Mastering the Art of Pitching

I’ve been cold calling for 9 years. Here’s everything I know about it: (this is a longer post so bear with me) 𝟭. 𝗧𝗵𝗲 𝗳𝗶𝗿𝘀𝘁 𝟭𝟬 𝘀𝗲𝗰𝗼𝗻𝗱𝘀 𝗺𝗮𝘁𝘁𝗲𝗿 𝗺𝗼𝗿𝗲 𝘁𝗵𝗮𝗻 𝗮𝗻𝘆𝘁𝗵𝗶𝗻𝗴: People don’t hang up because it’s a cold call. They hang up because you sound unsure, scripted, or boring. - Be calm. - Be confident. - Be clear. 𝟮. 𝗦𝗸𝗶𝗽 𝘁𝗵𝗲 𝘀𝗺𝗮𝗹𝗹 𝘁𝗮𝗹𝗸: Don’t ask “𝘏𝘰𝘸’𝘴 𝘺𝘰𝘶𝘳 𝘥𝘢𝘺 𝘨𝘰𝘪𝘯𝘨?” Don’t ask “𝘐𝘴 𝘯𝘰𝘸 𝘢 𝘣𝘢𝘥 𝘵𝘪𝘮𝘦?” Just try: “𝘏𝘦𝘺 (𝘯𝘢𝘮𝘦), 𝘐 𝘬𝘯𝘰𝘸 𝘺𝘰𝘶 𝘸𝘦𝘳𝘦𝘯’𝘵 𝘦𝘹𝘱𝘦𝘤𝘵𝘪𝘯𝘨 𝘵𝘩𝘪𝘴, 𝘐’𝘭𝘭 𝘬𝘦𝘦𝘱 𝘪𝘵 𝘴𝘶𝘱𝘦𝘳 𝘣𝘳𝘪𝘦𝘧.” That opener alone will double your talk time. 𝟯. 𝗣𝗶𝘁𝗰𝗵 𝘁𝗵𝗲 𝗽𝗿𝗼𝗯𝗹𝗲𝗺, 𝗻𝗼𝘁 𝘁𝗵𝗲 𝗽𝗿𝗼𝗱𝘂𝗰𝘁: No one cares that you’re the “𝘯𝘰.1 𝘱𝘭𝘢𝘵𝘧𝘰𝘳𝘮 𝘧𝘰𝘳 𝘟.” Tell them what pain you solve, fast. 𝟰. 𝗢𝗯𝗷𝗲𝗰𝘁𝗶𝗼𝗻𝘀 𝗮𝗿𝗲𝗻’𝘁 𝗿𝗲𝗷𝗲𝗰𝘁𝗶𝗼𝗻𝘀: “I’m not interested” just means they don’t understand you yet. Use the FFF method: Feel - Felt - Found. “𝘐 𝘨𝘦𝘵 𝘵𝘩𝘢𝘵. 𝘖𝘵𝘩𝘦𝘳𝘴 𝘧𝘦𝘭𝘵 𝘵𝘩𝘦 𝘴𝘢𝘮𝘦… 𝘣𝘶𝘵 𝘸𝘩𝘢𝘵 𝘵𝘩𝘦𝘺 𝘧𝘰𝘶𝘯𝘥 𝘸𝘢𝘴 (𝘣𝘦𝘯𝘦𝘧𝘪𝘵).” 𝟱. 𝗧𝗵𝗲 𝗴𝗼𝗮𝗹 𝗶𝘀𝗻’𝘁 𝘁𝗼 𝘀𝗲𝗹𝗹, 𝗶𝘁’𝘀 𝘁𝗼 𝘀𝘁𝗮𝗿𝘁 𝗮 𝗰𝗼𝗻𝘃𝗲𝗿𝘀𝗮𝘁𝗶𝗼𝗻: If they’re talking, you’re winning. If they’re curious, you’re in. If you book the meeting, that’s the win. 𝟲. 𝗩𝗼𝗹𝘂𝗺𝗲 𝗶𝘀 𝗶𝗺𝗽𝗼𝗿𝘁𝗮𝗻𝘁: You could have the best pitch in the world… But if you don’t make the dials, you won’t get the meetings. Consistency > perfection. 𝟳. 𝗬𝗼𝘂 𝗰𝗮𝗻'𝘁 𝗯𝗼𝗼𝗸 𝗺𝗲𝗲𝘁𝗶𝗻𝗴𝘀 𝘄𝗶𝘁𝗵 𝗲𝘃𝗲𝗿𝘆𝗼𝗻𝗲: Don’t waste time trying to convince people who don’t have the problem you solve. Laser focus on your ICP, the ones who feel the pain. 𝟴. 𝗧𝗿𝗮𝗰𝗸 𝘆𝗼𝘂𝗿 𝗲𝗻𝗲𝗿𝗴𝘆: Your tone > your script. People say yes to people who sound like they believe in what they’re saying. 𝟵. 𝗙𝗼𝗹𝗹𝗼𝘄-𝘂𝗽 𝗹𝗶𝗸𝗲 𝘆𝗼𝘂𝗿 𝗹𝗶𝗳𝗲 𝗱𝗲𝗽𝗲𝗻𝗱𝘀 𝗼𝗻 𝗶𝘁: Most meetings I book happen after the call. Send a short LinkedIn DM or a value-driven email right after. 𝟭𝟬. 𝗧𝗵𝗲 𝗯𝗲𝘀𝘁 𝗿𝗲𝗽𝘀 𝗱𝗼𝗻’𝘁 𝘄𝗶𝗻𝗴 𝗶𝘁: They have a framework. They prep. They reflect after each call. And they improve daily. Cold calling still works if you do it right. Now let's book some meetings!!!! P.S. I've created a free cold calling cheat sheet where I share all of my do's & don'ts. You can access it for free here: https://lnkd.in/g9BrrDA6

There's a simple test for any pitch: if an investor can't hear your story once and retell it to their partners, you don't have a story. Instead, you have a feature list. And feature lists don't survive the partner meeting. A founder walks in with a deck that's technically correct. The logic is airtight. The analysis is thorough. But five minutes in, you can feel the room getting bored. Economists have a name for this: the "curse of knowledge." Once you know something deeply, you can't remember what it felt like not to know it. So you try to "catch them up." You give background. You show the architecture. You pre-answer objections. But every pitch runs on a clock. You have 30 seconds to earn the next 30. And most founders waste those seconds because they treat communication like garnish instead of what it really is: the thing that determines whether their idea lives or dies. There's a metaphor in consumer advertising: "Throw someone one egg and they'll probably catch it. Throw them five and they drop them all." Most founder pitches are five eggs. Here's how to throw one egg: 1. Start with the shift, not the solution Name what changed in the world. Investors decide whether to care first. Only then do they decide whether the thing is good. 2. Show winners and losers Humans feel losses more strongly than gains. Make the cost of missing this wave vivid. 3. Paint the promised land before you explain the product They need to want the destination before they'll care about the vehicle. 4. Present obstacles, then your solution as the thing that makes the hard thing achievable If the promised land were easy, everyone would already be there. Make the struggle explicit. Paul Graham put it well: putting ideas into words is a "severe test." You discover you didn't know the idea as well as you thought. That's why founders hide behind spreadsheets. Numbers feel safe. Narratives feel exposed. But you can have the strongest analysis in the room and still lose to the founder with the simpler, more legible story. Your job is to design for the human on the other side of the table.

Struggling to open up sales calls? These 4 opening tips are making my cold calls much warmer 🌤️ 1. Email or LinkedIn them first, then acknowledge this at the start of the call 📧 A cold call is never really cold if you’ve made an attempt to communicate async first People are a lot more receptive to giving to time when you’ve done this e.g. “Sent you an email earlier and thought I’d pick up the phone to see if it was worth a chat; did you get that one?” If they have, ask them what they thought! If they haven’t, give them a summary to save them time h/t Jake McGaw for suggesting this one 2. Ask them how they’re going and assuming they ask back, give a genuine response about something that happened in your day 😊 Simple way to build a genuine human connection over the phone rather than sounding like a call centre employee robotically reading a script Talk about your morning exercise, a recent meal, something funny that happened in the office e.g. “Yeah not too bad! Skipped breakfast this morning and was instantly regretting it by 11, so just gulped down a protein smoothie” h/t Samuel Westley, an Earlywork grad who is GREAT at this 3. Lead with personalised context to build trust that your call is well-researched and relevant to them 📝 e.g. “Hey X, saw you recently listed your first Junior Sales Consultant role, it’s Dan Brockwell from Earlywork” (can also use this info after Steps 1 and/or 2) 4. Use lower modality language in your ability to help them and get permission to ask questions to find out if you can 🙏 It comes off a lot less pushy and builds more trust that you don’t want to waste their time + genuinely want to understand their situation e.g. Thought your role may be a fit for some of our students, but okay if I ask a question or two to better understand whether it would make sense?” — Would love to hear any unconventional call openings that you’ve found are working well for you / your sales team :)

Stop practicing on your prospects. You're throwing away opportunities. Don't get me wrong, the best way to learn is by doing. But you shouldn't try out a new talk track for the first time in a live situation. You would never apply this logic in any sport. In most sports, you practice far more than you play. By a factor of 5 or even 10:1. Here's how you can leverage ChatGPT to practice cold calling: ✅ Prompt "You are a [persona] who works at a company like [typical target account]. You're busy, hard to get a hold of, and you're not going to like that I'm cold calling you. I've attached my cold call talk track, along with how I should be handling objections. Please follow the Outbound Squad framework. I've also uploaded a few transcripts from recent cold calls with this persona. Use that as a guideline for how these calls usually go. Here's my company [website URL] so you have a better idea of what I do. I want to role-play a cold call with you. Here's exactly what you should be critiquing: 1. Intro I will be using a permission-based intro. Listen to see if I stumble over my words, don't sound confident, or hesitate. If I do any of those things, give me an objection. Or hang up. I will then use a Reverse Pitch. The idea here is NOT to pitch my product. But to pitch the problems we hear from your peers. Again, if you hear me start to pitch the product—give me an objection or hang up. 2. Hook During this call, we should get to a problem you might have that our solution could solve. I should be engaging you with great questions to find problems. Feel free to throw out more objections as well. If I don't do a great job of handling those objections, hang up. 3. Close Lastly, I should be making an explicit ask for the meeting. When I set the meeting, you should be listening for a triple confirmation. I should confirm the day/time with you and ask you to accept the calendar invite on the call. I should be confirming the agenda with you. Lastly, I should let you know the confirmation process. After I complete the call, I would like feedback on two things I did well and two areas for improvement. Got it? Let me know and I'll speak with via voice." ✅ Practice Send that promp. Then start talking back and forth with ChatGPT. This works best on the premium version. I like to do this for about 10 min before a cold calling block. Or anytime I'm trying to work out new messaging. ~~~ Leslie Venetz joined the Outbound Squad podcast to talk about practice and much more. Check out the full interview here: https://lnkd.in/edH7_vV8 How are you leveraging AI to practice your cold calls?

If you’re pitching on a cold call, you’re losing. Why? Pitching makes you the persuader. Which makes them the defender. The moment a prospect feels even a hint of “Here comes the spiel,” their brain hits the brakes. The shields go up. The Zone of Resistance kicks in. Asking does the opposite. Asking lowers resistance. Asking makes people think instead of retreat. That’s where poking the bear comes in. Shining a light on a potential problem then inviting the prospect to reflect on it. Here’s an example: “Not sure about your team, but SDRs usually have two or three conversations per 50 dials. Even with direct numbers most people don’t answer. How do make sure reps aren’t calling prospects who never pick up?” Then shut the front door. Why this works: You’re giving their brain a small puzzle to solve. You’re creating that hmm… hmm, good question moment. You’ve piqued curiosity. You’re having a dialogue rather than giving a monologue. Prospects have the answers. Sellers have the questions.

The worst pitch decks don’t fail because of bad ideas. They fail because of poor storytelling. Healthtech founders often think investors will “get it” if they just see their tech. Spoiler - they won’t. If your STORY isn’t clear, your pitch won’t land. Here’s how you can simplify it: 1. Start with the why, not the what Don’t lead with product features. Start with a real pain point investors can feel, not just understand. 2. Ditch the jargon If they can’t repeat what you do in one line, you’ve lost them. Say: “We help doctors detect cancer 3x faster” Not: “AI-powered clinical decision support system.” 3. Let numbers do the talking Don't claim your product is impactful - prove it. Instead of saying "We're improving patient outcomes," say "Reduced patient readmissions by 25% in 3 months." 4. Make your business model obvious Investors want returns. Who pays? How do you scale? Show the path to profit early - don’t hide it in slide 15. 5. Close with a vision, not just an ask Skip the boring close. Say: “We’re building a future where every patient gets the right treatment - starting with 500 hospitals in 2 years.” The best pitch decks aren’t just data dumps. They’re stories. And the founders who master storytelling don’t just raise money. They build category-defining companies. If an investor only remembers one thing from your pitch, what would it be? #startups #funding #founders #healthtech

Most founders get pitch decks completely wrong. They spend weeks perfecting slide designs. They cram 20+ slides with unnecessary details. They forget the fundamentals. I have reviewed, revamped, and built from scratch 1000+ pitch decks for startups at all stages, and here's what actually matters... Your pitch deck has ONE job. Answer two simple questions: → Will this make investors money? → Can your team actually deliver? That's it. Everything else is noise. The 6 slides that matter matter most: 1️⃣ Problem: Is this a real pain that people desperately need solved? Not a nice-to-have. A must-have. 2️⃣ Solution: How does your product solve this pain better than anything else? Be specific. 3️⃣ Market Size: Is this big enough for a billion-dollar outcome? If not, most VCs won't care. 4️⃣ Traction: What proof do you have that customers want this? Revenue beats promises every time. 5️⃣ Competition: If others exist, why will you win? If nobody's solving it, why now? 6️⃣ Team: Why are you the right people to build this? Results matter more than fancy resumes. Here's what most founders miss... They think about stages wrong. Pre-seed investors bet on teams and big problems. Seed investors want early validation. Series A investors need proven unit economics. Know your stage. Pitch accordingly. The brutal truth? Beautiful slide design won't save a weak business model. Fancy animations won't hide lack of traction. Perfect formatting won't fix team capability issues. Focus on substance over style. 📍 Pro tip: The team slide gets the most attention. Know why? Investors pause to Google every team member. Your credentials matter. But your ability to execute matters more. Bottom line... Stop overthinking your deck. Start proving your market exists. Show why customers will pay for your solution. Demonstrate your team can scale. The rest is just packaging. What's the biggest mistake you see in pitch decks? And if you're preparing to raise, what stage are you at? Let me know in the comments. --- I'm Nidhi Kaushal, founder of Team Flexbox. We help startups with strategic fundraising support. If you're preparing to raise capital and want a deck that actually converts, let's chat. Book a 1:1 call through the link in my bio or send me a DM. Let's turn your vision into a fundable reality.

I’ve helped review countless pitch decks and have distilled some of the most impactful insights for founders looking to make a lasting impression on investors: - Start by building trust: Use facts to establish trust before jumping into future projections. Most decks I see start with a graph projecting future growth but it’s often dismissed by investors who are by nature, skeptical. Instead, focus the first 60-80% of your deck on factual data — your historical results and achievements. This will allow investors to trust in your story and understand your company’s track record before introducing future potential. - Keep your story clear and simple: Your pitch is essentially a story and it needs to be clear. Make sure investors understand who your customer is, the problem you’re solving, and how you’re uniquely solving it. Founders are often so deeply involved in their business that they tend to dive into the details without laying out the basics. - Use data: After each major point in your story, include a data slide to reinforce it. For instance, if your story is about helping clients succeed, show actual sales growth from customers using your platform. Real, historical data builds trust far more than speculative projections. - Market size: Investors want to know the size of the opportunity. But avoid saying statements like: “The market is $1 trillion, and we just need 1% of it.” The size of the overall market does need to be big enough to support an investment type company — but it’s often better to use a bottom-up approach to explain your potential. - The team: Your team is critical so instead of adding a team slide at the end with some LinkedIn profiles, highlight why you’re uniquely positioned for this business. Even if you don’t have high-profile credentials, you should still highlight your deep passion and relevant experience. - Customer focus: Be clear on who your customer is and what specific problem you’re solving. What other elements can’t be left out of a strong pitch deck? Any other approaches you’ve seen work well?

Everybody is a startup mentor these days. On LinkedIn, advice is abundant. It’s also uneven and sometimes, it’s dangerously wrong. Taking liquidity early in the funding process sounds appealing. Reduce personal risk. Take money off the table. Reward yourself early. But for investors, early liquidity signals the opposite of what they want to see. It signals lack of conviction, lack of commitment, lack of endurance, misaligned incentives, and short-term thinking. Early liquidity in Seed, Series A, or Series B rounds raises immediate concerns. Investors expect founders to be fully aligned with long-term value creation. Later-stage liquidity can make sense. Early-stage liquidity usually does not. This is why not all startup advice is good advice. And more importantly, bad advice often shows up before a founder is truly investor ready. That’s where most mistakes begin. Founders Try to Raise Before They’re Ready - Behind premature fundraising is usually one fear: If I don’t raise money soon, I’ll fall behind. That fear drives founders to pitch before validation exists, overstate traction, copy VC backed narratives that do not fit, give up equity without leverage, and optimize for valuation instead of fundamentals. This is how founders end up chasing funding instead of building fundability. Fundability is earned, not assumed. If you’re wondering whether your startup is truly investor-ready, start by reviewing the full framework here: How to Tell If Your Startup Is Investor-Ready What Investor-Ready Actually Means - Being investor ready is not about passion, vision, a polished pitch deck, a big market slide, or a compelling story. Investors fund evidence, not enthusiasm. Signals of real fundability include clear customer validation, proof of willingness to pay, early revenue or usage traction, credible market segmentation, repeatable customer acquisition, and a capital efficient path to scale. If these signals aren’t there yet, the issue isn’t your idea. It’s simply timing. Why Bad Mentors Push Premature Fundraising - Poor startup advice often follows a predictable pattern: optimizing for fundraising instead of customers, encouraging valuation before validation, promoting speed over discipline, confusing visibility with traction, and rewarding optics over fundamentals. This leads to overfunding, bloated valuations, forced growth, loss of control, down rounds, and shutdown risk. This is exactly what the Bootstrap First, Raise Money Later philosophy is designed to avoid. Instead of asking if you can raise money right now ask: - What evidence is missing? - What milestones would investors expect? - What can I build without dilution - What traction reduces risk? - What strengthens leverage? This shift changes everything. You stop chasing capital. You start building fundability. Come talk to me at a free mentoring roundtable and ask questions of the 1Mby1M AI Mentor: https://lnkd.in/gB69hhqK 

Stop overthinking the opener. What comes next matters more Everyone obsesses over cold call openers ✅ “Should I ask for permission?” ✅ “Do I use a pattern interrupt?” ✅ “What’s the best first line to say?” But here’s the real truth the opener isn’t what books the meeting It just keeps the call alive The real problem? What happens AFTER they say "sure what’s this about?" This is where most reps lose the prospect ❌ They jump straight into a pitch before confirming interest ❌ They assume a problem exists instead of letting the prospect voice it ❌ They talk too much, listen too little I’ve learned that the best approach no matter who you call is 👉  𝘚𝘦𝘦𝘬 𝘧𝘪𝘳𝘴𝘵 𝘵𝘰 𝘶𝘯𝘥𝘦𝘳𝘴𝘵𝘢𝘯𝘥 𝘵𝘩𝘦𝘯 𝘵𝘰 𝘣𝘦 𝘶𝘯𝘥𝘦𝘳𝘴𝘵𝘰𝘰𝘥 How this works for different industries 👉 If you’re calling a 𝗩𝗣 𝗼𝗳 𝗠𝗮𝗿𝗸𝗲𝘁𝗶𝗻𝗴 ❌ “We help brands improve lead conversion rates. Would you be open to learning more?” ✅ “Hey I know every marketer I talk to is dealing with lead quality vs. quantity how’s that looking for you right now?” 👉 If you’re calling a 𝗙𝗮𝗰𝗶𝗹𝗶𝘁𝗶𝗲𝘀 𝗺𝗮𝗻𝗮𝗴𝗲𝗿 ❌ “We provide building maintenance software do you have time to chat?” ✅ “Curious how are you currently managing maintenance requests? Any recurring headaches that slow things down?” 👉 If you’re calling an 𝗜𝗧 𝗗𝗶𝗿𝗲𝗰𝘁𝗼𝗿 ❌ “We help companies improve cybersecurity. Is that a priority for you?” ✅ “Saw your team is growing how are you handling security for new hires working remote?” See the pattern? 📌 Make it about their world. Not yours 📌 Ask a question that makes them think. Not tune out 📌 Hold back your pitch. Earn the right to present your solution Then when they tell you a challenge that’s your in 👊 “That’s exactly why I was calling Tom. A lot of teams are struggling with [pain they mentioned] and we help with that by [tailored value prop]” Now you’re not pitching You’re having a real conversation 𝗦𝗗𝗥𝘀 & 𝗔𝗘𝘀: What’s your go to discovery question for cold calls? Drop it below 👇