Kevin Bolger

The Art of the VC Pitch: A Brief Guide to Maximizing Your Chances With Venture Capital Through Giving Better Pitches Pitching to a Venture Capital firm is different from any other kind of pitch. It's not like a sales pitch, a product pitch, or any other kind of presentation. This guide is a road map to the nuts and bolts of maximizing your opportunity when you manage to get in front of VCs

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SaaS founders that cracked $10M ARR have two things in common: 1/ Focus on Onboarding > Marketing  Churn is the obstacle for hitting 8-figures. Experimenting with pricing often and offering solid trials, educational materials, & customer support is key. 2/ Build a Great Team  You can get far with a tiny team, but there’s a threshold. To surpass $10M, you need to find top-tier talent and get out of their way.

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Using Creative Finance to Grow Without Limits One of the secrets behind my 45 revenue streams is simple: creative finance. Whether it’s using seller financing, DSCR loans, or leveraging other people’s assets, I find ways to scale without draining my own capital. This allows me to take on new ventures and expand existing ones without risking the stability of my portfolio. You don’t need piles of cash to make big moves—you need the right mindset, the right strategy, and the willingness to get creative. --- Multiple Industries, Multiple Wins Here’s the thing—diversification isn’t just about safety. It’s about domination. My companies span multiple industries: logistics, real estate, e-commerce, tech, and more. By having a foothold in each, I’ve been able to weather market shifts, capitalize on trends, and always keep my businesses moving forward. For example, my logistics company doesn’t just make money by moving goods. We also own parking lots and storage facilities—two completely separate revenue streams tied to one business. In e-commerce, we don’t just sell products. We have subscription services, white label opportunities, and licensing deals. It’s about taking one business and turning it into a multi-layered income generator. --- Maximizing Every Hour People talk about “working hard,” but the truth is, if you’re making a few hundred bucks an hour, you’re not thinking big enough. Most days, I’m making well over $3,000 to $5,000 per hour, and that’s because I’ve designed my businesses to be efficient, scalable, and profitable across multiple channels. I don’t spend time on low-value tasks because I’ve structured my companies to generate high returns without needing me to micromanage every detail. Automation, delegation, and strategic partnerships are key. You can’t scale to 9 figures if you’re tied to every single decision in your business. --- Building a Legacy Breaking into the nine-figure club isn’t just a goal—it’s an inevitable outcome when you’ve built something with this much momentum. Every one of my 45 revenue streams is strategically aligned to fuel growth, reinvest profits, and compound success. I’m not looking for quick wins or one-hit wonders. --- Final Word - Are You Thinking Big Enough? If you’re reading this and you’re still thinking about running just one business, you’re thinking too small. If you’re settling for one revenue stream, you’re leaving money on the table. You want to scale? You need to diversify. You need to leverage every asset you have. I didn’t build an empire by following the rules—I built it by rewriting them. You’ve got the potential to do the same. #MultipleRevenueStreams #ScalingAnEmpire #CreativeFinance #DiversifyAndDominate #EntrepreneurialMindset #HighValueStrategy #9FigureVision #LeverageForSuccess #BuildingALegacy #ThinkBigActBigger #noexcuses #tylerkania #LegacyBuilding #legacyventure

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⚖ How to leverage small VC funds: (even if they're under $100m) (h/t James Heath) 1. Recognize that 91% of top VC funds are under $250m. 2. Understand that 73% of these are under $100m. 3. Small funds often fit better with your risk/reward profile. 4. Don't dismiss a fund just because it's small. 5. Look at how crowdfunding dynamics are shifting. 6. Analyze how these trends affect the broader market. 7. Focus on companies with strong growth potential. 8. Use qualitative and quantitative metrics to assess investments. - What's the company's growth trajectory? - How strong is their market position? - What are their key performance indicators? - How does media influence their public perception? - What are the regulatory challenges they face? 9. Investigate the impact of successful pitches on funding. 10. Consider the role of community-driven investments. 11. Understand the regulatory landscape for crowdfunding. 12. Address regulatory challenges for sustainable growth. 13. Discuss innovation and economic inclusion. 14. Promote the democratization of finance. 15. Equip yourself with insights to navigate this ecosystem. 16. Stay informed and adapt to new investment trends. You now have the insights to make informed VC allocations. Good luck! ♻️ Repost this if you agree. PS: If you're still on the fence with investment crowdfunding, let me take you by the hand here: [ https://lnkd.in/ejgzhQQa ] 01. Scroll to the top. 02. Click "Ready to invest? GO HERE!"  03. Follow Yvan De Munck to never miss a post. 04. Follow RegCF Rocket on Spotify. 05. Follow RegCF Rocket on Instagram.

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Great post Santosh Sharan 1. If I am reading this correctly, you were in line with what Peter Drucker repeatedly said in classes I was blessed to have taken "Focus on market share and revenue (margins) will follow". 2. I always encourage Startup Clients from Concept through Seed phases: 1. Solid Data Supported Market Analysis (Total Market, SWOT Analysis) 2. Methodical, Low Cost, Essential Features and Fast MVP 3. Traction & Market Share Naturally, I encourage building the business plan immediately and continuously strengthening it. Thanks again for this great launch testimonial!

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How to Pitch a VC: The Essentials When pitching to a VC, it's all about getting to the point quickly and making a strong impression. Here’s what to focus on: 1) The Elevator Pitch: Nail the 30-second quick pitch—be concise and memorable. 2) The Problem & Solution: Clearly define the problem you're solving and why your solution is the best. 3) Market Size: Show the potential for growth and scalability with concrete numbers. 4) Business Model: Demonstrate how you plan to make money and reach profitability. 5) Team: Highlight the superstars on your team who will drive success. PS. check out 🔔 for a winning pitch deck the template created by Silicon Valley legend, Peter Thiel https://lnkd.in/ejp-Bhnu

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Startup decks vs Business plans. It's accepted that a startup needs a deck. Dax Dasilva of Lightspeed Commerce made an important point on 20VC. Writing a business plan - including financial projections - is an important step. It requires discipline. It provides a rigorous framework for thinking deeply about the problem you're trying to solve. Harry Stebbings countered that he doesn't even want to see a deck since it's all dreams. We spent a lot of time and energy on our business plan with the expectation that we would show it to no one ever. The business plan was part of our roadmap for the company. We researched customers - including having 50+ conversations. We wanted to understand them: their background, their interests, their presence on social media. We also wanted to understand how they were evaluated by leadership and how integrated they were with the business of the company they were protecting. We researched pricing both with potential customers and other products in our industry to find out if OpEx or CapEx was a better fit. How did they buy today? How would they like to buy? We did market research to understand the verticals and map the right entry point - we were wrong but that doesn't reduce the value of the research. We looked at competitors in depth to understand what they were seeing that we weren't. Dax is right. This is an invaluable document that should be updated every year - the company is changing, the market is changing, there's more feedback about price and ICP. It's not for sharing with the outside world. It's a map for driving forward. Decks won't get you investment - VCs invest in people. We make decks but we know they don't tell our story. The deck is a calling card. Dax and Harry are both right. https://lnkd.in/e25M82xY

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VCs rate STARTUPS, should the SBA or BBB (Better Business Bureaus do the SAME? Often a complicated and lengthy process for complaints reduces feedback. By Providing a RATING (like RESTAURANTS receive from the health department (ABCD)) that provides a clear metric 📊 on our local SERVICE PROVIDERS who too often can hide 🙈 TRUE results behind SEO (Search engine optimization) or (PPC) pay-per-click that many seniors and homeowners mistake for objective reviews? Whether raising future FUNDING from investors or calculating VALUE, how can consumers better understand and reward great service? How can COMSUMER PROTECTION learn from and mimic VCs IDEA: Dept of Due Diligence ?

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The "lotto effect" is a real problem for startups raising VC. You've struggled for years and suddenly you have $Ms in the bank. The first 6 months is a dangerous time. Here's how to avoid blowing up your team and your company. First, let's acknowledge that landing funding feels f****g great. It's a euphoric mix of validation, relief, and terror. The loss of financial constraints is exhilarating, the world is yours to take. 💪 Damn it, brain. The lotto effect occurs because a windfall gain interferes with our baseline judgements and future expectations. We get excessively optimistic about the future and our ability to engineer it. Risk On. And it's not just founders, it happens to VCs too. They are more aggressive early in their fund cycle than late, and new VCs are more aggressive than salty old vets. Being flush with new cash affects *everyone* because we're all slaves to dopamine. The good news is the lotto effect tends to be short term. Your expectations will reset to with time. So, to improve your chances of success, we want to limit our exposure to excessive risk taking while we are vulnerable. The best approach is to constrain your behavior in advance. Prior to the funding round do the following: - Set clear strategic objectives for growth and product based on your above forecasts. Be clear about order of operations, prioritize. - If you expect to raise again (e.g. series A), model performance criteria for that round now and work backwards. Set realistic metrics. - Create an operating budget with only modest increases in spending for 6-12mo. Plan to ramp spending gradually in line with performance data, not ahead of data. Scale growth ahead of spending. Stick to it. - Create an org. chart and a hiring plan that aligns with the strategic plan. Hire gradually to deliver the plan, not ahead of the plan. - Establish a monthly and quarterly performance review cadence for the executive team. Keep everyone accountable for progress. - Be highly skeptical of wishful thinking, magical hires, or multiple parallel 'strategies'. Focus on delivery and hypothesis validation, not hope. Common failure modes: - Lack of focus. i.e. pushing multiple initiatives in different markets. - Product bloat. Competing with everyone to capture everything. - Over hiring. Adding capacity instead of relieving critical constraints. - Over confidence. Poor executive control, excessive risk taking (short runways), under reliance on customer feedback or performance data. - Premature scaling. Fundraising doesn't fix product market fit. Throwing people at PMF problems usually ends in tears (see Humane). As a founder, you want to use the new capital to de-risk your investment, and then amplify it. Remember, for every dollar you spend you need to create $3-$5 dollars in enterprise value. Raised $5m? You need to create $15M-$25M in value. That's a huge task. Venture dollars are expensive. Good luck!

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The two main reasons I see PLG SaaS Startups reaching a plateau before they hit $10M ARR: 1️⃣ Mathematical limits of the PLG model If you are serving SMBs with a pure Product-Led Growth (PLG) strategy, it is almost impossible to reach Net Revenue Retention of 100%+. Therefore, it becomes increasingly difficult to maintain the same growth rates as you scale. Inbound cannot be scaled indefinitely, and your churn inhibits further growth. Companies that achieve outsize performance are able to successfully switch to a hybrid motion, combining PLG elements with a more traditional enterprise sales model - also called "Product-Led Sales". 2️⃣ Founders fail to build an organization They were able to built a great product and reached product-market fit, but surpassing a certain ARR mark typically requires a shift in focus. From pure product development to building a robust organization. This usually includes expanding the team, establishing processes, introducing strategic planning, cultivating company culture, and often, diluting founder's control and vision for the company. Not every founder is able or interested in making any of those shifts. And I think that's totally fine :-) PS: If you would like to read more on 1️⃣ and 2️⃣, you will find links to relevant saas.wtf articles below.

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Most Pioneer Fund companies send monthly updates (some quarterly), and we read every update across the portfolio of 500+ companies. I actually still personally read every update. Most startups send updates with these sections, and it works well: - High level metrics (revenue, maybe another key metric or two like GMV or MAU, growth since last month, cash in bank, burn rate, runway). Many of the most consistently-growing or fastest-growing companies also include a revenue graph. - Highlights - Lowlights - Investor asks - Maybe a couple investor shoutouts from last month - Some short commentary on what the current priorities are, what's coming next, etc. Some founders like to include a special section or two. A few of my favorites: - Photos or videos of technical progress for hardware companies - One of our founders sends a self rating on a scale of 0-10 for the month, along with detailed explanation. Pretty impressive. - A zoomed out view of how the mission/vision/strategy is specifically evolving - Some have very detailed additional sections that are specific to their business. E.g. manufacturing updates, distribution updates, regulatory updates, etc. Each investor update may only take a few minutes to read, but they are the summary of the hard work of an entire team for an entire month, often fighting uphill or sprinting downhill or exploring the idea maze. We're always grateful reading them.

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Marc Andreessen, cofounder of a16z, on the most common fundraising mistake that founders make: "The single biggest thing entrepreneurs are missing on fundraising and how they run their companies is the relationship between risk and raising cash." - Marc Andreessen The lesson? Understanding risk and its impact on your ability to raise funds is crucial. As entrepreneurs, it's vital to not just chase cash but to build a business model that intelligently manages risks. A clear and impactful message, encouraging entrepreneurs to reevaluate how they approach the crucial stages of building and funding their companies. By aligning risk management with your fundraising strategy, you open the door to more sustainable growth and success. PS. Check out 🔔 for a winning pitch deck template created by Silicon Valley legend, Peter Thiel! https://lnkd.in/ejp-Bhnu

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Here are 15 IPOs w/ <$500M in revenue. They did more than fine. 9x+ since IPO. The narrative that "only massive companies doing >$700M in revenue can go public" is false. smaller cos can 100% go public w/ good growth + efficiency (rule of 40).

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12 ideas from Don Valentine (founder of Sequoia) 1. There are two things in business that matter, and you can learn this in two minutes- you don’t have to go to business school for two years: high gross margins and cash flow. The other financial metrics you can forget. 2. The trouble with the first time entrepreneur is that he doesn’t know what he doesn’t know. After a failure, he does know what he doesn’t know and can beat the hell out of people who still have to learn. 3. The world of technology thrives best when individuals are left alone to be different, creative, and disobedient. 4. The art of storytelling is critically important. Most of the entrepreneurs who come talk to us can't tell a story. Learning to tell a story is incredibly important because that's how the money works. The money flows as a function of the stories. 5. We don't spend a lot of time wondering where people went to school. We are interested in their idea about the market they are after. The magnitude of the problem they are solving. 6. We don't wait for you to knock on our door. We knock on your door. 7. The right people to invest in are technologists. People who have a dream to solve a problem. Most were not interested in becoming wealthy. That was an accident. They were interested in solving technology problems and creating new products. 8. One of my jobs as a board member has been to counsel management to avoid distraction and to execute with constructive paranoia. 9. Think about a company like Eastman Kodak – it was the leader in its market, and now it’s gone. How can a $100 billion company go out of business? The answer is, easily and quickly. 10.We don't choose people. We choose markets. 11.We have gone into business with some people who had no business credentials. We taught them that you only had to do a few things well. 12.All companies that go out of business do so for the same reason – they run out of money. #DonValentine #business #companies #success #grow

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Fundraising for your SaaS startup? We all know about the pitch deck— The fundraising process revolves around it. But let me introduce to you something more powerful: The data deck. It’s the most effective tool I’ve used in every fundraising round… …from a $16M Series A to a $120M Series D. Here's what investors *actually* care about: - Revenue - Acquisition - Engagement - Retention - Financials But having the numbers lined up is just the beginning. You must also… - Tell your story through data - Anticipate investor questions - Frame metrics against successful peers Don't leave your fundraising to chance. I've broken down the exact metrics you need below— Use it to build your data deck and nail your next round ↓

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Y Combinator's latest batch is working on interesting growth tech (sales/marketing). Some you should know: 1. Topo.io (YC W24) - Train your AI agent by answering a few questions. It then identifies the right leads for you, crafts a personalized outreach, and books meetings for you. Co-Founder Dan Elkaïm previously led Aircall's strategic sales from 10 to $120M ARR. 2. Ecliptor (YC W24) - Selling to developers is unique; your touchpoints include Posthog, GitHub, LinkedIn, Slack, Discord, etc and website/documentation visits. Co-Founders Andre Fu and Nanki Grewal previously built and sold a devtool after working on ML at Twitch. They now use AI to help devtools find their product champions and close enterprise customers. 3. PartnerHQ - A marketplace for B2Bs to buy warm intros. Founders: Kat Wang was employee #4 at UVS Games helping them take from $500k to $20M in 1 year. She was previously at Affinity (CRM used by 40% of VCs). Stan L. was the founding engineer at Notable Health ($120M raised) and helped grow revenue from 0 to $60M ARR. He wrote software that manages healthcare data for 60% of the US population. 4. Resonance - PLGs rely on in-product messaging to drive feature adoption, retain users, and drive in-product upsells. Founder Jonathan Ou was previously at Dropbox, DoorDash, and Microsoft. He helped build a platform similar to Resonance at Dropbox that generated $100M ARR. . . Congratulations to these founders!! 🚀 Already signed up to a few trials/demos. I found this batch to have super solid teams, tight pitches, and excellent execution. Definitely taking notes and will keep an eye on several products from W24.

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How to buy a business and 10x its value with a DM and AI in 2024: 1. Use Sourcescrub to identify promising businesses not yet on the market. 2. Leverage IndieHackers' "Milestones" feature to find founders ready to exit. 3. Use Octoparse to scrape Acquire .com listings, then leverage GPT-4 to identify and DM similar unlisted startups (or just buy on Acquire). 4. Deploy GPT-4 to craft hyper-personalized cold DMs to founders on Twitter and LinkedIn. 5. Implement Phantombuster to automate multi-channel outreach to potential sellers. 6. Use Clearbit Reveal to identify/reach out to founders on your website. 7. Leverage Apollo IO for targeted lead generation and automated email sequences. 8. Deploy Mailshake for A/B testing cold email campaigns to founders. 9. Use Dux-Soup for automated LinkedIn prospecting and relationship building. 10. Implement Pipedrive's AI sales coach for optimizing your acquisition funnel. 11. Use Gong IO to analyze and improve your pitch calls with potential sellers. 12. Deploy Hotjar on target sites to identify quick UX wins post-acquisition. 13. Use ClickUp's AI to create and manage your entire acquisition workflow. 14. Implement Clearscope for immediate content optimization of acquired sites. 15. Use RankScience for automated A/B testing of SEO changes on acquired sites. 16. Deploy Jasper ai for rapid production of SEO-optimized content at scale. 17. Use Crayo AI for faceless video creation and build many pages driving free traffic. 18. Use Customers AI to drive anonymous visitor traffic into your free Skool, WhatsApp, or FB Group community. 19. Leverage Surfer SEO for identifying quick content optimization opportunities. 20. Use Frase IO for AI-powered content briefs to quickly fill topical gaps. 21. Implement Oribi for immediate conversion funnel analysis post-acquisition. 22. Use Mutiny for rapid personalization and CRO of acquired websites. 23. Deploy Ahrefs' Content Explorer to find high-performing content ideas in your niche. 24. Use OpenAI's GPT-4 to generate dozens of ad variants for rapid PPC testing. 25. Use Mention's AI to monitor brand sentiment & identify businesses with potential. 26. Deploy Octup . us for AI-driven financial forensics to uncover hidden value in targets. 27. Leverage Unito . io to seamlessly integrate tools post-acquisition, reducing friction. 28. Implement Viable for AI-powered analysis of customer feedback to identify quick wins. 29. Use Synthesia to create AI spokespersons for acquired brands, cutting video costs. 30. Deploy Adext AI for autonomous optimization of ad spend across platforms. 31. Use Anyword's AI to dynamically personalize website copy based on visitor behavior. 32. Implement Signality for AI-driven competitive intelligence to inform negotiations. 33. Use Featurebase to crowdsource product ideas 34. Hire DesignScientist.com for a rebrand By the way, I put together a list of 30+ free biz ideas for you to take https://lnkd.in/eKicBBqe (most require no VCs)

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Dalton Caldwell is Managing Director and Group Partner at Y Combinator. During his time at YC, he’s worked with over 1,000 startups, advised more than 35 YC unicorns—including DoorDash, Amplitude, Webflow, and Retool—across 21 different YC batches, and racked up more than 6,500 office hours with founders. In our conversation, we explore: 🔸 How to not die 🔸 The most common reason startups fail 🔸 Characteristics of a good pivot 🔸 “Tar pit ideas” (i.e. common bad startup ideas) 🔸 Why investors say no to startups 🔸 The importance of market size 🔸 Why founders over-delegate 🔸 Tips for talking to customers 🔸 20 ideas Dalton is looking to fund 🔸 Much more 🔥 Key takeaways below. Listen now 👇 YouTube: https://lnkd.in/ewZ5w78x Spotify: https://lnkd.in/eeTCeSxm Apple: https://lnkd.in/eVTQgeFf Key takeaways: 1. The defining trait of successful founders isn’t a specific personality type but rather a profound self-belief. They possess an unwavering conviction in their startup’s potential, even in the face of daunting obstacles. Refusing to accept failure, they persuade others of their inevitable success. 2. Beware of “tar pit ideas”: ideas that receive initial positive feedback but may lead to long-term challenges. These ideas often seem appealing and solve what appears to be an unsolved problem, attracting many people to pursue them. However, despite the positive feedback and validation, they can become difficult to pivot away from once their limitations become apparent. Understanding the distinction between a genuinely innovative startup idea and one that merely garners initial enthusiasm can save founders time, resources, and energy in the long run, steering them toward more promising ventures. 3. A successful pivot often entails focusing on familiar problems and refining previous solutions. Companies like Brex and Segment thrived after significant pivots that drew on founders’ prior experiences and insights gained from initial concepts. 4. If your venture struggles and innovative strategies are exhausted, consider pivoting. But if there are still untapped ideas, persevere and try them first. 5. If an investor likes aspects of a startup, they may still say no because they are waiting for opportunities that meet a higher bar. Dalton says to put yourself in the shoes of investors and consider what decisions they would make if they were in that position. This perspective can help founders understand that rejections aren’t necessarily a reflection of lack of belief in their idea but rather a result of investors seeking the most promising opportunities given their constraints.

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