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The Do’s and Dont’s of Pitching To Your Drunk Uncle At Thanksgiving

 

Thanksgiving is a time for gratitude, turkey, and… unsolicited advice from family members. As you pass the stuffing, the inevitable happens: your drunk uncle asks, “So, what exactly is this startup thing you’re doing?” Suddenly, you’re faced with the challenge of explaining your big idea to someone who thinks TikTok is just the sound a clock makes.
Whether you’re eager to share your entrepreneurial vision or simply trying to survive the dinner table discussion, there’s a right way—and a very wrong way—to navigate this conversation. In this blog, we’ll explore the do’s and dont’s of pitching your startup during Thanksgiving, ensuring that your business dreams don’t get roasted alongside the sweet potatoes. So, grab a glass of wine (but maybe not as much as Uncle Joe’s had), and let’s dive in!

Do’s:

  • Keep it light and simple.

Start with a casual approach. “Hey, Uncle Joe, I’ve got this cool idea…”

Keeping it conversational while approaching the subject is key to grabbing his attention. Your uncle doesn’t need a deep dive into your business plan or a lecture on market disruption. Use simple, relatable language to describe your idea. Instead of saying, “We’re leveraging AI to disrupt the logistics industry,” try, “We’re building a smarter way to get packages delivered.” Clear and concise explanations will resonate more than buzzwords. Remember to be prepared! StartupNV’s Executive Director, exited founder, and seasoned investor, Jeff Saling advises: “Perfect your elevator pitch. Attention spans will be especially short and split…. and have the deal docs and wiring instructions ready to send from your phone.”

  • Appeal to his interests.

Find something he can relate to.

Find a way to tie your startup to something your uncle cares about or knows. If he’s into sports, explain how your idea could help fans. If he’s a foodie, mention its potential impact on restaurants. Making it relatable will keep his attention and make your pitch more memorable.

  • Flatter him (a little).

Drop lines like, “You’ve always been good at spotting great ideas!”

Nobody likes a know-it-all, especially your drunk Uncle Joe. So, right when he seems to be dozing off from the conversation, ask him what he thinks of your ideas and leave space for him to share his. Bouncing ideas off of one another can make the exchange feel more natural and not one-sided. Make sure to listen to his ideas and “take” them seriously.

  • Let him know others are excited.

Tell him why everyone is going for seconds.

From seasoned investor, Joshua Curtis, here is some advice on showing excitement and spiking curiosity if your uncle is actually a savvy investor.

“As investors, we know that you love your stuffing, if you didn’t you wouldn’t be crazy enough to be a founder, but we want to see that everyone loves your stuffing too. Show us the demand! If you’re pre-revenue show us that you’ve done in-depth market research and have feedback from potential customers that they would purchase your product at your price. If you have revenue, show us metrics that indicate positive growth and adoption. Telling us your stuffing is the best is one thing, showing us through consumer interest and adoption is the best way to get us to grab our forks and get in line.”

  • Stay patient and flexible.

If he derails the conversation, gently steer it back or know when to pause.

With so much good food and good company, the conversation can certainly change every now and then. It’s important to know when to steer the conversation back to the topic and when to let the conversation flow on to the next, this can also be a chance to indulge in a second slice of pumpkin pie.

Don’ts:

  • Don’t get overly formal.

It’s Thanksgiving, not Shark Tank. Relax and match the vibe.

Pitching can be daunting whether it’s a room full of investors or during a networking event, but remember that this is a relative! There’s no need for a blazer, a slideshow, or corporate jargon about market penetration or scalability. Instead of diving into a stiff elevator pitch as though you’re talking to venture capitalists, take a moment to read the room. Your audience is family, not investors, and the Thanksgiving table is meant for laughter and connection—not a business boardroom.

  • Don’t turn it into a one-sided monologue

There’s nothing worse than feeling like you’re stuck in a never-ending lecture, especially at the dinner table.
If you dominate the conversation with a long-winded explanation of your startup’s mission, vision, and market potential, your uncle—and everyone else within earshot—might start tuning out. Thanksgiving is about sharing, not showboating. Instead, keep your responses brief and conversational, and let your uncle ask questions. The discussion will feel more interactive and less like a TED Talk no one asked for.

  • Don’t argue or get defensive.

If he says, “That’ll never work,” thank him for his thoughts and move on.

Chances are, your uncle might be unfamiliar with how your industry works but as your relative who wants to look out for you, he might be prone to pointing out the risks of your ideas instead of highlighting the positives. Make sure to avoid being defensive and instead, remind him that with great risk comes great reward.

  • Be careful not to over-stuff the offer just because he’s family. .

Know what your Ask is and be prepared with the deal terms you’re willing to offer ahead of time. You can find other ways to emphasize why this opportunity is special (early access to a high-potential investment).

Let’s hear from investor and StartUpNV’s Vice President, Madeline Feldman.
“Don’t promise equity in the family heirlooms as part of the deal, or over-promise equity just because you’re family. Blood may be thicker than water, but it’s not thicker than gravy. Remember to keep plenty of gravy for yourself and future investors. You can always share your riches with your family once you have them … (in cash!).”

  • DON’T Forget the Real Reason for Thanksgiving

At the end of the day, Thanksgiving is about gratitude and togetherness, not pitching your startup.

Be thankful that you have someone to pitch to, the opportunity to innovate, and a table full of great food to eat. If the conversation starts to derail or feel tense, pivot back to the holiday spirit. Approaching these moments with humor, patience, and perspective can turn even the most chaotic Thanksgiving pitch into a story worth sharing next year. You can hope, but don’t expect Uncle Joe to become your next investor.

Conclusion

Uncles are often wild cards; a single wrong move could turn your pitch into a heated debate about cryptocurrency at the kid’s table. As tempting as it may be to pitch your next big idea to your drunk uncle at Thanksgiving, it’s important to strike the right balance between enthusiasm and respect for the holiday setting. Remember, building support for your idea is a marathon, not a sprint, and the holidays are best enjoyed with laughter, good food, and meaningful connections.

Save the full pitch for a more appropriate time. Perhaps… during StartUpNV’s favorite day of the week, Pitch Day! Pitch Day happens every other Wednesday at the International Innovation Center in Downtown Las Vegas, and virtually from anywhere in Nevada,at 2pm. Catch the next one on December 4th, @ 2pm. You can also apply to pitch here.

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Founder Frights: 5 Kinds of Spooky Characters That Might Give You a Scare in the Startup World

1. “Zombie Startups: When It’s Time to Let Go”

Zombie startups shuffle through the world, neither dead nor alive, but definitely not thriving. If your startup is stuck in perpetual stagnation, it might be time to reconsider its future before you become one of the walking dead founders.

Zombie startups may still have some customers and are technically running, but they’re not growing or evolving. These companies often drain founders’ energy and resources without providing enough momentum to scale or succeed and are a major pain for investors looking to close out & right off the corpse. Learn more about key signs, how to call time of death on a startup, and stories of a few who double-tapped on the pivot to avoid becoming walking dead here.

Advice: Some rules of ZombieStartupLand to take with you…

Rule #7: Travel Light
“Heavy burn rates? Trim the fat—only the essentials survive the apocalypse.”

Rule #17: Don’t Be a Hero
“Sometimes the best move is to step back from your zombie startup and walk away.”

Rule #18: Limber Up
(Meme of a founder stretching) – “Always warm up. You never know when you’ll need to pivot… again.”*

Rule #22: When in Doubt, Know Your Way Out
“Have an exit strategy ready—zombie startups are known to hang on… and on… and on…”

Rule #31: Check the Back Seat
(Meme of a founder looking back nervously) – “Watch out for co-founders who suddenly resurface in zombie mode.”*

2. “Beware of Vampire Investors: Avoiding Bloodsuckers in the Startup World”

Just like a vampire needs fresh blood, some investors seem to feed on your hard work. They’ll offer capital but expect unreasonable control in return. Vampire investors drain more than they give—taking control of your company, demanding high equity and decision making power,, or offering unfavorable terms, with little strategic or network value, and not enough capital to justify the terms.Founders often accept blood-sucking terms out of desperation, but it can lead to a loss of control over the company and ultimately, its mission. Founder-friendly terms are one of the best indicators that your investors will be good team players in the light of day.

Key Signs:

Excessive Equity Demands: Investors asking for too much equity for the amount of capital they’re providing.

Overbearing Control Rights: Investors wanting too much control over board decisions or strategic direction, limiting founder autonomy.

Lack of Value-Add: They offer money but little to no strategic value, connections, or mentorship.

Advice:

Negotiate Smartly: Always seek a balance between capital and control. Try to negotiate terms where equity and decision-making remain in the hands of the founding team.

Choose Investors Carefully: Look for investors who offer more than just money. Opt for those who bring industry expertise, strategic advice, or valuable networks to the table.

Get Legal Advice: Have a good lawyer review term sheets and contracts. Don’t sign anything in haste just because you’re eager for funding. Once you let one blood sucker into your house… it’s hard to stop the bleeding.

3. “Frankenstein Founders: Piecing Together a Misfit Team”

Creating a team that doesn’t fit can lead to chaos, just like Frankenstein’s monster was a patchwork of mismatched parts. Building a startup is like assembling your dream team. But if you piece together co-founders and employees who don’t align in vision, skills, or values, you might end up with a monster instead of a thriving company.

Key Signs:

Conflicting Visions: Co-founders or key team members disagree on the long-term direction of the company.

Skills Gaps: Team members have overlapping strengths but leave critical skill gaps (e.g., no marketing lead in a product-heavy team).
Cultural Mismatch: A lack of shared values or communication styles can lead to misunderstandings and poor decision-making.

Advice:
Founders’ Alignment: Co-founders need to have clear, aligned goals from the outset. This includes both the vision for the company and the personal goals of each founder.

Complementary Skills: Build a team with diverse, complementary skill sets. Your early hires should fill gaps in your expertise, not duplicate strengths.

Culture Fit: Don’t underestimate the importance of cultural fit. Even if someone is highly skilled, if they don’t mesh well with your company culture, it can lead to long-term problems.

4. “The Curse of the Phantom Co-Founder”

 

A phantom co-founder is someone who vanishes when things get tough, leaving the remaining founder(s) to carry the weight of the company on your own. This can cause burnout and resentment, and damage the startup’s chances of success.

Everything seemed great in the beginning, but as soon as the going got tough, your co-founder disappeared like a ghost in the night. You’re now left haunted by their absence, but not the absence of their equity stake, while trying to run the startup alone.

Key Signs:

Lack of Commitment: Early signs might include a lack of follow-through on tasks, frequent unavailability, or a lack of enthusiasm for the company’s growth.

Avoiding Tough Decisions: When difficult challenges arise, the co-founder is nowhere to be found.

Focus on Other Projects: The co-founder may be more invested in side projects or their day job, treating the startup as secondary.

Advice:

Define Roles Early: Clearly define each co-founder’s role and responsibilities from the start. Everyone should know what’s expected of them.

Founder Agreements: Have a formal founder agreement in place that outlines ownership, contributions, and what happens if someone leaves.

Frequent Check-Ins: Regularly assess each other’s commitment and engagement levels. If a co-founder seems disengaged, address it early to avoid larger issues down the line.

5. “Don’t Get Trapped in the Haunted House of Bad Contracts”

Once you’re inside a bad contract, it can feel like you’re stuck in a haunted house with no escape. Bad contracts can haunt you long after they’re signed, with hidden clauses or unfavorable terms locking you into detrimental deals. This can apply to partnerships, vendor agreements, and even investor contracts.

You signed what seemed like a straightforward deal, but now you’re trapped by spooky clauses and unforeseen consequences. Don’t let your startup become the latest victim of haunted contracts!

Key Signs:

Overly Complex Terms: The contract is filled with confusing legalese that makes it hard to understand what you’re really agreeing to.

Hidden Clauses: There are clauses that grant excessive control or penalties that seem unreasonable or hidden in the fine print.

No Exit Strategy: The contract doesn’t allow for an easy way out, leaving you locked in regardless of future changes in circumstances.

Advice:

Read Every Word: Never sign a contract without thoroughly reading and understanding it, even if it feels tedious. Key details are often hidden in the fine print.

Consult a Lawyer: Always have a lawyer review any important contract, especially when it comes to equity, IP ownership, or long-term partnerships.

Negotiate Exit Clauses: Try to negotiate terms that allow you to exit or renegotiate the contract if things don’t work out as planned

Written by Madeline Feldman 

Founder Frights: 5 Kinds of Spooky Characters That Might Give You a Scare in the Startup World Read More »

When to Call Time of Death & How to Revive: Real Stories of Startup Pivots and Comebacks

Every founder dreams of success, but the harsh reality is that approximately 90% of startups fail. While failure isn’t always preventable, recognizing the warning signs early can help you either pivot successfully or make a dignified exit before exhausting all your resources.


The Tell-Tale Signs of a Failing Startup


1. Chronic Cash Flow Problems
You’re constantly worried about making payroll
Runway is shrinking with no clear path to extending it
Customer acquisition costs remain stubbornly high with no improvement in sight
You’re considering taking on high-interest debt just to keep the lights on


2. Market Indifference
Users aren’t as excited about your product as you are
Customer feedback is polite but noncommittal
Free users aren’t converting to paid customers
Your target market requires extensive education about why they need your solution

Turning Setbacks into Success: Inspiring Startup Pivot Stories

Every founder dreams of a successful startup, but statistics are sobering: nearly 90% of startups fail. Failure isn’t always avoidable, but noticing the warning signs early can open doors to a successful pivot or a strategic exit that preserves resources and reputation. Here are powerful stories of startups that turned things around with strategic pivots, and key takeaways for every founder.

The Instagram Transformation

Instagram, now a $1 billion photo-sharing app, began as Burbn, a complicated check-in app resembling Foursquare. But founders Kevin Systrom and Mike Krieger realized something critical from their users’ behavior: people loved the photo-sharing feature far more than any other. Here’s how they pivoted to success:

  • User-Centric Analysis: The team noticed users weren’t engaging with most of Burbn’s features. Instead, photo-sharing and filter options drove the most activity.
  • Bold Simplification: They stripped Burbn down to a single function—photo sharing—and enhanced the experience with easy-to-use filters and a clean, simple interface.
  • Results: Within weeks, Instagram saw massive user growth, catching Facebook’s attention and leading to a $1 billion acquisition in just 18 months.

Slack’s Leap from Gaming to B2B Communication

Slack is another powerful pivot story, emerging from the failure of a gaming company called Tiny Speck. Tiny Speck’s game, Glitch, struggled to gain traction despite millions in investment. But the company’s internal communication tool, created to help the team collaborate, revealed an unexpected potential:

  • Discovery of a Hidden Asset: While Glitch failed, the internal chat tool solved a pain point familiar to many companies.
  • Repackaging for a New Market: The tool became Slack, addressing a universal business need for efficient communication.
  • Results: Slack became one of the fastest-growing B2B companies, reaching a valuation of $7 billion within five years.

How to Execute a Strategic Pivot: Real-World Lessons

Stitch Fix’s Playbook for Market Expansion
Stitch Fix started as a styling service for women but scaled by carefully testing and entering new markets. Here’s how they grew beyond their initial niche:

  • Testing New Markets: They started small, piloting men’s clothing by using existing systems to gauge interest.
  • Gradual Expansion Strategy: With limited initial inventory, they gradually rolled out to select customers, using a waitlist to build demand.
  • Leveraging Core Strengths: Stitch Fix applied their algorithm-based styling to new segments while maintaining high-touch customer service.
  • Metrics and Feedback: Stitch Fix continuously refined its offerings based on customer feedback and tracked success through measurable metrics.

This deliberate, data-driven approach allowed Stitch Fix to expand to men’s, kids’, plus-size, and home goods markets, transforming it into a multi-billion dollar business.

Netflix’s DVD-to-Streaming Evolution

Netflix’s pivot from DVDs to streaming provides a masterclass in transition management. Although not a startup at the time, Netflix’s strategy highlights key steps for founders looking to pivot:

  • Parallel Operations: While DVDs remained profitable, Netflix gradually developed its streaming platform, using DVD rental data to shape streaming offerings.
  • Transparent Communication: Netflix was clear with users about the future, openly sharing updates and changes.
  • Strategic Investment: They built up streaming technology while still benefiting from DVD revenue and invested heavily in content licensing.

Today, Netflix’s streaming service dominates, but it was their careful pivot strategy that helped them make this transition smoothly and effectively.

Reid Hoffman’s Journey from SocialNet to LinkedIn

Reid Hoffman’s story shows that even a failed startup can provide the foundation for future success. Before founding LinkedIn, Hoffman launched SocialNet in 1997, aiming to connect people for both dating and professional networking. SocialNet failed within two years due to several factors:

  • Lack of Focus: SocialNet tried to be both a dating and professional networking platform but lacked a clear direction.
  • Timing and Execution: SocialNet was ahead of its time and couldn’t find traction.
  • Takeaways: From this experience, Hoffman learned the value of focus, timing, and the need for clear audience targeting.

LinkedIn went on to become the leading professional network, and SocialNet’s lessons were instrumental in this success.

Key Takeaway: Failure as a Learning Opportunity

Every failed startup provides lessons that can shape the next venture. Whether by pivoting smartly or learning from what didn’t work, the path of entrepreneurship is rarely straightforward. Embrace each lesson, use your insights, and remember—failure often marks the beginning of a new journey toward a much bigger success story

Owner Jeff Saling start up nv 1

Written by Jeff Saling 

When to Call Time of Death & How to Revive: Real Stories of Startup Pivots and Comebacks Read More »