Tips for Recognizing Pitching Mistakes

We’ve received 7000+ seed pitch decks over the last decade. Here are the most common mistakes we see: 1. Not putting the team slide upfront. Quality of team is a key signal at seed. 2. Missing market sizing calculations. Don’t just quote a TAM – derive it from scratch. 3. Don’t mix advisors and founders on the same slide. And be clear with who is FT and who isn’t. 4. Not referencing the competitive landscape. A market map shows you’ve done your homework. Also, “We have no competitors” makes investors nervous. 5. Be transparent on the traction slide. How many of your clients are paying vs non-paying? Better to say you have zero ARR than stretch the truth. 6. How much are you raising? Decks that don’t mention the raise size are half as likely to get a response. 7. Be clear on valuation. Every investor will ask. By calling it out upfront you’ll filter out a lot of noise. 

Most startup pitches lose the room immediately and no one tells you why. Why not? Most advisors never took a debate class, skipped sales training, and slept through the public speaking workshop. Let me drop the startup buzzwords to explain how we know your startup is going to fail just because of how you pitch. 1. Catch-22 statements: “We can’t get customers without funding and can’t get funding without customers.” 2. Selling instead of pitching: “This is revolutionary and guaranteed ROI,” before anyone understands the problem. 3. Ad hominem attacks: “Legacy players are stupid, slow, and don’t care.” 4. Red herrings: Flashing logos, followers, or demos instead of explaining growth or advantage. 5. Ignoring competition: “We don’t have competitors.” 6. Straw man arguments: “Everyone just uses spreadsheets because they don’t know better.” 7. False dilemmas: “Either you adopt this now or you’ll fall behind.” 8. Slippery slope claims: “If this isn’t built immediately, the market is gone forever.” 9. Appeal to authority: “Top advisors are interested,” with no explanation why that matters. 10. Circular reasoning: “Customers choose us because we’re better… we know we’re better because customers choose us.” 11. Hasty generalization: “Three users loved it, so the market is massive.” 12. Post hoc causation: “Revenue went up after the feature launch, so the feature caused growth.” Pitch work isn't to get you to pitch properly to investors. It's working on your thinking. I wrote how to spot these, why they signal unmanaged risk, and how to fix them, because making these mistakes doesn’t just weaken your pitch, it causes you to fail before you start. A startup pitch isn’t a sales pitch. No one is buying. We’re deciding whether your idea creates enough value to justify our time, credibility, and risk. If you’ve ever wondered why doors don’t open, intros don’t happen, or advisors disengage, this is why.

13 Common Mistakes to Avoid in Your Startup Pitch Yesterday, I attended presentations of seven startup pitches. Although each proposal displayed unique strengths and several were notably compelling, prevalent weaknesses undermined their overall effectiveness. Here are thirteen mistakes to avoid: 1. No Storytelling: Craft a narrative to make your venture memorable and relatable. 2. Not Tailoring the Content: Customize your pitch to address your audience's specific knowledge and concerns. 3. Lack of Eye Contact: To make your pitch feel personal, engage with your audience, not your notes. 4. Starting with the Value Proposition: You should begin with the problem you are solving to make your solution easier to understand. 5. Unclear statements: use numbers like "We are 30% less expensive" for clarity instead of "We are cheaper." 6. Overloading Slides: To maintain clarity, keep slides concise, with no more than 50 words each. 7. Poor Visual Execution: Ensure slides are not cropped and fonts are legible to avoid distractions. 8. Complex Delivery: Use a single, well-prepared speaker to keep the presentation dynamic and easy to digest. 9. Avoid Live Demos: Opt for a recorded demo to prevent the risks of live technical glitches. 10. Failing to Explain the Market Size: Use simple visuals like bar charts to communicate the opportunity clearly. 11. Ignoring the Importance of Full Names: For professionalism and connectivity, include full names on the team slide. 12. Unrealistic Financial Expectations: Set realistic timelines for breaking even or achieving payback. It's not going to happen in 3 years. 13. Omitting a Clear Ask: To leverage the audience, end with a specific request for capital, clients, or talent. And keep in mind what Jean de La Rochebrochard said: "Knowledge = Trust, Execution = Credibility, Vision = Desire"

I've watched 1,000+ sales pitches fail for the exact same reason. After coaching some of the best AEs in tech, I discovered the real problem isn't what you're saying—it's the entire framework you're using. Most companies create pitch decks that brag about themselves. This NEVER works. Customers don't care about your products. They care about their problems. For years, I've taught my private coaching clients a framework that's completely transformed their close rates. I call it the 5 P's of Pitching: 1/ PROBLEM What high-level business problem do you solve? This must matter to executives—not technical teams. If you sell CRM, your problem isn't "manual data entry." It's "rep underperformance" or "missed forecasts." 2/ PRIMARY REASON Why does the problem exist? Nail the root cause. "Leadership has poor visibility to pipeline and no accurate way to predict which deals will close." Articulating this builds immediate credibility. You speak their language. 3/ PAIN What metrics are suffering because of this problem? Missed forecasts lead to plummeting stock prices, revenue shortfalls, and sales layoffs. This is where you make it personal for the decision maker. 4/ PROMISE How does your solution address the PRIMARY REASON for the problem? "Our AI-driven forecasting prevents inaccurate manual forecasting and low deal visibility." Don't list features. Focus on solving their specific challenge. 5/ PAYOFF What metrics will improve when you solve their problem? For CRM: improved quota attainment, rep productivity, and accurate forecasting—all driving revenue and profitability. The 5 P's framework works because it's centered on the customer, not on your product. The best part? It takes 15 minutes to build and dramatically increases your close rate. If you want a copy of the 5P's template I use with my clients, comment TEMPLATE below.

Insights from a CFO: Why Salespeople Win or Lose Deals Selling to the C-suite isn’t for the faint of heart. As a CFO for over 25 years, I’ve seen pitches that were brilliant and others that were, frankly, baffling. This article shares what separates pitches that succeed from those that fall flat. 1. Trust: The Unsexy but Critical Ingredient Trust is the foundation of every deal. C-suite execs can sense insincerity quickly. Be honest about risks as well as rewards and explain how you’ll mitigate them. According to Gartner, 89% of executives say trust is the key factor in deal-making. PRO TIP Address a specific and recognized challenge right away. It shows you've done your homework. EXAMPLE “I noticed you’ve increased spending on supply chain optimization. We’ve helped similar companies reduce such costs by 10-20%.” RED FLAG Dodging requests for references or giving vague replies is a deal-breaker. 2. Speak CFO: Money Talks, Buzzwords Walk CFOs care about financial impact, not buzzwords. Pitches emphasizing ROI have a 32% higher success rate. PRO TIP Lead with numbers—ROI, cost savings, or revenue potential. EXAMPLE “Our solution can cut your cloud storage costs by 30% annually,” is more compelling than vague promises of transformation. RED FLAG Overpromising ROI without solid data raises immediate doubts. 3. Don’t Just Sell—Prescribe The best salespeople diagnose issues and prescribe actionable solutions. PRO TIP Ask questions that reveal underlying problems, then position your solution as the fix. EXAMPLE “Your logistics costs have grown faster than revenue. Here’s how we fixed that for similar firms.” RED FLAG Overemphasis on features instead of solving specific problems is a misstep. 4. Speak Our Language If you sound like a techie or scripted, you’ve already lost. Executives are five times more likely to engage when you speak their language. PRO TIP Share relevant stories or lessons from past failures to build credibility. EXAMPLE “You increased R&D spend by 20% last quarter—are you prioritizing innovation or trying to manage to your margin?” RED FLAG Excessive jargon or acronyms is a quick way to lose interest. 5. Follow-Up: The Forgotten Art Deals aren’t closed in meetings—they’re closed in the follow-up. Following up within 24 hours can boost close rates by 60%. PRO TIP Conclude meetings with clear next steps, timelines, and follow-up dates. EXAMPLE A customized ROI analysis sent within 24 hours led us to a signed deal two weeks later. RED FLAG Generic or delayed follow-up suggests a lack of genuine interest. The Bottom Line Selling to the C-suite is about trust, authenticity, and delivering measurable business outcomes. Master these elements, and you’ll build lasting relationships that go beyond a single deal. Anything to add? #SalesLeaders #CSuite #StrategicAccounts #SellingtoExecutives #Executives #CXOs #CEOs #CFOs #ChiefRevenueOfficers #SalesEnablement #LearningandDevelopment #CorporateUniversities

I've had the pleasure of working with hundreds of #freelance writers on thousands of stories for the past eight years at Business Insider — and I’ve read more pitches than I could ever count. 📫 Over time, I've noticed there are three common things that can hold a pitch back from being truly great... ⭐ There's no clear angle or purpose You went to Paris for the first time...and? You retired at 50...and? You moved from Canada to Texas a decade ago with your kids...and? A strong pitch shouldn’t leave an editor wondering: Why does this matter? What angle do you want to write about? What’s the takeaway? If you can answer those questions upfront and weave them into your pitch, great! It's also helpful to write a mock headline (or two) to pair with your pitch. Some editors like a “Why this matters” section, but ideally, your pitch makes that clear without you needing to spell it out separately. (And a quick note: If you're pitching me, skip the "Why this is a good fit for Business Insider" section. Understanding our audience and helping shape stories for them is part of my job. Although this won't hurt your pitch, these sections have never, ever convinced me to accept one. Save yourself some time!) ⭐ There's no voice If your pitch is generic and reads like something any person (or AI) could've written, editors can worry your draft will feel the same way. On the other hand, seeing a writer's voice and style early on can help a pitch really stand out. I've said yes to stories I wasn't 100% sure about because the writer had such a compelling voice (...and lots of great details in their pitch). Let your personality come through in your pitches and write them in a style that's similar to how you'd write the final piece! ⭐ Key details are missing If you’re pitching a story on surprises or disappointments, tell me what they are. If it’s about a trip or experience, include when it happened. If it's about the best place you ever lived, tell me where, what brought you there, and give me a few lines about why you love it. When a lot of questions are left unanswered, a pitch can get lost in the back-and-forth email shuffle or tossed to the side in favor of fully formed ones. Ultimately, when you’re competing with hundreds of other pitches, even small gaps can make a difference. I hope this is helpful to anyone #freelancing — I know pitching can feel discouraging sometimes, but I am rooting for you! #freelanceadvice

After investing in 20+ startups & helping many with fundraising, Here are 5 "NEVER-TO-DO's" for startups (investors see them as red flags) 👇 After years of fundraising & advising others, I’ve seen it all—both the wins & the blunders. Here are 5 NEVER TO DO's for founders 👇 𝟏/ 𝐂𝐥𝐚𝐢𝐦𝐢𝐧𝐠 𝐚 $𝟓𝟎 𝐛𝐢𝐥𝐥𝐢𝐨𝐧 𝐓𝐀𝐌 𝐰𝐢𝐭𝐡𝐨𝐮𝐭 𝐛𝐚𝐜𝐤𝐢𝐧𝐠 𝐢𝐭 𝐮𝐩 𝐰𝐢𝐭𝐡 𝐬𝐨𝐥𝐢𝐝 𝐝𝐚𝐭𝐚. ↳Investors will question your credibility. 💡 Solution: Be optimistic, but stay grounded in reality. Refresh your understanding of TAM, SAM, and SOM. This slide should be a box-ticker, not a "we better double down on DD" moment for the investor. 𝟐/ "𝐖𝐞’𝐥𝐥 𝐟𝐢𝐠𝐮𝐫𝐞 𝐨𝐮𝐭 𝐦𝐨𝐧𝐞𝐭𝐢𝐬𝐚𝐭𝐢𝐨𝐧 𝐥𝐚𝐭𝐞𝐫" 𝐢𝐬 𝐚 𝐝𝐞𝐚𝐥𝐛𝐫𝐞𝐚𝐤𝐞𝐫. ↳A lack of a clear revenue model is a big "no" from any investor. 💡Solution: Show investors that you’ve thought through how your business will make money. If you haven’t started monetising yet, make sure your plan to get there is thoughtful, your valuation is reasonable, and/or your data, growth & engagement are through the roof. 𝟑/ 𝐎𝐯𝐞𝐫𝐥�� 𝐜𝐨𝐦𝐩𝐥𝐞𝐱 𝐩𝐢𝐭𝐜𝐡 𝐝𝐞𝐜𝐤𝐬. ↳If it takes more than 2 min & 30 sec to understand what your company does, your deck is too complicated. 💡Solution: Keep your pitch deck clear, concise & compelling. Investors spend an average of 2.5 min looking at a deck, often from their mobile phones, so every slide should be easy to digest even on a small screen & in just a few seconds. 𝟒/ 𝐈𝐠𝐧𝐨𝐫𝐢𝐧𝐠 𝐜𝐨𝐦𝐩𝐞𝐭𝐢𝐭𝐢𝐨𝐧. ↳Investors know there’s always competition, direct or indirect. 💡Solution: Acknowledge competitors & differentiate your offering. Where you sit in terms of your competitive positioning & how you’ve analysed this can elevate you from naive to brilliant in the mind of your investor. 𝟓/ $𝟏𝟎𝟎 𝐦𝐢𝐥𝐥𝐢𝐨𝐧 𝐢𝐧 𝐫𝐞𝐯𝐞𝐧𝐮𝐞 𝐛𝐲 𝐲𝐞𝐚𝐫 𝟑 𝐰𝐢𝐭𝐡 𝐳𝐞𝐫𝐨 𝐛𝐞𝐥𝐢𝐞𝐯𝐚𝐛𝐥𝐞 𝐞𝐯𝐢𝐝𝐞𝐧𝐜𝐞. ↳Unrealistic financial projections without any data are a big "no." 💡Solution: Show realistic growth based on real data. If all you have is customer feedback, frame things around this. If you have pre-sales, extrapolate from there. Ground your projections in believable chunks building from the ground up while also staying aware of the “top-down” metrics like in Slide 1 on your TAM. 𝐁𝐎𝐍𝐔𝐒: Attention to detail is your secret weapon. 🕵️♂️ ✅ When pitching, the devil is in the details. ✅ Don’t have old dates or high version numbers. ✅ Don’t let any misspellings or grammar mistakes make your potential investor question your focus & attention. ——— Every pitch is a learning experience. Don’t take rejection personally & avoid these red flags at all costs. Still stuck and hearing "no's" consistently while raising? It might be time to ask for help - feel free to drop a DM. P.S. Share this & tag your founder friends to help them. #fundraising #investors #founders #vc #startup

Sick of hearing “no” in negotiations? These five fixes will turn rejections into wins. Understand why your negotiations fail, and gain powerful strategies to flip rejections into confident agreements. After decades of coaching global leaders through tough negotiations, I’ve learned a crucial truth: Most rejections aren’t about your offer, they’re about your negotiation approach. Here are honest lessons from my own painful negotiation mistakes, paired with clear, actionable fixes: 🔴 Mistake #1: Selling instead of solving Early in my career, I passionately pitched a partnership that was quickly rejected, it served my interests, not theirs. High stakes and embarrassment followed. ✅ Action: Never pitch without first asking clearly: “What outcomes matter most to you?” 🔴 Mistake #2: Ego over empathy Confidently proposing strict terms to demonstrate professionalism backfired when the client felt disrespected. Immediate rejection taught me, empathy beats ego every time. ✅ Action: Clearly show respect and collaboration: “Your insights are vital; let’s build this together.” 🔴 Mistake #3: Ignoring their better alternatives A major deal slipped through my fingers because I overlooked my client’s superior alternative (BATNA). My silence made my proposal irrelevant and costly. ✅ Action: Address alternatives directly: “I recognize you have other strong options; here’s why my offer uniquely benefits you.” 🔴 Mistake #4: Threatening their reputation I once had a deal collapse because accepting it would’ve undermined my counterpart’s internal credibility. A painful oversight I won’t forget. ✅ Action: Actively protect their reputation: “How can we structure this deal to enhance your internal credibility?” 🔴 Mistake #5: Losing trust Repeated rejections from a key client taught me they had lost trust due to hidden risks. Transparency became my essential tool for successful negotiations. ✅ Action: Be radically transparent: “These are the risks; let’s address them openly and together.” Rejection isn’t failure, it’s your best negotiation guide when you decode it clearly. What’s your go-to strategy for overcoming negotiation rejection? If this helped you rethink how you handle rejection don’t keep it to yourself! Repost, comment, or tag someone who needs to read this today. ♻️ 

6 mistakes I used to make on sales calls, and 5 things I do now to avoid them: 1. Chasing every deal -As a new AE, I thought I had to win every opportunity. I wish I disqualified faster. 2. Jumping to the ‘how’ before the ‘why’ -When a prospect shared the ‘what,’ I skipped to sharing how I could help... I never paused to ask why it mattered. 3. Failing to multi-thread -Early on, I thought the person on the call was the only DM. Most Mid-Market or ENT deals have 5-7 or 15+ stakeholders. Got stuck with the wrong person way too many times. 4. Avoiding tough conversations -I thought if I asked hard questions to the prospect, they would not want to engage with me.. I quickly realized that was a terrible approach & all I was doing was not getting the answers that would allow me to know what would move the deal forward. 5. Getting happy ears -No competitors? They own the budget? Music to my ears, until I goth ghosted lol.. I learned to treat those signals as red flags. 6. Winging it -I lacked intention in prep. I wasn’t asking the right questions or planning my what I wanted the outcome of the call to be throughout disco & demo calls. What I do now: 1. Prep a POV → Outbound: -Research 2–3 likely pain triggers -Build a “pain menu” for the call -When I hear the 'what,' dig into the 'why' → Inbound: -Ask why they took the call & why now -Ask “What’s driving the need for XYZ?” -If there’s no why behind the what aka pain, disqualify fast 2. Lock in next steps -Set a 15-min pre-demo prep call and a 15-min post-demo debrief. Frame the entire process upfront. 3. Get to ‘no’ fast -Friction early is better than getting ghosted later. Ask the hard questions. 4. Ditch the slides & tell better stories on discovery calls -Have 2–3 customer stories ready that paint a vision. Use your own wins if possible. 5. Layer questions naturally -Good discovery is about listening, going deeper, and truly wanting to understand what's driving their needs.. aka the 'why behind the what' Great tools help too: WINN.AI (which I use in Natoli’s Nuggets Coaching calls) helps reps avoid these mistakes with: ✅ Live AI Guidance → Guides reps with talk tracks and capturing next steps in real-time. This helps you avoid all the happy ear mistakes… IE: Forgetting to quantify pain? WINN will tell you. ✅ Real-Time Call Assistance →  acts as a live sales assistant during calls, helping reps stay focused by automatically tracking questions, objections, and action items. Imagine hearing a specific piece of feedback from a customer and having a live recap in real-time. Hopefully these tips help, especially if you're a newer seller!

Here’s a classic sales mistake. My wife, Drita, walked into a Croma showroom to buy the Samsung Galaxy S24. The salesperson treated her like she hadn’t didn’t know anything. Here’s the exchange: Salesperson: “Hi, looking for a new phone?” Drita: “I’m interested in the Galaxy S24.” The salesperson immediately shifted into pitch mode: “This is Samsung’s latest flagship model.” “It has a 200 MP camera for incredible photos.” “The battery life is amazing—up to two days on a single charge.” “It supports super-fast charging and comes with the latest Snapdragon processor.” The problem? Drita had spent the last month researching the Galaxy S24. - Read reviews - Memorised all the specs - Compared it to other brands - Watched countless unboxing videos In fact, she could have probably *taught* the salesperson a thing or two. She wasn’t there for the specs. She came to see how it felt in her hand and test the camera live. The salesperson’s mistake? They treated Drita like she was at the start of the buying journey instead of recognizing she was near the finish line. So, we left. Because when you don’t feel heard, you don’t spend money. The lesson? Stop pitching the same way to everyone, every time. How? Shift from pitching to asking. Here’s what asking sounds like: Salesperson: “It seems like you already have a phone in mind.” Drita: “Yes, the Galaxy S24.” Salesperson: “You’ve probably done some research already.” Drita: “I have.” Salesperson: “What’s most important to you when choosing a phone?” Drita: “I want to see how the camera performs in low light and make sure it feels comfortable to hold.” Salesperson: “Let me set it up for you so you can test the camera and see how it feels.” The lesson? People don’t buy when you pitch them. They buy when you understand them. PS. She ended up buying a Google Pixel online, avoiding another salesperson altogether.