Colleen Thom

There’s a hidden cost in business no one talks about: Decision fatigue. As a founder, you’re not just making big calls, youre making dozens of small ones daily. Which client to prioritize. Which operator to trust. Which opportunity to pass on. Which standard not to bend. Individually, they feel minor, but they define the company. In private aviation, small decisions compound fast. One overlooked detail becomes operational friction, and one rushed approval becomes reputational exposure. Over time, I’ve learned something simple: Protect your mental clarity like you protect capital. Because the quality of your thinking directly determines the quality of your outcomes.

54

14 Comments

If you are a startup raising money, I'm going to save you a TON of time with this post. Stop asking for warm introductions and doing cold outreach when you aren't ready for funding. This is the mismatch that exits in today’s market... Nearly all founder/CEOs think their company is fundable. But almost NONE are. Nearly all investors, especially VCs, have ZERO VISION. Yes, they all want to invest in the best deals and make an obscene amount of money. They also want to avoid like the plague any deal where they will lose money. Startup founders want VCs to be risk taking. They are not. They are risk averse. How do you get investor to invest? 1) Make sure you are the right fit for the target investor. Right stage, right thesis, right check size to lead your round, 'dry powder' capital to invest, actively investing in your sector, and can add value beyond money (introductions, domain expertise, network). 2) Have the proper investor materials (one liner, elevator pitch, exec summary, 12 page investor pitch deck, investor deck appendix for key questions, FAQ). Always leave investors wanting to learn more. Have them leaning-in. Raising capital for a startup is a process not an event. Especially with VCs and large check sizes. There are always less than a handful of exceptions to this rule, and they get a lot of press. You aren't that person and you don't have that company. 3) Know your numbers cold. Be able to crisply explain everything about your business. Slides are a VISUAL AID. Be able to answer 90% of questions on the spot. Get back quickly for the other 10%. Remain teachable and coachable. 4) If there is 'hair on your deal', give it a haircut. Clean it up. This is different at various stages (pre-seed, seed, Series A, Series B, etc.). Outline and mitigate risks. Demonstrate traction. Know your Go-to-Market Strategy, Product-Market Fit, Competitive Positioning, and Team Expertise. Shaving the hair off your deal is different than putting 'lipstick on a pig'. One is a clean-up, and the other is a cover-up. All cover-up eventually get exposed. If you don't clean things up, and you still get funded, you will likely get a different type of haircut...a haircut on your valuation. 5) When asking for warm introductions, consider the source and their connection to the target. Good sources: (A) an founder/entrepreneur that is in the current or recent portfolio of the investor - you have a good relationship with them and they have a good relationship with the investor; (B) a current investor in your company; (C) a principle in a incubator/accelerator program that has a track record of making great recommendations. Bonus Tip: Make sure your investor materials can be understood by a sixth grade child with the attention span of a goldfish. VCs are typically Harvard or Stanford MBA, so this approach isn't because they are dumb. They look at thousands of deals and invest in very few. Make it easy for them. #startup #founders #funding #strategy

125

56 Comments

OPay went from banned bikes to processing $3B every month in just 18 months. The pivot nobody believed would work. February 2020. Lagos banned motorcycle ride-hailing. Overnight, OPay’s entire business model collapsed. • 1,000+ bikes • Thousands of drivers • Millions in VC funding tied to transportation Most people said the same thing: “You’re finished.” But instead of mourning the loss, OPay made a decision that changed African fintech forever. They pivoted. Not because it was easy but because they saw what others ignored. 60+ million Nigerians without bank accounts. Failed transactions taking days to resolve. Agent banking that barely worked. OPay went all-in on payments. From moving people to moving money. From bike drivers to 300,000+ agents. From transport to financial infrastructure. The results were unbelievable: • December 2020: $2B monthly volume • August 2021: $3B monthly • 2024: $12B processed every month That’s $400M every single day. • 5M users in 2021 • 50M+ users by 2024 • Serving nearly 25% of Nigeria’s population But here’s the real lesson: OPay didn’t just pivot, They solved the problem everyone avoided. While banks built for the wealthy, OPay built for everyday Nigerians. While competitors fought for market share, OPay created an entirely new market. The startup many dismissed is now valued at $2.75B. The company people thought would die with the bike ban became one of Africa’s most powerful fintechs. Because sometimes: Your biggest crisis is your biggest catalyst. The end of Plan A is the beginning of something bigger. And when the obvious path closes innovation opens. OPay went from banned to billions. From moving bodies to moving money. So here’s the real question for every founder: What impossible pivot is waiting on the other side of your crisis?

3

People sometimes ask me: “Is WingRep competitive with Gong?” That’s like asking: Is a co-pilot competitive with a cockpit? They’re on the same plane. But they play different roles. A modern cockpit is incredibly powerful. It’s packed with systems, controls, and data. In the hands of a skilled pilot, you can do remarkable things. Gong does an exceptional job capturing reality and making sense of it. It tells you what happened. But flying at scale isn’t about adding more controls. It’s about reducing cognitive load at the exact moment it matters. That’s where a co-pilot comes in. A co-pilot doesn’t replace the cockpit. It helps you: • focus on the right thing • make fewer decisions • adjust in real time • land the plane consistently Most sales tools are optimized for analysis after the fact. Most sales teams are humans operating under pressure. WingRep is built for that moment: • when the deal is live • when attention is scarce • when execution matters more than insight Same plane. Different roles.

17

I spoke with a YC founder whose first pitch got torn apart by Dalton Caldwell, and it changed everything they thought they knew about fundraising. Their original deck hit every YC template point perfectly. Problem, solution. Market size. Traction. Team. Dalton's response: "This doesn't get investors excited." He asked them one question that changed their entire strategy: "If an investor is betting on you having a 0.1% chance of being a unicorn, what does that story look like?" Instead of "we solve X problem for Y customers," it became "we're building the infrastructure that will power Z massive outcome." It's always about painting the vision of what success actually looks like at scale. Lesson for founders: Early-stage investors aren't buying your current traction. They're buying your future potential. They're asking: "Could this become a $10B company?" Your deck should answer: "Why will this be huge?" Everything else is just supporting evidence.

38

9 Comments

Thanks Owen Reynolds for sharing this reflection in public. This is exactly the first line of our pitch. "Venture broke when it turned into PE." Venture is not for safety, it is for risk. That is the return mechanism of the asset class. Many LPs are trading long term returns for short term optics (shiny, established brands). Raising a $50M Fund III I am running into the same reservations. What can be done to take the fear out of the LP's mind? Fear is a horrible guide in venture markets.

8

If you’re a founder raising for AI & B2B SaaS in 2026, these are some early-stage US-based VC funds worth having on your radar. LvlUp Ventures – Los Angeles, CA Pre-seed–Series A. $50K–$250K non-lead checks across B2B SaaS, AI, and consumer. Runs LvlUp Labs, a free accelerator-style program with direct VC access and founder perks. Flybridge – New York, NY / Boston, MA Pre-seed–Series A+. Next Wave writes $50K–$250K; Seed $1M–$3M. Focus on AI infrastructure, developer platforms, and agentic applications. Florida Funders – Tampa, FL One of the most active early-stage funds in Florida across B2B, healthcare, IT, AI, cybersecurity, fintech, edtech, and e-commerce. Hosts the Florida Funders Venture Summit on February 26, 2026. Tech Square Ventures – Atlanta, GA Seed-stage investor writing roughly $500K–$3M checks in B2B, enterprise software, marketplaces, and applied AI. Fuel Venture Capital – Miami, FL Seed to growth across AI, enterprise software, fintech, and consumer tech (US-based fund). Generationship – San Francisco, CA Early-stage fund backing technical women building infrastructure and platform software in the AI shift. Had the pleasure of working with Rachel Chalmers in the past, so this one is for all my wonderful female founders. SuperAngel.Fund – New York, NY Pre-seed–Series A. $25K–$250K checks across B2B software, Future of Work, PropTech, e-commerce SaaS. Link Ventures – Cambridge, MA Pre-seed–Series A. Technical founders building AI-first software. Also operates a venture studio near Harvard and MIT. BVVC – Chicago, IL Inception–Series A. B2B software, hardware, and mission-critical technology, especially relevant for government, industrial, and national security buyers. BITKRAFT Ventures – Denver, CO Seed–Series B. Gaming, interactive media, immersive tech, and AI infrastructure. Not exhaustive and not ranked. Just a slice of funds that founders raising in 2026 may want to study, track, and approach based on fit. 👋 Which funds would you add to this list? Drop others worth knowing in the comments

235

44 Comments