Feel the Boot delivers advice and experience to entrepreneurs, helping them create and grow successful businesses. We help founders go from overwhelmed entrepreneur to successful CEO.
Are you outsourcing your thinking to ChatGPT? That's a fast track to sabotaging your startup. In this episode, I share two real conversations I had with founders who said they got their market size numbers from ChatGPT. That is a red flag for any investor. The problem is not that they used AI. The problem is that they didn't understand what the answer meant or where it came from. I walk through the right and wrong ways to use tools like ChatGPT in your startup. Whether you're researching your target market, writing content, or creating your financial projections, you need to know what is solid and what is just noise. You will learn:· When using AI makes sense and when it is a trap· How to ask for citations so you can verify the data· Why AI-generated financials almost always fall apart· What to do instead so you can sound sharp and raise with confidence This isn't about avoiding AI. It is about using it well so you can think clearly, move faster, and make better decisions.
Most founders don't fail because of a bad idea.They fail because fear, doubt, and hesitation stop them before they ever really start. In this episode of Feel the Boot, I sit down with internationally recognized mindset coach David Neagle to talk about what keeps talented people stuck, and how to break free. We explore:Why so many founders never launchThe mindset shift that drives real changeHow to push through fear and uncertaintyThe discipline behind every successful entrepreneurWhy authenticity beats confidence when raising capital or building a team David also shares his powerful personal story, from working a warehouse job to tripling his income in 30 days, and building a multi-million dollar coaching business. If you've been struggling with self-doubt, imposter syndrome, or fear of failure, this conversation will hit home.
Unlocking Startup Growth: Fundraising Strategies and Resilience Tips with Paulo Andrez What separates the startups that raise capital and scale… from those that stall out? In this episode of Feel the Boot, I sit down with Paulo Andrez—angel investor, serial founder, and startup turnaround specialist—to talk about the real challenges early-stage founders face. We dig into:• Why most founders raise capital too early• What investors like Paulo actually look for in a startup• How to recover from failure and pivot the right way• Why founder resilience is more important than brilliance• The biggest reasons startups fail—and how to avoid them If you're working on a startup and planning to fundraise (or already trying), this episode is a must-listen.
Pre-Sell Before You Build: Avoid Costly Startup Mistakes — with David Hirschfeld Most startups fail because they build something no one wants.In this episode of Feel the Boot, I talk with David Hirschfeld, founder of Tekyz and creator of the Launch First method, about how to flip the script and pre-sell your product before you build it. We explore how high-fidelity mockups, early customer conversations, and focused problem validation can help founders avoid wasting time, money, and effort on products that miss the mark. If you're an early-stage founder, this episode is packed with practical advice to help you test, sell, and refine your idea before writing a single line of code.
Avoid These Startup Finance Mistakes — Insights from a Fractional CFO Most founders ignore finance until it becomes a problem—don't be that founder. In this episode of Feel the Boot, I sit down with Josh Aharonoff, a fractional CFO who works with fast-growing startups to get their financials investor-ready. We talk about common finance mistakes, when to hire help, and what investors expect from your financials—especially when raising capital. If you're pre-seed, pre-revenue, or thinking about raising capital, this conversation will help you avoid costly misstepsand get your financial house in order. Read this as a blog: https://ftb.bz/118BWatch the video: https://ftb.bz/118VTake the quiz to see if your ready for funding: https://ftb.bz/fundable
What's stopping you from starting your dream business?For most people, it's fear.Fear of failure, financial loss, looking foolish—or even fear of success.In this episode, we break down the most common fears entrepreneurs face and share actionable strategies to overcome them. Learn how to:✅ Do the research that calms fear of the unknown.✅ Test your idea with quick, low-cost experiments.✅ Build financial and emotional safety nets.✅ Surround yourself with mentors, advisors, and co-founders.✅ Start small and “act as if” you're already a founder. Your entrepreneurial journey doesn't have to be terrifying. Take the first step today—because hope isn't a strategy, but action is.
Why Startup Plans Fail (and Why That's Okay) Welcome to Feel the Boot, the science of startups! In this episode, host I share three insightful sayings about planning and their relevance to startups. Using quotes from Dwight D. Eisenhower, Helmuth von Moltke, and Mike Tyson, I discuss the importance of planning and adaptability when facing unexpected challenges.Learn how to navigate the twists and turns of launching a business and how to pivot efficiently when your plans don't survive first contact.Join the discussion and share your experiences in the comments.Don't forget to like, subscribe, and ring the bell for more valuable content! Get help with your startup https://ftb.bz/boostSubscribe to Boot Prints https://ftb.bz/joinRead the blog https://ftb.bz/115BWatch the Video https://ftb.bz/115V
Building Products Right: Essential Advice for Early-Stage Founders by Chad Perry
In this episode of Feel the Boot, I sit down with leadership expert Emily Hawkins to tackle one of the biggest challenges founders face: effective team management.
In this episode of 'Feel the Boot,' host Lance Cottrell delves into the strategic importance of targeting a niche market for startup success. He guides early-stage founders through the crucial process of focusing on specific customer segments that resonate with their products, illustrating how this can significantly improve customer acquisition and product development. Lance shares practical strategies for selecting a target niche, such as engaging early adopters, leveraging small communities, and identifying underserved markets. This approach not only helps in establishing a strong market presence but also lays the foundation for scaling into broader markets. Tune in to gain invaluable insights into effectively narrowing your focus for better startup execution. Blog https://ftb.bz/112BYouTube https://ftb.bz/112VBootPrints https://ftb.bz/join“Are you fundable?” tool https://ftb.bz/fundable
The freemium business model is popular, but is it right for your startup? In this video, I break down how freemium works, common mistakes founders make, and why it often leads to revenue problems. We'll also explore an alternative approach—the reverse freemium model—that could be a better fit for your business. Ideal for early-stage founders, this video provides valuable insights and practical advice on setting up a successful freemium model, complete with real-world examples and suggestions for effective customer engagement. Blog https://ftb.bz/111BVideo https://ftb.bz/111VSubscribe https://ftb.bz/joinAdvising https://ftb.bz/advising
How to Pivot Your Startup Before You Launch
In this episode of Feel the Boot, host Lance Cottrell delves into the concept of 'secret sauce' for startups. Learn why identifying and protecting your unique differentiator is crucial for attracting investors and maintaining a competitive edge. Cottrell shares insights on developing a valuable and defensible secret sauce, using trade secrets and patents, and the importance of articulating it effectively in your pitch deck. This video is a must-watch for early-stage founders seeking to innovate and secure their business's future. Blog https://ftb.bz/109BVideo https://ftb.bz/109VNewsletter https://ftb.bz/joinAdvising https://ftb.bz/advising
In this episode of 'Feel the Boot,' I address a common frustration among startup founders: investors who show strong interest but delay their commitment. I explain the reasons behind this behavior, such as risk minimization and strategic leverage, and provides actionable techniques for founders to expedite investor commitments. Key strategies discussed include structuring funding rounds in tranches, leveraging social proof, and utilizing time-critical events to encourage quicker investments. Blog https://ftb.bz/108BYouTube https://ftb.bz/108VFundraising playlist https://ftb.bz/fundraising-playlistSubscribe to BootPrints https://ftb.bz/join
Startup Failure Analysis
In this episode of 'Feel the Boot,' Lance Cottrell shares essential advice on crafting an effective elevator pitch to capture the interest of potential investors or partners quickly, stressing the importance of brevity, clarity, and engaging storytelling. He emphasizes that the goal of an elevator pitch is to spark interest for further conversation, not immediate commitment. Drawing from his experience and common mistakes observed, Lance provides practical tips on avoiding overly rehearsed or jargon-heavy pitches, suggesting instead to focus on conveying the unique value proposition plainly and compellingly. He highlights the versatility of elevator pitches across various contexts, from investment pitches to hiring and product sales. Throughout, Lance shares examples to illustrate key points, including how to structure a pitch, the significance of opening questions, and the importance of practicing pitches to ensure they are understood and engaging. Read the article https://ftb.bz/105BWatch the video https://ftb.bz/105VTalk to Lance about your startup https://ftb.bz/advisingSubscribe to Boot Prints https://ftb.bz/join 00:00 Introduction to Crafting an Impactful Elevator Pitch00:59 The Essence and Purpose of an Elevator Pitch02:12 Applying Elevator Pitches Beyond Investment02:45 Common Mistakes in Crafting Elevator Pitches04:15 Effective Strategies for Engaging Elevator Pitches07:28 Crafting Your Elevator Pitch: A Step-by-Step Guide10:46 The Importance of Practice and Feedback
This podcast is tailored for startup founders looking to enhance their negotiation skills. It emphasizes the importance of negotiation in various aspects of running a business, including dealing with investors, vendors, customers, employees, and co-founders. I know that many founders may lack experience or feel conflict-averse, so here I share practical advice and strategies to turn negotiations from potential conflicts into win-win situations. In the episode I discuss understanding everyone's needs and priorities, adopting a collaborative and creative approach, and aiming for equitable outcomes to facilitate ongoing positive relationships. Read the blog https://ftb.bz/104BWatch the video https://ftb.bz/104V Get one-on-one advising https://ftb.bz/advisingSubscribe to Boot Prints https://ftb.bz/join Book Suggestions:Never Split the Difference https://amzn.to/3VTix4SNegotiate Anything https://amzn.to/4azwQA4 00:00 Negotiation Skills for Startup Founders01:40 Negotiation Challenges and Strategies03:26 Diving Deeper into Negotiation Tactics06:21 Framing Discussions and Preparing for Negotiations08:13 Adopting a Healthy Negotiation Philosophy10:00 Creativity in Negotiation: Finding Win-Win Solutions12:01 Conclusion
In this episode of Feel the Boot, host Lance Cottrell delves into the significance of understanding and presenting your startup's market size to investors through the concepts of Total Addressable Market (TAM), Serviceable Available Market (SAM), and Serviceable Obtainable Market (SOM). He emphasizes the importance of achieving a plausible market opportunity, critiquing the TAM, SAM, SOM methodology for its arbitrariness and complexity, and suggests a more dynamic approach through a bottom-up analysis. Cottrell walks through hypothetical examples to demonstrate how startups can realistically project their growth and market potential. He also covers common pitfalls in market size estimation and offers insights on how to conduct effective market research, ultimately guiding founders toward a more credible and compelling representation of their market opportunity to investors. Read the blog https://ftb.bz/103BWatch the video https://ftb.bz/103VSubscribe the newsletter (for free office hours) https://ftb.bz/Join The episode explaining why angels and VCs need such big exits https://ftb.bz/92V 00:00 Unlocking the Secrets of Market Size in Your Startup Pitch00:33 Welcome to Feel the Boot: Navigating the Startup Journey01:09 Why Market Size Matters to Investors02:29 Decoding TAM, SAM, and SOM: The Basics04:09 Common Mistakes in Market Size Presentation05:39 A Real-World Example: The Acme Clothing Company08:19 Bottom-Up Analysis: A More Accurate Approach09:36 Finding the Data: Tips for Accurate Market Analysis14:56 Presenting Your Market Size: A Strategic Timeline Approach20:49 Conclusion and Next Steps
Testing Startup Ideas and Assumptions ⚖️ John Li of PickFu Interview In this interview, John Li, the co-founder of startup PickFu, discusses the innovative concept of his company as a digital focus group for businesses. He walks us through their transition from a physical product to a software solution after observing a growing need for unbiased design feedback. John also shares interesting customer success stories attributing to their product's efficiency. He emphasizes on the importance of regular testing in business and discusses their company's decision to employ a fully remote work model, the challenges faced, the tools used, and the benefaction of current technology to their work. Towards the end, John yields advice for aspiring entrepreneurs on testing and patience in realizing a startup's success. Read the transcript https://ftb.bz/102BWatch the Video https://ftb.bz/102VFollow John on LinkedIn https://www.linkedin.com/in/johnliFind PickFu at https://PickFu.com PickFu.com discount code FEELTHEBOOT for 50% off your first paid test. Guest Bio:John Li is the co-founder of PickFu, a consumer research platform for getting instant feedback from target audiences. Thousands of global brands rely on PickFu to help them make better data-driven decisions about their products and marketing. John is passionate about building systems that help others succeed. He has degrees in computer science from UC Berkeley and the University of Washington. John and his family live in the San Francisco area, where he shuttles his kids around in his dream car (a minivan).
In this discussion, Michael Regnier, founder of Sales Design & Delivery, shares vital insights into sales strategy tailored for startup founders, particularly those with a technical background. He explains that a company's sales strategy must encompass every aspect of the go-to-market message, including the target audience and the route to reach them. Smith articulates the importance of defining value propositions, pricing, and delivery models while underlining the necessity of iteration. He emphasizes the need to think from the customer's perspective and pitches the idea of 'if I were you selling'. Smith discusses adopting a sales strategy that proves one's belief in their product, building credibility for the customers. He also covers key points like avoiding paralysis and the significance of designing and delivering the sales process in a controlled manner for effective market feedback. Mike Regnier has been an executive sales manager for small companies for twenty-five years and has helped many entrepreneurs "crack the code" in unlocking their rapid and sustained growth. As a result of his successful exits, he was encouraged by several Private Equity and VC groups to create Sales Design & Delivery, his sales-scaling consulting firm, in 2012 and has been helping small companies achieve their potential ever since.
In this milestone episode, host Lance Cottrell dives deep into several critical topics inspired by his recent heart attack. First, he compares a heart attack with a financial crisis in a startup, emphasizing the need for recognizing early warning signs and taking immediate actions. He discusses how to identify critical situations where your venture is at risk and how to handle them effectively while sharing his personal experiences with his own startup. Then, he talks about the need to reassess one's priorities and the importance of aligning personal goals with the way we spend our time. He urges all founders to question their inherited societal goals and reflect on their passions. Lastly, as a public service announcement, he shares early warning signs for heart attacks and strokes, drawing parallels between them and potential dangers facing startups. He ends by stressing the urgency of immediate medical attention and action in such health crises. Read as an article https://ftb.bz/100BWatch the video https://ftb.bz/100V Schedule advising with Lance https://ftb.bz/Advising US Government Subsidized Health Insurance https://www.healthcare.gov/
Startup Fundraising Facilitators
Startup Privacy Policies
You're delivering your pitch deck ask slide wrong! What you should say instead.Learn the right and wrong thing to ask for.How to handle hard questions during your ask. I was listening to several founders deliver their pitches. Most of them did their “ask” wrong and seriously damaged their chances of success.In this episode, look at their mistakes and how they could improve this critical step in their pitches.You need to understand the whole angel and VC investment process. You pitch to get the next meeting, not for an immediate investment in your startup. Read this as an article: https://ftb.bz/95BWatch the video: https://ftb.bz/95V Subscribe to Boot Prints: https://ftb.bz/JoinGet Advice for Your Startup: https://ftb.bz/Advising
Escape the Startup Paradox
Branding is far more than just a logo and color scheme.Learn how to leverage both positioning and branding in your startup buisiness In today's fiercely competitive business landscape, effective branding and positioning strategies are crucial for startups to stand out from the crowd. However, many founders underestimate the true scope and importance of these concepts. In this interview, we heard valuable insights from branding and positioning expert Mara Rada, shedding light on why these elements are vital for emerging companies. By understanding the multi-faceted nature of branding and the emotional factors that drive purchasing decisions, founders can create stronger connections with their target audience, ultimately leading to long-term growth and success. In the interview, Mara mentioned a few resources that will help founders learn more about branding and positioning:- 42Courses.com has many lessons on these and related topics. - Anything written by George Tannenbaum formerly with Ogilvy, and R/GA https://www.linkedin.com/in/georgetannenbaum/- Anything written by Manoj Jacob Creative Director at Crayons. Formerly at Ogilvy, DDB Mudra, Soho Square, & Havas https://www.linkedin.com/in/jacobwriter/ Get this as an article: https://ftb.bz/93BWatch the video: https://ftb.bz/93V Join Feel the Boot: https://ftb.bz/JoinGet advising from Lance: https://ftb.bz/Advising Mara Rada is a feral thinker, a brand whisperer, and a category positioner. She helps companies create the beast brands of the future without selling their souls. She has worked with some of the world's most remarkable startups, Fortune 500 corporations, and the world's best advertising agencies (Ogilvy). She is also a veteran public speaker and keynote presenter who talks about topics such as brand naming, category design, perceptual positioning, and nin-cliche-istic branding. She is the founder of FERAL, a strategic consultancy that specializes in untamed thinking and identity commercialization. Mara is not a guru and detests the word. Maybe as much as the dreaded “digital transformation”. But she sure knows how to transform lemons. https://LinkedIn.com/in/mararada https://ThinkFeral.com
How to create an angel investment portfolio for maximum returns.Learn what drives the returns for your angel investments. Read this as an article: https://ftb.bz/92BWatch the Video: https://ftb.bz/92VSubscribe to BootPrints: https://ftb.bz/JoinAngel Investing 101 series: https://ftb.bz/angel In episode, I delve into the economics of angel investing, emphasizing the need for a significant number of investments to increase the chances of success. Research shows that most angel investments result in losses or minimal returns, but a small percentage can yield substantial profits. To improve the likelihood of hitting those winners, you should make at least 20 angel investments. Diversification across different sectors is also crucial to mitigate risks associated with market fluctuations and sector-specific downturns. I then discuss the importance of planning an investment budget. Startups typically prefer pre-seed investments of at least $25,000 to avoid numerous small investments on their cap table. For investors with smaller check sizes, you might explore options like crowdfunding or syndicates. Syndicates involve a lead investor selecting an investment, while crowdfunding platforms allow for lower minimum investment requirements, enabling diversification through multiple smaller investments.
Non-monetary Startup Rewards and Recognitions.Eight employee incentives that work better than cash. In this episode of "Feel the Boot: The Science of Startups," I, discuss seven highly effective motivators and rewards for employees that founders can use to attract and retain top talent. These motivators include having a strong vision, giving employees equity, providing public recognition, delegation and employee empowerment, giving personal attention, tailoring rewards to the individual, and unique “wow” rewards. I emphasize the importance of understanding what motivates individual employees, as what works for one may not work for another. I share two examples of "wow rewards" that have had a significant impact on employees, such as handmade plaques and giving solid gold coins to employees who have put in a "gold medal performance." Access all my content on Running your Startup https://ftb.bz/running Get this content at an article https://ftb.bz/91BWatch the Video https://ftb.bz/91V Sign up for advising https://ftb.bz/advising
How to quickly eliminate the losers,and identify companies worthy of further due diligence. As an angel investor, you will need to look at many startups.This guide provides a framework for quickly analyzing deals to see if digging deeper is worth your time. This is part of a series on Angel Investing https://ftb.bz/AngelSubscribe to Boot Prints and access office hours https://ftb.bz/joinLearn about advising from Feel the Boot https://ftb.bz/advisingWatch the Video https://ftb.bz/90VRead as an article https://ftb.bz/90B Make a Quick First CutIs the Company Angel Investable?CompetitionValuationProblem/Solution ValidationBusiness EconomicsDefensibilityIntellectual PropertyNeed for Additional FundingWhat is There?ChurnAssumption ValidationIs This Possible?(bonus) Team
Non-Dilutive Fundraising
Your earliest investors are probably unsophisticated.You must help them understand how startup investing works. When you are at the idea stage, almost no angel or VC investors will back you, but people who know and care about you might.Unfortunately, this is usually all new and very confusing to them.You must ensure they understand what they are doing and paint a realistic picture of the possible outcomes.This video is for you, the founder. It explains your options for structuring the deal and how to communicate with them about this opportunity.I created another video to share with your potential investors that tells them what they need to know. https://ftb.bz/friends-and-family-explainer Read this as a blog: https://ftb.bz/88BWatch the video: https://ftb.bz/88V
Who decides what between the board and shareholders?How to handle the BoD and Shareholder meetings as a founder. Read the blog: https://ftb.bz/86BWatch the Video: https://ftb.bz/86V Get access to office hours and Boot Prints: https://ftb.bz/Join In this episode, I explain the board of directors and shareholders roles and responsibilities.Some votes require both groups to approve. Others are specific to the BoD or shareholders.Running shareholder and board meetings as a startup is easier than you think.Having those meetings is essential, even if you are the only participant!
VCs destroy more startups than they make unicornsLearn how to identify and avoid that trap The reason is the “marginal dollar problem”Understanding that will help you choose whether to accept venture capital investment with open eyes. Read the blog: https://ftb.bz/85BWatch the video: https://ftb.bz/85V Join Boot Prints for access to free office hours: https://ftb.bz/JoinMeet other founders in the Founders Alliance: https://ftb.bz/Alliance
My worst day as a founder
Fire the Founder?
Cofounder Vesting
Term Sheet Red Flags ☠️ Venture CapitalAbusive terms cause dilution, loss of control, & sabotage future dealsLearn what they mean and when to push back Read the article https://ftb.bz/78BWatch the video https://ftb.bz/78VFounders Alliance https://ftb.bz/AllianceMailing list for office hours https://ftb.bz/join Article on pre-revenue startup valuations: https://ftb.bz/66BArticle on why high valuations can be bad: https://ftb.bz/70B Here are the standard term sheets I mentioned:Y Combinator https://ftb.bz/Y-Com-TSNational Venture Capital Association https://ftb.bz/NVCA-TSAngel Capital Association https://ftb.bz/ACA-TS
Have you ever tried to deliver a pitch deck or other presentation, and the technology just won't cooperate? Either your computer won't talk to their projector, or there is some issue with the PowerPoint.How can you handle these situations in a way that leaves you looking as good or better than you would have if everything had gone perfectly?Video: https://ftb.bz/77VArticle: https://ftb.bz/77BJoin: https://ftb.bz/Join
Get more from your investor updatesWhat to include and an easy template Get the template here: https://ftb.bz/investor-update-template Watch the Video: https://ftb.bz/76V Get the podcast: https://ftb.bz/PodcastVisit the website: https://ftb.bz/Join the mailing list: https://ftb.bz/Join A regular investor update email is the best way to keep existing and prospective investors in the loop on your startup's progress.Use it to ask for investments, introductions, advice, assistance, and more.In this episode I share how to craft an update that people will read and will keep them engaged and supportive. Lance Cottrell has been an active startup advisor and startup mentor for over a decade.He has helped countless startups navigate the key decisions of their journey, like when to take venture capital investment and negotiating term sheets.He works with many companies in accelerators like Y Combinator and Founder Institute.He provides help with startup funding including raising venture capital and angel investment.He can help you achieve liquidity for your company at a high valuation.Feel the Boot is a startup vlog of tips and advice for early-stage founders.
Low on cash with no imminent funding?Here's how to keep your startup alive Read this as a blog: https://ftb.bz/75BWatch the Video: https://ftb.bz/75V Visit the website: https://ftb.bz/Join the mailing list: https://ftb.bz/Join When things get tough and cash is short, you need to manage your startup cash flow to survive. If things are particularly difficult, you might be forced to pivot or sell the company. Lance Cottrell has been an active startup advisor and startup mentor for over a decade.He has helped countless startups navigate the key decisions of their journey, like when to take venture capital investment and negotiating term sheets.He works with many companies in accelerators like Y Combinator and Founder Institute.He provides help with startup funding including raising venture capital and angel investment.He can help you achieve liquidity for your company at a high valuation.Feel the Boot is a startup vlog of tips and advice for early-stage founders.
What is a Cap Table?
Startup Survival
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