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!

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Building Products Right: Essential Advice for Early-Stage Founders by Chad Perry 🚀

Building a tech product as a non-technical founder can feel like a daunting challenge. Should you hire a developer? Outsource? What about mockups, tech stacks, and budgets? 😰

In this episode of Feel the Boot, I sit down with fractional CTO Chad Perry, who’s worked with countless early-stage startups to navigate these exact challenges. Chad shares insider advice on:

✅ Why you should start with mockups (not developers).

✅ How to successfully outsource your tech development.

✅ When to hire a CTO, developer, or team—and how to decide.

✅ Tips for managing tech projects as a non-technical founder.

✅ Why focusing on your minimum viable product (MVP) is key.

This episode is a must-watch for any founder building a tech product, especially if you’re overwhelmed by the process or worried about costly mistakes. 💡

🔗 Connect with Chad Perry on LinkedIn: https://linkedin.com/in/perryonfire

📢 Join the conversation: What’s been your biggest challenge when building your product? Share your thoughts in the comments below!

💬 Resources & Links:

     •           Blog https://ftb.bz/114B

     •           Video https://ftb.bz/114V

     •           For help with fundraising, strategy, or messaging https://ftb.bz/Boost

     •           More running your startup videos: https://www.youtube.com/playlist?list=PLgMU_ie96T-I8qMi2th8SIuJfMjAkuyAe

Don’t forget to like, comment, and subscribe for more startup insights! 🚀

#startups #founders #entrepreneurship #techstartups #productdevelopment #FeelTheBoot

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Chad’s Bio

I help founders and CEOs plan, build, and go to market with B2B SaaS products.
But deep down I'm just a nerd who loves to code, market, and sell - and started a few tech companies. 
20+ years in tech and software development, started a few businesses, trained with the world’s top marketing coaches, now supporting founders and executive teams in product development and strategy.
If you want help starting or growing your tech business – connect with me on LinkedIn. https://www.linkedin.com/in/perryonfire/

Entrepreneur. Global citizen and former digital nomad. Closet hippie and probable hipster. Bicycle rider of the mountain and touring varieties. Former motorcycle rider. Aviator and pilot with a fascination for helicopters. Real life rocket scientist who's never built a rocket.

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. 🚀 Whether you’re a new founder or a seasoned entrepreneur, this conversation dives deep into the soft skills that are often overlooked but are crucial for scaling your business.

Emily shares her journey from a corporate career to becoming a fractional COO and creator of the “Leadershift” framework, where she’s helped thousands of business owners transform their leadership style. We explore topics like:

                  •               Why making assumptions about your team’s skills can cripple your business

                  •               How to transition from being a “doer” to a true leader

                  •               Practical strategies for delegating effectively (even when it’s hard to let go)

                  •               Finding the sweet spot between too much and too little process

                  •               The importance of play, rest, and variety for boosting creativity and avoiding burnout

Plus, Emily reveals her free business-owner assessment tool to help you understand your leadership style and where you might need to make some shifts for success.

Link to the assessment tool: https://learn.emilyhawkins4u.com/type/

Blog: https://ftb.bz/113B

Video: https://ftb.bz/113V

Fundability assessment: https://ftb.bz/fundable

Advising: https://ftb.bz/advising

Key takeaways:

Founders often lack management experience and need to learn team optimization.

Assumptions about team members can lead to significant business challenges.

Transitioning from doer to leader requires a shift in mindset and skills.

Different types of owners have unique strengths and weaknesses.

Processes and systems are essential for scaling a business effectively.

Play and relaxation can enhance creativity and problem-solving.

Founders must manage their energy and time to avoid burnout.

Creating a safe environment encourages open feedback and disagreement.

Trust and autonomy are crucial for team dynamics.

Self-awareness and personal development are key to effective leadership.

Bio:

Emily Hawkins is a seasoned business leader and the creator of LeaderSHIFT where Emily guides small business owners to implement strategies that not only keep more money in their businesses but also foster lasting success and growth. With over 15 years of experience in the corporate world—where she led teams, streamlined processes, and saved millions for large organizations—Emily made the pivotal decision in 2017 to leave the corporate sector and dedicate herself to helping small businesses thrive through her innovative approach. Equipped with a Supply Chain degree from the University of Tennessee, an MBA in Global Business from Georgia Tech, and a Robbins-Madanes life coaching certification, Emily has successfully coached over 2,500 individuals and business owners, guiding them to unlock their potential. Emily’s expertise and impact have earned her recognition, including being featured in Forbes in 2020 for her groundbreaking work. Emily believes meaningful changes in a business don’t require a fancy degree or technical know-how—just a healthy sense of curiosity and a willingness to adapt.

https://www.emilyhawkins4u.com

https://www.linkedin.com/in/emilyhawkins4u/

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/112B

YouTube https://ftb.bz/112V

BootPrints 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/111B

Video https://ftb.bz/111V

Subscribe https://ftb.bz/join

Advising https://ftb.bz/advising

How to Pivot Your Startup Before You Launch 🚀 Pre-Pivot Strategies for Entrepreneurs

In this episode of Feel the Boot, host Lance Cottrell dives into the concept of pre-pivoting for startups. Avoid the common pitfalls and wasted resources of traditional pivots by learning how to identify potential problems before building your product. Lance shares three effective ways to foresee issues, focusing on customer conversations, systematic testing of assumptions, and conducting a pre-mortem. Perfect for early-stage founders looking to navigate the complex journey of launching a successful business.

Blog https://ftb.bz/110B

Video https://ftb.bz/110V

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Advising https://ftb.bz/advising

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/109B

Video https://ftb.bz/109V

Newsletter https://ftb.bz/join

Advising 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/108B

YouTube https://ftb.bz/108V

Fundraising playlist https://ftb.bz/fundraising-playlist

Subscribe to BootPrints https://ftb.bz/join

Startup Failure Analysis 🔎 Key Lessons from Abby Sugar

In this episode of Feel the Boot, host Lance Cottrell delves into the startup journey of Abby Sugar, the impressive founder of PlayOut Apparel, a gender-equal apparel brand. Despite the brand's promising concept and innovative approach, it ultimately failed. Abby bravely shares her experiences and the unique challenges she faced, providing valuable insights for early-stage founders. Topics covered include founder mental health, team dynamics, investor relations, and the impact of external market factors. This in-depth conversation offers actionable lessons for anyone navigating the complex world of startups.

Abby Sugar’s Bio:

Having worked as a writer, editor, and independent personal trainer, Abby Sugar is a lifelong learner and taught herself about fashion, business and startups after studying English Literature in college. Abby is a graduate of Barnard College, Columbia University, and studied abroad at Hertford College, Oxford University.

To Abby, learning is everything, and her life motto is f*cking figure it out – so she set out to build the brand that she and her cofounders wish existed when they were younger. As an outgoing, unapologetically queer startup founder, she strives to be a leading voice in and for the LGBTQ+ community. Abby founded Play Out Apparel in 2018 with her cofounder, Grey Leifer. As Play Out's CEO, Abby:

- Graduated from the Founder Institute as a Select Portfolio Company

- Raised $750K in pre-seed from mission-aligned investors and secured loan opportunities

- Won $20K from the National Business Inclusion Consortium’s pitch competition and $10K from Alibaba and HelloAlice (chosen as 1 of 50 winners from 12,000 applicants!), as well as winning other pitch competitions

- Shared her story in the New York Times and Forbes

After an incredible journey, Abby closed Play Out Apparel in 2024 to pursue other opportunities as a startup founder, consultant, and investor.

Abby was named to the Forbes Next 1000 List in 2021, she speaks on podcasts, international panels, and gives frequent interviews about startups, fashion, diversity and inclusion, and topics important to LGBTQ+ individuals.

Be sure to SUBSCRIBE to Multitudinous Musings, Abby's monthly Substack Newsletter, where she shares general educational articles about startups and investing, longform journalism, and poetry/literature that she reads - it's also known as Sugar's Recommended Reading. https://abbysugar.substack.com

LinkedIn https://www.linkedin.com/in/abbysugar/

Instagram https://www.instagram.com/a.n.other.sugar

Blog https://ftb.bz/107B

YouTube https://ftb.bz/107V

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🚀 Why Startups Fail: Top 10 Mistakes to Avoid 🚀

🎥 In this podcast, I dive into the common pitfalls that cause most startups to fail within their first few years. Based on my decades of experience in the startup ecosystem, I share invaluable insights and practical tips to help you navigate these challenges effectively.

👉 What You'll Learn:

Market Needs: Understand how to validate the real demand for your product.

Running Out of Cash: Strategies to prevent running out of cash before hitting your key milestones.

Gaps in the Team: Tips on assembling a team that can pivot and adapt as needed.

Competition: How to stand out in a crowded market.

Pricing Mistakes: Aligning your pricing with the value you deliver.

Prototype to 1.0 Transition: Avoiding the pitfalls of technical debt.

Timing Your Launch: Identifying the perfect market entry point.

Maintaining Focus: Keeping your startup on track amidst potential distractions.

Go-to-Market Strategies: Ensuring you can reach your customers cost-effectively.

Co-founder Dynamics: Preventing conflicts that could derail your venture.

💡 Bonus Insight: Learn about "zombie corporations" and how to avoid becoming one.

🔗 Stay Connected:

📘 Read the full article for a deeper dive into each topic: [Link to article]

💬 Join our community discussion below and share your startup experiences and questions.

👍 Like, Subscribe, and 🔔 Ring the bell for more insights from Lance.

🌟 Whether you're a budding entrepreneur or a seasoned founder, this video is your guide to avoiding common startup mistakes and steering your venture toward success. Let's get your startup on the path to thriving, not just surviving!

#StartupAdvice #Entrepreneurship #BusinessStrategy #LanceCottrell #StartupSuccess

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