How to avoid 3 red flags that kill your fundraise

Investors are told to ask lots of questions. Here are 22 questions that founders can ask back! This is a great resource, thanks to Christie Jenkins and Techstars Tech Central Sydney Accelerator 🤩

Met a fund manager last week at an event, and after learning about what I do for a living, he asked me what my “end goal” was. Was I building for an eventual exit - to be acquired, or to IPO? It’s quite a common question! I’ve always found this question hard to answer - initially because when Syncio was a startup, the answer I came up with would always be of something tantalisingly big-impact and ambitious and not really about an exit. Something like, “Syncio will become the biggest x in the world”. Whilst I still have ambition on that, I rarely give that answer anymore because it's somewhat disingenuous. Almost like you’re above the financial outcome. A lot of people asking are friends and family, who are generally outside of the ‘startup sphere’, and thus the answer they generally understand is more at a pragmatic-level.  But at the same time, the financial outcome answer falls short. Like of course some sort of exit would be a huge outcome. But this answer feels like the end of the journey, and that makes me feel sad?   So back to the fund manager, I answered with, “I’m just focused on building - I feel that we’re just at the beginning - I’m enjoying building too much to even consider stopping. Work is fulfilling and purposeful, and it’s also sustaining my family and personal life - life is good!” I used to think that this type of answer was a bit of a cop-out because it felt like a deflection. But the question itself corners me into answering a question that’s not hugely important to me, at least not at the present. The fund manager then said that this was a great indicator of success, because most founders that he speaks to are chasing that theoretical exit, or have some predetermined timeline they need to rush to. The problem with that, he said, was that inevitably, he found that these founders burned out, or were left dissatisfied, even if it led to a successful exit. Getting to ‘default-happy’ with what you’re working on and which enhances your life outside of work, is sustainable, and in turn enhances your chances of success, no matter the timeframe. And then it hit me that this was the business that I had designed for myself, and that building it sustainably with each step of the way while increasing exit optionality, was the path for me. Designing the business around my family and health, but in a way that doesn't compromise but rather compliments the business, was a feature I brought to life. Of course, every founder has their own path, obligations, and goals. And that’s cool. Some have a fiduciary responsibility to get a financial outcome to investors - which I have too, and which I take super seriously. But the way I’m going about building the business is possibly atypical, and I had to figure that out for myself. As founders, we’re always chasing the destination. It’s also important to appreciate the journey. And sometimes, the journey itself is enough.

Whoever wrote this Secret VC article: I adore you. There are some absolutely excellent points that every Founder, Angel Investor, and VC in the Midwest would do well to read! Some key items: 💡 Pre-seed can absolutely be pre-revenue <-- Love to hear it! 💡 There are some VERY good takes on the angel investing environment in the Midwest. "Good angels literally write their checks on a vibe" 💡 The "closet bankers" line is fantastic. Although while I agree that VCs aren't, there are certainly plenty of reasons why founders may feel that way.... 💡 Multi-year projections in a Seed pitch deck don't make sense. <-- 1000% agree here. It's all a guessing game early on and makes no sense to me. I've taken flak for that before but it's freaking true. 💡 Founders should diligence their investors as well <-- YES PLEASE! Love when I hear about this and it's absolutely a signal that the founder knows what they're doing. 💡 It's not "us vs them". It's "us vs entropy" 💡 There's also the reality that Midwest founders may also need to raise from out-of-state investors (and how that's not a bad thing). Personally, I'm very much looking forward to the continued shift here with more angel investors writing more checks, more early-stage capital, and more large checks at later stages. Lots of room to grow... Philippe V. and the team at StartMidwest have absolutely hit it out of the park with this series. Extremely informative and what a *great* way to get a lens into how the VC world operates here in the Midwest, and how to navigate it the right way. Take 5 minutes to read this today and share your thoughts: https://lnkd.in/ed8FwbeK

The right VCs are out there, you just need to find the ones who really get you. As a founder, I quickly realized not every VC is the right fit. Most didn’t pass because of geography, not because my unit economics were off. And that’s okay. It just meant I needed to focus on the investors who could actually help. Here’s who wrote checks and moved things forward: → Angels who’d already invested cross-border and understood the game → Ex-founders who cared about CAC:LTV, not your passport → Operators who knew global GTM and didn’t need a Bay Area address These investors moved fast. Smaller checks, yes, but wired in weeks, not quarters, and opened doors institutional funds never would. You don’t need 100 “thesis-fit” VCs to say yes. You need 10 believers who got it, and they changed everything. My simple advice: Qualify investors as much as they qualify you. Look for those with cross-border experience, ask about timelines upfront, and focus on the people who can actually help you grow. The right investors don’t just fund you, they open doors, share knowledge, and believe in your vision, no matter where you’re from. How do you figure out if an investor is worth your time? #funding #founderlesson #startup #globalvc #vc

The best investors aren’t sitting on boards. They’re sitting on battle scars. A few years ago, I used to think raising from a big VC was the goal. Big name. Big logo. Big validation. Now I see it differently. The best investors I’ve worked with aren’t in the biggest funds. They’re the ones who’ve actually built. They’ve hired badly, shipped late, sold early, burned cash, fixed it and somehow built again. They know what it feels like to run out of time, money, or belief because they’ve been there. And that shows up in how they back founders. Less theory. More empathy. Less “update decks.” More “let’s fix this together.” Operator-led funds, solo GPs, micro funds. They’re building real momentum for a reason. They move faster. They stay closer. They care more. And because the landscape is shifting, relationships are becoming the real differentiator. Money is money. But access, trust, and credibility come from the relationships you build before you need them. The founder who builds genuine relationships early will raise faster and smarter than the one who builds a perfect deck late. If you’re fundraising right now, remember: You’re not just choosing investors. You’re choosing operators who get it, and people you’ll be texting at 11pm when it’s all on fire. Founders or VCs agree.

Waiting on a VC response can feel like being stuck in limbo. In a recent post, Kera DeMars of Hustle Fund breaks down why VCs sometimes drag their feet and how founders can nudge them toward a decision. A few things Kera hits on: — Why VCs take time to respond — Good & bad signs from VCs — The art of nudging potential investors Check out the full blog here: https://vsbl.io/4osxQMJ

Investors bring more than money, they bring an agenda, a timeline, and expectations shaped by their own stakeholders. Founders who understand this dynamic gain an edge in choosing the right kind of capital and setting the tone for the relationship.   Investors can be separated into different groups including angel investors, venture capital firms, and family offices. Each has a different incentive model that shapes their behavior after they invest.   • Angel Investors typically invest their own money, often driven by relationships or belief in a founder. Their incentives are usually more flexible, they’re often more patient, emotionally invested, and founder-friendly. Their capital can be great for early validation and advice.   • VC Firms manage money on behalf of Limited Partners (LPs). That means they’re not just betting on you but they’re accountable to others. Their goal is to deliver a return across their entire portfolio, not necessarily from every company   • Family Offices usually play the long game. They might be motivated by diversification, market positioning, or learning opportunities. For example, an investor might want access to your technology or insight into your customer base and not just financial return. That’s not necessarily bad, it just changes how you evaluate success together.   When you understand their incentive model, you can tailor your communication and expectations. For instance, if a fund needs big exits to return capital to LPs, frame your growth story in terms of market dominance and scale potential. If a family office values stable, long-term returns, emphasize defensibility and sustainable unit economics.   Ultimately, investor alignment isn’t all about whether they like your pitch, but it’s also about whether your business model fits their fund’s internal logic. The most successful founders don’t just take money; they choose it strategically from investors whose timelines, pressures, and incentives are compatible with how they plan to build their company.   Learn more: https://lnkd.in/gsvQySnq   #HarmoniousFundAdmin #Founders #Fundraising #HarmoniousFounders

📣 365 Capital Closes Second Buyout Fund at €255 Million, Strengthening Dutch Lower Mid-Market Strategy - 365 Capital, an Amsterdam-based private equity firm focused on the Dutch lower mid-market, announces the final close of its second buyout fund, 365 Capital Fund II, at €255 million in October 2025, exceeding its target. - The first platform investment of Fund II was completed earlier in 2025. - Strong backing comes from returning and new investors, including local institutional LPs, family offices, and entrepreneurs. - Fund II follows approximately four and a half years after Fund I’s final close in April 2021, which raised €165 million. - Fund I has built a portfolio spanning industrial manufacturing, business services, software, education, and consumer goods. - Fund II continues Fund I’s strategy: combining local deal access, disciplined underwriting, and hands-on partnerships with founders and management teams. - The goal is to create long-term, sustainable value by accelerating growth and optimizing profitability. - Targets majority investments in founder- and management-led businesses headquartered in the Netherlands. - Equity tickets typically range between €15 million and €40 million, with a sweet spot of €20–30 million. - Focuses on partnership-driven transactions emphasizing alignment and entrepreneurial collaboration. - Often addresses management succession during the holding period to ensure sustainable leadership continuity. - Success attributed to a high-quality, ambitious team driven by intrinsic motivation and a shared commitment to excellence. - Firm culture emphasizes partnership, energy, and fun as essential elements of long-term success. - This mindset extends to interactions with management teams, advisors, and long-term partners. Managing Partner: Boudewijn Molenaar and and partners: Reinaert Molenaar, Hayo van Houten, Steven Albers.

I wonder if the momentum behind 365 Capital’s €255 million Fund II—coming just a few years after its €165 million debut fund—signals a broader strengthening in Dutch lower mid-market buyout demand, especially for founder-led businesses seeking hands-on value creation partnerships. #PrivateEquity #MiddleMarket #Fundraising

Roelof Botha just called venture “return-free risk.” He’s not being dramatic. He’s doing math. $150B flows into VC annually. Billion-dollar exits that actually return capital? We get maybe twenty. MAYBE. The equation is broken. And Roelef is right to sound the alarm bells. At current fund sizes, the system would need dozens of huge wins every year to make LP portfolios pencil out. Let’s be honest….thats just not gonna happen, not at a level necessary for the returns promised. That means the asset class itself is under strain: → LPs chase exposure that can’t produce enough exits → GPs manage ballooning funds built on momentum, not multiples → Founders absorb the cost — longer timelines, harsher dilution, and a market where “caution” is really fear of negative DPI When the exit window narrows, VC stops being venture. It starts behaving like structured credit in hoodies. Three signals to track: For founders: - Fund cycles are compressing. Hold periods are stretching. - Most Series B rounds are bridges disguised as growth. - Back investors who can manufacture exits — not just chase them. For LPs: - Back managers who can create liquidity, not just mark up valuations. - Dry powder isn’t leverage when the pipeline is clogged. For everyone deploying? The math will correct. It always does. What are you seeing in your portfolio or pipeline? Are exits manufacturing themselves — or being manufactured? #VentureCapital #LPs #Founders #CapitalMarkets #PrivateEquity #VCMath #Liquidity #StartupFunding #DPI #VentureReturns