Raising capital is often the most grueling phase of a startup’s lifecycle. It requires a distinct shift in mindset – from product builder to visionary seller. But for many founders, the gap between thinking you are ready and actually being investor-ready is filled with painful rejections and missed opportunities.
We asked over 45 business owners and founders a simple but critical question: “What is one fundraising lesson you learned the hard way, and what would you tell founders preparing for their first pitch?”
Their answers reveal that successful fundraising isn’t just about a great idea; it’s about financial discipline, narrative clarity, and the resilience to handle rejection. Whether you are prepping for a seed round or seeking expansion capital, here is the ultimate guide to fundraising, directly from the trenches.
1. Numbers Over Enthusiasm: Know Your Metrics
The most common pitfall for early-stage founders is relying on passion to mask a lack of financial data. Investors invest in systems, not just dreams.
Brandon Leibowitz, Owner, SEO Optimizers
“One fundraising lesson I learned the hard way is that enthusiasm doesn’t replace preparation. Early on, I walked into investor meetings thinking my passion for digital marketing and the success of my early clients would be enough to win them over. What I didn’t realize was that investors don’t just buy into vision – they buy into systems, numbers, and scalability. During one pitch, an investor asked for specific CAC-to-LTV ratios, and I didn’t have a clear answer. That meeting ended fast, but it taught me to back every story with hard data.
For founders preparing for their first pitch, my advice is simple: know your numbers like you know your product. Investors hear dozens of ideas a week, but the ones who stand out demonstrate financial discipline and a roadmap to growth.”
Ibrahim Alnabelsi, VP – New Ventures, Prezlab
“Investors don’t just care about your user growth. They want to see the unit economics. We learned this after focusing only on user counts and getting nowhere. Once we started showing our CAC payback periods and gross margins, the conversations got way better. If you’re prepping for your first pitch, just show your real numbers and explain how your SaaS model actually makes money as it grows.”
Justin Carpenter, Founder, Jacksonville Maids
“Here’s what pitching Jacksonville Maids taught me: investors worry about cash flow in service businesses. Having a payroll runway, six to nine months worth, changed the entire conversation. It showed we weren’t naive about the real risks. So my advice to first-time founders is this: prove you can survive the slow months on your own before you ever ask anyone for money.”
Carlos Nasillo, CEO, Riderly
“I discovered early on that fundraising isn’t selling your idea, it’s demonstrating to investors that you have deep ANSWERS to your numbers… In our first round, I focused too much on the emotional story… Investors liked the vision, but they wanted to see proof we could grow responsibly.
To founders pitching for the first time: Think of your pitch deck like a MAP, not a movie trailer. Demonstrate how you will go from A to B, make realistic assumptions and show you know something about the road.”
Tom Terronez, CEO, Medix Dental IT
“Here’s the brutal lesson I learned. Your tech doesn’t matter if it’s all you have. Investors want to see numbers. When I first pitched, they kept asking about our customer retention rate and wanted proof of HIPAA compliance… Once I showed them the actual data, the hard numbers, they started listening for real.”
2. The Power of Storytelling & Human Connection
Data is the foundation, but the story is the hook. Founders who can articulate the “why” behind the business often outperform those who only explain the “how.”
Jason Velie, Owner, Cape Fear Cash Offer
“I learned the hard way that investors don’t just invest in numbers on a spreadsheet… I walked into my first pitches with a perfect financial case, like I was managing a trust fund, but I failed to connect it to our mission… My advice for your first pitch is to remember that investors are backing a founder, not just a business plan – show them your financial acumen, but then tell the human story of the problem you solve to prove you’re the right person to steward their investment.”
Max Marchione, Co-Founder, Superpower
“I found that investors don’t remember page 17 of your deck, but they do remember a good story about why you’re doing this thing. When I stopped listing features and started sharing my personal reasons, meetings felt completely different… My advice? Tell them why it matters to you, then just handle the hard questions.”
David Cornado, Partner, French Teachers Association of Hong Kong
“Here’s a fundraising mistake I made. I spent weeks on slick technical slides, only to find investors leaning in when I just told a simple story about my research. They cared more about the problem than my data… The confidence comes when you stop performing and just talk about what you know is true.”
Ryan Brown, CTO, Search Party
“Man, I learned this the hard way with Search Party. I went into investor meetings explaining all the technical bells and whistles, and their eyes would glaze over. Then I started with why this matters right now, and suddenly they were leaning in… Practice your pitch on your neighbor or your cousin – anyone who doesn’t know your industry. They’ll tell you exactly where you’re losing them.”
Niclas Schlopsna, Managing Partner, spectup
“One of the hardest lessons I learned early in fundraising was that investor readiness isn’t just about having a polished deck, it’s about timing and narrative alignment… My advice to founders preparing for their first pitch is simple: don’t assume data alone will convince. Spend time crafting the story around your numbers, anticipate tough questions, and practice articulating why your solution matters today and tomorrow.”
Will Melton, CEO, Xponent21
“My biggest fundraising mistake? I spent twenty minutes talking to an investor about our algorithm’s details. You could see their eyes glaze over. I completely forgot to explain why we were even doing this. Now I know it’s not about the product, it’s about whether they get you. Tell your story, show your excitement. That connection sticks with them way more than any stats.”
3. Clarity Breeds Confidence: Keep It Simple
Complexity is the enemy of funding. If an investor cannot understand your business model in the first few minutes, you have likely already lost them.
Max Shak, Founder/CEO, nerD AI
“I learned a lesson the hard way… investors don’t just invest in your idea, they invest in your clarity. I remember walking into one of my first serious meetings convinced that passion and a big vision would carry the room. Instead, the investor stopped me halfway through and said, very politely, ‘Max, I still don’t understand the problem you’re solving.’…
If I could give one piece of advice to a founder preparing for their first pitch, it’s this: rehearse explaining your business without slides, prompts, or jargon. Just a straightforward conversation, the same way you’d explain it to someone over coffee.”
Jeremy Schooler, Founder, Kitsap Home Pro
“I learned the hard way that overcomplicating your pitch can sink your chances fast. Early on, I tried to explain every angle of construction, real estate, and investment strategy in one sitting – and I lost people halfway through. Now, I tell founders to cut out 80% of the fluff and lead with one clear, compelling story that shows how you make money and why you’re the right person to do it; clarity beats complexity every time.”
Ed Ovenden, Co-founder & Design Director, The Lad Collective
“Raising capital taught me that passion and polish are not enough – you must show FOCUS… I was pitching everything – new SKUs, going global, wellness initiatives – when all investors wanted was proof that we could scale one core product profitably. To first-time founders, it’s clarity that is your greatest currency.”
Lord Robert Newborough, Owner, Rhug Organic Farm & Rhug Ltd
“The hardest truth came when we lost funding due to complexity. Overexplaining clouded the simplicity that made our mission compelling. Investors need clarity within seconds, not paragraphs of context… My advice is to craft a message anyone can repeat. Simplicity multiplies advocacy faster than elaborate persuasion.”
4. Betting on the Team: Why “Who” Matters More Than “What”
Investors know that products pivot and markets change, but the team remains. You must prove you are the right people to execute the vision.
Sreekrishnaa Srikanthan, Head of Growth, Finofo
“One big thing I learned from fundraising is that the team matters more than the idea. In early rounds, investors would spend five minutes on the product and then thirty minutes on our backgrounds. They wanted to know why we were the people who could actually build it. So for your first pitch, focus on telling your own story. Explain why this group of you is the one that can get it done.”
Yarden Morgan, Director of Growth, Lusha
“If you’re fundraising, know that investors are looking at your team, not just your idea. We stopped just talking about our backgrounds and started showing how we work together on tough problems. That’s what they actually care about. So don’t just say you’re a great team. Tell them a real story about how you collaborated. That’s what sticks.”
Vlad Ivanov, CEO, WordsAtScale
“My biggest mistake? Selling the idea, not the team. Investors might like your plan, but they’re betting on the people who can actually pull it off. We changed our pitch to show our track record and how we worked together. It made a huge difference. Suddenly the conversation shifted from ‘if’ to ‘how.’ They started to believe in us, not just our slides.”
Daniel Hebert, Founder, yourLumira by SalesMVP Lab Inc
“I learned a tough fundraising lesson the hard way. I walked into a pitch with just product specs and it completely flopped… The room only came alive when I started talking about my previous company that I’d built and sold. Investors aren’t betting on your idea, they’re betting on you… So dig up your stories about how you solved real problems.”
Bennett Maxwell, CEO, Franchise KI
“Building Dirty Dough taught me this: stop obsessing over your pitch deck. My partners and I once pulled an all-nighter to fix a huge problem right before an investor meeting. We got the funding. They didn’t care about the slides, they cared that we didn’t fall apart. Get the right team first, everything else is secondary.”
5. Traction Speaks Louder Than Words
Don’t just promise future results; show what you have already achieved. Whether it’s a pilot program, early revenue, or a completed project, evidence reduces risk.
Yoan Amselem, Managing Director, German Cultural Association of Hong Kong
“I learned early on that investors don’t buy passion, they buy proof. My pitches about our education mission went nowhere until I started showing actual numbers and student success stories… If you’re getting ready to pitch, skip the vision speech for a minute and make a one-pager with your real results. That’s what gets attention.”
Alvin Poh, Chairman, CLDY.com Pte Ltd
“I learned my fundraising lesson the hard way. I thought investors wanted to hear about big future plans, but they actually cared about what we had already done. Solving one real, small problem was worth more than talking about ten imaginary big ones. So show them what you’ve finished. Investors respond to action, not just talk.”
Ryan Dosenberry, CEO, Crushing REI
“Here’s what I learned: build something real before you talk to investors. I started my own academy and wrote down case studies, which gave my pitches actual weight… If you’re a first-time founder, don’t just say you’re an expert. Show them. A project, some case studies, or a course changes the whole conversation.”
Brian Tetreault, Co-Founder, Kitching & Co. Dirtworx
“I blew my first pitch. I bragged about how many deals we signed, but investors only cared about one thing: money that comes in reliably every year. I should have led with our long-term municipal contracts… For other founders, highlight your existing relationships first. It proves you’re not going to disappear overnight.”
Daniela Pedroza, CEO and Co-founder, Siana Marketing
“I learned a tough fundraising lesson early on. Investors care way more about predictable results than creative potential. The second we pre-sold a few campaigns and landed a couple of known clients, the whole conversation shifted… So my advice to founders is simple: lock down some early clients or a clear win before you pitch.”
Graham Bennett, COO, Bennett Awards
“I used to think investors wanted a big idea. Turns out, they just want to see you can actually sell things more than once… once I started showing them the small but steady client wins, the whole conversation shifted. It got real. Just walk them through your pipeline. Any real deal, no matter how tiny, beats a fancy pitch deck every time.”
John Cheng, CEO, PlayAbly.AI
“I learned the hard way that investors don’t care about your slides, they care about your track record. I remember one pitch where I spent weeks perfecting the deck, but they only wanted to talk about our past product launches and real numbers. If you’re a first-time founder, focus on getting things done and showing results.”
Karl Threadgold, Managing Director, Threadgold Consulting
“My biggest lesson? Don’t hide your customers. Early on, I pitched my SaaS business with just metrics. Once I added testimonials from longtime clients, investor interest suddenly picked up… If you’re preparing a pitch, getting proof from happy users is way more powerful than just showing growth charts.”
Brooks Humphreys, Founder, 614 HomeBuyers
“I thought my real estate track record would speak for itself, but investors wanted a clear story about the current opportunity, not just past wins… Once we stopped talking big-picture vision and focused our pitch deck on actual deals, the conversations got way easier.”
Christopher Pappas, Founder, eLearning Industry Inc
“Early on, I confused traction with transformation. I thought early user numbers were enough to convince investors but they wanted to see growth patterns and not just snapshots. The hard truth was that short-term results rarely justify long-term belief… My advice is to measure what matters and focus on how each milestone supports your vision.”
6. Relationships & Trust: It’s Not Just Transactional
Fundraising is ultimately a people business. Building genuine relationships and trust often yields better results than a cold pitch.
Lawrence Irby, President, Bay Area House Buyer
“I learned the hard way that in real estate, your relationships often matter more than the numbers on a spreadsheet. I’ve seen solid deals stall because we didn’t build actual trust with investors… My advice is to listen more than you talk. That’s what gets them to write the check for the next deal too.”
Cyrus Partow, CEO, ShipTheDeal
“Fundraising showed me something important – numbers and product features don’t close deals. People do. When I actually got to know investors before asking for money, follow-up meetings happened way faster. I’d tell founders to practice having real conversations instead of perfect pitches… being yourself actually works better than having a script memorized.”
Carl Fanaro, President, NOLA Buys Houses
“I learned a fundraising lesson the hard way: your relationships matter more than your numbers. I used to focus on spreadsheets, but investors cared more about my network… Once I showed them those actual partnerships, they got comfortable with our ability to get things done.”
Mike Wall, Founder/CEO, We Buy Gulf Coast Houses
“I used to just stare at spreadsheets, thinking that’s what private lenders wanted to see. I was wrong. I should have been calling them, updating them on how projects were actually going, the good and the bad… That’s how they know you get it.”
7. Know Your Audience: Research & Alignment
Pitching to the wrong investor is a waste of time. Alignment in mission, stage, and sector is critical.
Kevin Clancy, President, American Funding Group
“I learned early on that trying to pitch investors without truly understanding their investment criteria was like trying to sell a second lien note to someone who only buys first position mortgages… My advice to founders is simple: do your homework on each investor before you walk in that room, understand exactly what they’re looking for, and tailor your pitch to show how your opportunity fits their specific investment thesis.”
Matthias Woggon, CEO & Co-founder, eyefactive
“One key fundraising lesson I learned the hard way is the importance of aligning your pitch with the specific interests and goals of your investors. Early on, I made the mistake of delivering a generic pitch… My advice to founders is simple: do your homework, know your audience, and ensure your pitch demonstrates exactly how your solution aligns with their investment thesis.”
Hans Graubard, COO & Cofounder, Happy V
“Our team dedicated multiple months to pursuing investors who showed interest in our presentation yet failed to demonstrate genuine interest in our specific market segment or development level… The process of fundraising requires more than presentation skills because it demands founders to determine if potential investors match their needs.”
Julia Pukhalskaia, CEO, Mermaid Way
“The experience showed me that financial support does not guarantee someone will support my mission. I accepted funding from an investor who appreciated my brand design but failed to grasp its core essence… Your first pitch preparation requires you to define your purpose beyond the presentation materials.”
Igor Golovko, Developer, Founder, TwinCore
“The team dedicated excessive time to deck development instead of establishing investor qualification at an early stage. Our efforts to present to inappropriate investors resulted in delayed progress… Our team now dedicates time to achieve alignment with potential investors before their initial meeting by verifying their interest in our sector and stage.”
Lewis Hammond, Marketing Director, Bright Future Home Buyers
“I learned early on that not demonstrating a deep understanding of my market’s specific challenges cost me investor trust… My advice to founders is this: be the expert in your room. Analyze how your proposal fits against hyperlocal trends… so investors see you’ve mapped each risk and opportunity.”
8. Reality Checks: Honesty, Risk, and “Nos”
Investors appreciate founders who are realistic about risks. Pretending everything is perfect is a red flag. Furthermore, hearing “no” is part of the process.
JP Moses, President & Director of Content Awesomely, Awesomely
“I made a huge mistake in my first funding round: I pretended nothing could go wrong. Investors saw right through it. Now I do the opposite. I tell them everything that might break and what our B plan is. That actually makes them more comfortable writing a check.”
Brandon Brown, CEO, Search Party
“I got my butt kicked learning that ‘no’ is normal. The first round, we probably heard ‘no’ thirty times. But those tough audiences? They were the best teachers… So if you’re prepping for your first pitch, expect pushback. Every meeting just sharpens you for the next one.”
Rakesh Kalra, Founder and CEO, UrbanPro Tutor Jobs
“I used to bluff my way through pitches when hit with a tough question, my nerves would just take over. But then I tried something different. I just said, ‘I don’t know that, but here’s how we’ll find out.’ It worked. The investors seemed relieved. So my advice is, stop worrying about having all the answers. Show them your thought process instead.”
Chris Lowe, CEO, Next Step House Buyers
“I learned a fundraising lesson the hard way. Investors don’t actually care about your property value, they want to know how you handle it when things go wrong… Now I tell the story about the leaky roof we found during inspection and still closed on time. That’s what puts them at ease. They want to see you’ve messed up and fixed it, not that you’re perfect.”
Runbo Li, CEO, Magic Hour
“Fundraising sucked because of all the rejection. Then someone at YC told me those ‘no’s meant our idea was getting out there. So we started writing down every tough question we got and rewrote our pitch. The next round of conversations was completely different. The investors who poke holes in your idea are doing you a favor.”
Josiah Lipsmeyer, Founder, Plasthetix Plastic Surgery Marketing
“The biggest lesson I learned is that a great pitch doesn’t guarantee a check. We wasted weeks early on chasing people we were sure would close, only to find they were just stalling. My advice? Never stop talking to new potential investors. Don’t pin your hopes on one meeting that goes well. It probably isn’t real.”
9. Leveraging Specialized Knowledge & Operations
Sometimes, your edge isn’t the product itself, but how you operate it or your unique access to the market.
Lisa Martinez, Founder, TX Cash Home Buyers
“I learned a tough lesson fundraising. Capital alone doesn’t make you stand out. What changed everything for me was getting access to off-market foreclosures and probate deals that other people couldn’t find… If you’re getting ready for your first pitch, focus on how you source your deals. That’s what they actually want to bet on.”
Tom OBrien, CEO, DRM Healthcare
“The first lesson I learned shows that investors value business model sustainability more than they do new concepts… Our presentation of onboarding procedures and CQC success rates and staffing model profitability margins brought about an instant change in investor interest. First-time founders… must demonstrate to investors that you would use their funding to create a safe patient environment while following all regulations.”
Phil Cartwright, Head of Business Development, Octopus International Business Services Ltd
“The process of securing early capital taught us to understand that investors focus more on their own evaluation methods than on our company’s actual value… The team made a breakthrough when they adopted underwriter thinking to evaluate their worst possible situation… Investors seek to witness how your organization and team members handle breakdowns in legal operations and reputation management.”
Ryan Hall, Founder & President, Coastal NC Cash Offer
“One hard lesson I learned early… was underestimating how crucial my hyperlocal track record was to investor confidence… To founders I’d say: lead with what makes your execution uniquely proven in your backyard, whether it’s neighborhood-specific data or relationships you’ve cultivated for decades.”
Bennett Heyn, Founder, Backlinker AI
“I used to spend way too much time perfecting the product. Then I realized investors don’t care as much about that. They want to know if your team can actually get things done and change course when needed. What worked for us was being open about our past pivots and small wins during the pitch.”
Gene Martin, Founder, Martin Legacy Holdings
“I learned that trying to fundraise while simultaneously running operations was a recipe for burnout and missed opportunities… My advice is to carve out dedicated, uninterrupted time blocks specifically for fundraising and treat it like its own full-time job during that season.”
Sandro Kratz, Founder, Tutorbase
“Screwing up Tutorbase’s first fundraise taught me how much timing matters. Our product was a mess but I went for it anyway… My hard-won lesson? Get real user feedback before you talk about your big idea. The conversation goes so much better when you have actual numbers to back you up.”
Zack Moorin, Founder, Zack Buys Houses
“Fundraising is a lesson in preparedness, focus and resilience. Investors love a good, simple narrative about the problem that needs to be solved… Founders should be also have the expectation of rejection and see it as a chance to sharpen one’s approach.”
Nir Appelton, CEO, The CEO Creative
“One fundraising lesson I learned painfully is that founders often overestimate what investors care about… The lesson: lead with the problem and your solution, not metrics first. Also, don’t try to be perfect. Investors want honesty and realism, not a flawless fairy tale.”
Lord Robert Newborough, Founder/Owner, Rhug Wild Beauty
“I once faced rejection from investors who believed that sustainability would slow down profits… I focused on showing that responsible practices could drive both purpose and performance and not hinder them… Every no helps refine the path toward the right yes, one that supports integrity and innovation equally.”
Conclusion
If there is one thread connecting these diverse experiences, it is this: Preparation breeds confidence. Whether it is knowing your unit economics, researching your investor’s thesis, or simplifying your narrative, the work you do before the pitch is just as important as the pitch itself.
Fundraising is a skill that is learned through friction. As these 45+ founders have shown, every rejection is data, and every “hard lesson” is a stepping stone to the capital you need to scale.
Ready to pitch? Start by auditing your current deck against these lessons. Are you hiding your team? Is your story too complex? Do you know your CAC/LTV ratio? Fix these gaps, and you will walk into that room not just as a founder, but as an investment opportunity they can’t afford to miss.