paying attention to how they are doing and not just what they are producing. Most managers care deeply about the well-being of their team members and want to create that moment. Very few have the information they need to create it consistently. Forté supports those very moments. Life goes on; Forté is not once-then-done. What if every person on your team had that moment with you in the next 30, 60, or 90 days?
-
Richard Stroupe liked thisRichard Stroupe liked thisYou might already be paying a manager's salary to someone who is not doing manager work. Before you post the job for a new hire, check your current payroll first. This gap is more common than owners think. Someone earns more than the rest of the floor because they have been there the longest or because they stepped up once during a crisis and the raise never got revisited. Years pass. The pay stays elevated. The responsibility never caught up to it. That gap has to close before a new manager walks in. If it does not, the new hire arrives to find someone already being paid like a manager who was never asked to act like one. That person will not accept a stranger giving them direction. The new manager either fights for authority on day one or avoids the fight and lets that person keep running things unofficially. Here is how you actually audit it. List every employee earning above line staff wages. Write down what they are responsible for today, specifically, not what their title implies. Compare the two. Where the duties are real, keep them in leadership and adjust their role to sit underneath the new manager with defined responsibilities that match what they are already paid. Where the duties are not there, you have two options. Expand what they own until the pay is justified. Or reset the pay to match what they are actually doing. Decide before the new manager starts, not after. Some of these employees will become strong shift leads under the new structure. Some will not meet the bar once the standard is written down. Know which is which before you hire, so the new manager inherits a clean org chart instead of a political one.
-
Richard Stroupe liked thisRichard Stroupe liked thisThere's an invisible line through every market. On one side are the customers you can win. On the other, the ones you can't. An MIT professor spent 14 pages showing how to find that line in a little-read 2016 paper "Iterating to Insight" Here's the MIT insight method made simple: 1) Every business school teaches strategy frameworks. Very few teach how to think with them. 10 years ago, Duncan Simester at MIT Sloan wrote down the missing part. 2) You find the line the way Einstein found relativity. He couldn't experiment on the universe, so he ran the experiments in his head: Propose a scenario, test it against what's known, adjust, repeat. Markets yield to the same method. 3) Start absurdly small: one customer with one need, not a segment. Eg: Bill, 23, lives on Cape Cod, and cares about nothing except phone coverage. Ask a fixed question: can Verizon win him? Yes. 4) Now change exactly one variable. Move Bill to Long Island, where a rival's coverage is better. Can Verizon win him now? No. The answer flipped, which means you just stepped across the invisible line. Now you know where a piece of it runs. 5) Repeat, flipping one variable at a time: the need, the competitor, the partner. One at a time is the law, because if you change two things you can't tell which one moved the answer. The paper's image for this is toddlers with playdough: keep the colors separate and patterns appear. Mix them and all you get is brown. 6) The flips produce insights, and insight has a strict definition: surprising, yet compelling. 7) The engine under the whole method is a single question, aimed at every belief you hold: when is it not true? Most people ask whether something is true. Strategists ask when it stops being true. ________ Since I first read this paper I've gone back to it many times because it's such a usable read. Ask "When is it not true?" at every turn. It's the sharpest question in strategy. And the cheapest. It costs nothing and it finds the line faster than any framework.
-
Richard Stroupe liked thisRichard Stroupe liked thisFormula 1 Racing and M&A has more in common than you may think… Because, as you may know, “Slow is smooth, and smooth is fast.” And that's exactly the mentality that founders should be taking when preparing for an exit. A lot of business owners get overwhelmed by the idea of exit prep. So they push it to next week. And then the next. And it just keeps getting pushed. That’s why I like the F1 mantra. How are you going to win a 60-lap race if you can’t change the tires in under 3 seconds? Said more simply, do the little things well, and the big things will follow. I can't tell you the number of early call clients that can’t immediately produce fully executed agreements for their top 10 clients. One document isn’t countersigned, one is a paper copy but missing pages, etc. etc. No judgment zone here, I've been in the same spot myself. We're busy, and we will “get to it tomorrow.” But, if you can’t do the basics well, how can you expect your team to accomplish the big visions you’ve created? And more importantly, how are you going to finish the M&A race, if you can’t even get off the starting line.
-
Richard Stroupe liked thisRichard Stroupe liked thisWhat made my company software company so valuable was the level of access we enjoyed. For our size ( ~ 250 people at peak) we held prime contracts with some of the hardest agencies in the country to get into. It started with putting myself out there. Nobody had heard of me, so I wrote for trade magazines and spoke at conferences until I was known as an expert. That's the only reason one agency found me at all. Then, when they cracked the door open with one small project, I over-delivered like my life depended on it. I rewrote the whole thing night and day and handed it back better than they expected. And then the timing hit. 9/11 happened, they needed people who'd already proven themselves, and I was the name that came up. That part I didn't control. But I'd put myself exactly where that kind of luck could find me. What you can do is make yourself visible, over-deliver like crazy the first chance you get, and be the obvious person to pull through the door when the moment arrives. _____ This came from my chat with Raman Sehgal on the NexChapter podcast. We got into building the company from a kitchen table on 20-hour days, the moment I had to stop writing code to unlock growth, and the selection process that made us the A-team in our niche. Full episode here: https://lnkd.in/e8_pnkPy)
Experience
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
Education
-
-
-
-
-
-
-
-
-
-
-
-
-
Publications
-
A Qualitative Comparative Analysis of Data Breaches at Companies with Air-Gap Cloud Security and Multi-Cloud Environments
Purdue University
See publicationThe purpose of this qualitative case study was to describe how multi-cloud and cloud-based air gapped system security breaches occurred, how organizations responded, the kinds of data that were breached, and what security measures were implemented after the breach to prevent and repel future attacks.
-
Extending Oracle’s High Availability Framework with 10g Cluster Ready Services (CRS)
Select Journal, Volume 12, No.3, 3rd Quarter
-
Tips on Successfully Installing Oracle Applications 11i on Windows 2000/NT
Select Journal, Volume 10 No. 3 3rd Quarter 2003
Patents
-
System and Method of Emulating a Cloud Computing Environment
Issued US 11,528,254 B2
Other inventors -
Recommendations received
6 people have recommended Richard
Join now to viewOther similar profiles
Explore top content on LinkedIn
Find curated posts and insights for relevant topics all in one place.
View top content