Playbook Academy

Simple playbooks for massive growth. One powerful growth playbook, delivered every Saturday morning. Acquire the mindset, tools, learnings and habits of elite entrepreneurs.

Writer

Saucey

Saucey is the leading e-commerce, compliance and logistics provider to regulated retailers. Powering safer and more convenient experiences for customers and retailers. 

We work with regulated retailers across 1,200+ cities to drive additional revenues, customers and provide insights/tools to help them manage their store online. 

Saucey also powers some of the world's largest brands to connect with and understand their end consumers, including Diageo, AB-InBev, Bacardi, Coca Cola, Constellation and more.

Highlights:
-Millions of happy customers across the U.S.
-Grown from $0 to hundreds of millions in sales
-Sent customers to the Super Bowl, Olympics, Adult Summer Camp and more
-Driven hundred of millions in incremental revenue to independent retailers 
-Built smart appliances that auto re-order beer
-Channing Tatum, Nick Jonas and more have all been delivery drivers
-Launched dozens of new brands into target markets

Founder & CEO

ROARKE

Roarke is an unlimited Design & Web Development subscription for the world's most ambitious brands.

Used by SaaS companies, Startups, DTC brands, Agencies, Franchises, and high-growth businesses to unlock their potential online. Roarke supercharges the design and development process, helping companies move faster and bring big ideas to life seemingly overnight.

Partner

Hampton

Hampton is a private, highly vetted community of high growth founders, entrepreneurs, and CEO’s.

Founding Member

Emjay

Emjay is a leading omni-channel cannabis technology platform.

In it’s first two years:
-Hundreds of thousands of customers served
-6 M&A transactions
-Grew from $0 to 7-figures/month in 6 months
-First native iOS application to sell cannabis in the app-store

textPlus, Inc.

textPlus is one of the largest texting & calling apps with over 70M users.

I oversaw US marketing/growth, user acquisition and CRM through digital and traditional channels. Including being one of the first/largest advertisers on Facebook's native ads platform (brand new at the time). Acquired millions of new users/month, tracking performance, executing & reporting against key KPI’s, and identifying channels that brought in higher LTV customers.

Helped plan our international launch. Oversaw all creative for advertising, marketing campaigns, and the textPlus brand.

Lead our ad sales platform, securing $millions in ad revenue from some of the world's largest brands.

Separately split out a small 6-person team to build an ultra low-cost international calling platform. Took it from concept / design / telco contracts to launch in 2.5 months.

Marketing Director & Head of Partnerships

Jarvus (Acquired by textPlus)

(Acquired by TextPlus) Jarvus was an iOS app that let people capture life's moments with their friends and family. It would analyze the geo-tags and time-stamps in your iPhone's photo album, match you with Facebook friends that were in the same places at the same time, and easily create group albums using you and your friend's photos. 

You could apply beautiful filters, effects and stickers to your content, and upload/share the collective "memories" / albums on Jarvus or across your social accounts. 

Featured on Jimmy Fallon. Celebrities shared moments with their friends and fans. TextPlus tagged us in a post on Jarvus that they wanted to acquire the platform. The rest is history.

Coupeez Inc

Coupeez was an early online deals platform unlocking customer savings across local businesses.  

-Lead product design and built the iOS and Android applications (very early app-store days). This is what opened my eyes to how mobile was going to change every business in the world.
-Designed our UI & UX for web, iOS, and Android from scratch. 
-Curated categories of deals and onboarded thousands of local businesses throughout California to our marketplace.

Head of Product

Over the past decade, I've built three multimillion-dollar businesses while growing a family and raising four children.

I started with no resources, no connections, and didn’t have access to the playbooks that would have made the journey 10X easier. 

As a kid, I made money garden landscaping for families at church, manufacturing merchandise for private clubs, and then developing websites and running ad campaigns for local companies.

By 21, I was founding companies. In the decade since, I've:

➤ Generated $300M+ in revenue
➤ Built operations in 1,000+ U.S. cities
➤ Served over 3 million customers globally
➤ Helped grow hundreds of small businesses
➤ Raised $30M+ in capital from Angels, VCs, Private Equity, and Family Offices
➤ Successfully navigated both successful and failed multimillion-dollar acquisitions
➤ Been featured in leading publications like Forbes, Bloomberg, Entrepreneur, USA Today and more
➤ Worked with and advised the world's most iconic brands, including Diageo, Mars, Tesco, 7-Eleven, AB-InBev, Molson Coors, and Constellation

BUT, the journey was hard (harder than it needed to be).

I’ve faced many of the things you don't think about when starting a company:

→ Fought off (and won) predatory lawsuits
→ Closed a Seed round days after my wedding
→ Negotiated with demanding government agencies
→ Worked with lobbyists to introduce or change legislation
→ Raised a Series A while in the hospital for my first son's birth
→ Navigated a failed multi-million dollar merger while my daughter was born
→ Survived near-extinction events where we had single-digit weeks or days to save the company

Personal interests: Boxing, strength training, being in the ocean, spending quality time with my wife Danielle and our four little ones.

———

👋 Follow me for daily tips on mindset, systems, lifestyle design, and high-growth habits.

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Chris Vaughn

Red Beard Ventures

We are an early stage VC firm looking to enable the future of the metaverse & develop frontier tech to better the world. We enable investors' access to new and emerging technologies and asset classes.
We look to both lead and follow in Seed/Series A/Series B investments, while enabling the future of Web3.0 by providing value to our portfolio companies through community development, native web3.0 partnerships, recruiting support, and strategic advisory.

Investor

Venture Partner

The Cap Table

A media company that teaches you everything you need to know to start angel investing.

Founder

LayerZero Labs

SpaceX

AngelList

Unstoppable Domains

Denarii Labs

The Tokenomics venture accelerator + token design and marketing consulting firm of Red Beard Ventures

Carta

FloQast

Account Executive 

Senior Business Development Representative

Business Development Representative

Deloitte Australia

Consultant

👋 Hi, I'm Elana Gold! Thanks for checking out my profile.

Here's what you need to know about me:

👉 Partner at Red Beard Ventures (RBV), a pioneering Web3 fund with over $25M in capital, investing in blockchain consumer apps, infrastructure, gaming, metaverse, and DeFi, both in equity and tokens.
👉 I lead the RBV Syndicate, which invests in startups at any stage and sector, with over 3,900 LPs, 210+ company investments, and over $50M deployed.
👉 An advocate for women in investing, I founded The Girls Table, a platform (for men and women) boosting entrepreneurs, creators, and investors through my podcast, Newsletter, and IRL events. My efforts have brought over 20,000 individuals into the investing space.
👉 My work has earned speaking roles at events like VeeCon, NFT NYC, NFT LA, and Consensus
👉 I have received Forbes 30 Under 30 and Business Insider's Rising Stars of VCs.
👉 As a CPA in New York, I combine financial acumen with a passion for innovative tech and community building.

If you want to learn more about investment opportunities, let's connect!

Hit 'connect' and send me a DM to kick off our conversation!

Twitter: www.twitter.com/itselanagold
Instagram: www.instagram.com/itselanagold
TikTok: www.tiktok.com/@itselanagold

Elana Gold

John Summit was 25, making $65K at Ernst & Young, & working 9am to 9pm on spreadsheets.

Today, he makes more in one show than he would have in his entire accounting career.

But he almost didn't make the jump.

In 2019 Summit saved enough to quit EY. 

His plan? Give music six months. If it fails, back to accounting.

His mom cried when he told her. "You're gonna become a DJ?"

Every safe choice was obvious:
- Stable $65K salary
- CPA credentials
- Clear career path to six figures
- Parents who finally stopped worrying about him

He quit anyway.

The timing couldn't have been worse. Five Miami Music Week shows lined up for 2020. The pandemic cancelled them all.

Back in his mom's Naperville basement. No income. No shows. Just a laptop and a dream to DJ.

Summit sent 100+ tracks to labels during lockdown. 99 rejections.

Track #100 changed everything. "Deep End" became Beatport's longest-running #1 of 2020.

His trajectory since:
- 2021: Beatport's #1 selling artist across all genres
- 2022: Launches Experts Only label, plays 132 shows
- 2023: Multi-million dollar Vegas residency (60 shows, 3 years)
- 2024: Madison Square Garden sells out in under 2 hours, headlining Coachella Sahara tent
- 2025: 50,000-person Experts Only NYC festival, nearly $1B in streams

Last year alone he made $22 million in tour revenue.

Summit posted: "I used to think I wasted so many hours studying accounting, getting my CPA and working in big four but now I realize it's what taught me the value of hard work."

The truth is... safe path isn't actually safe. It's just predictable misery.

Summit could've stayed at EY. Made partner by 35. Retired at 60 with a decent 401k.

Instead, he's 31, running a global brand, living a life that his accounting colleagues can't even imagine.

You know what's riskier than quitting your job to chase something you love?

Spending 40 years in a career you picked at 22 because it was "safe."

Partner at Red Beard Ventures | VC & Angel Investor

Two engineers. Same startup. Same role. Same start date.
One walked away with $2M. The other with $290K.

The difference wasn't talent, luck, or performance reviews.
It was one question.

When they got their offers, Sarah asked: "What percentage of the company is this?"
Mike asked: "When do they vest?"

Mike got offered 20,000 options. Strike price: $0.50. The recruiter said it was "competitive." He accepted on the spot.

Sarah got the same offer. But she did something Mike didn't.

She asked to see the cap table.

Those 20,000 options? Just 0.02% of the company. Sarah pushed back: "I want 0.1%."

The negotiation was brutal. The CEO said she was being unreasonable. Sarah almost walked. But she got her 100,000 options.

Fast forward two years. Series B closes. Everyone gets diluted 25%.

Sarah notices. Mike doesn't even know it happened.

Sarah books time with the CEO: "I'd like a refresh grant to maintain my ownership."

She gets 50,000 more options. Strike price: $3.00.

Year four. The billion-dollar acquisition at $15 per share.

Mike's take: 
20,000 × ($15 - $0.50) = $290,000

Sarah's take: 
- 100,000 × ($15 - $0.50) = $1,450,000
- 50,000 × ($15 - $3.00) = $600,000
- Total: $2,050,000

Seven times the payout. Same company. Same role.

But here is what you need to know.. Mike isn't unusual. He's the norm.

Next time you get an offer, don't celebrate the option count.

Calculate the percentage. Negotiate the percentage. Protect the percentage.

Because the difference between $290K and $2M isn’t luck.. it’s knowing your ownership and fighting for it.

Welcome back to The Cap Table Newsletter! This bi-weekly newsletter will share key insights on angel investing, start-ups, and investment opportunitie

Open article: You Received Start-up Options.. Now What? by Elana Gold • 5 min read

You Received Start-up Options.. Now What?

I listened to 3 hours of Naval Ravikant on Joe Rogan so you don't have to.

Here are the 7 lessons that stuck with me:

1. "You're not going to get rich renting out your time."

Naval grew up broke in Queens. Single mom. Got rejected from Dunkin Donuts. Had to borrow $400 just to go to college.

Even lawyers and doctors charging $500/hour aren't getting rich - their lifestyle ramps up with their income. They can't retire.

Real wealth = owning equity. A piece of a business. Code that works while you sleep.

2. Happiness is a choice.

Naval used to be miserable. Would rehearse conversations in his head to sound smart.

Now? He meditates in doctor's waiting rooms. Turned down business travel for 5 years straight.

His formula: "Desire is a contract you make with yourself to be unhappy until you get what you want." So pick ONE desire. Let the rest go.

3. "Specialization is for insects."

The Greeks and Romans started in school, went to war, ran businesses, served in government, then became philosophers.

Naval's point: Everyone should be able to do everything. Madonna and Paul Simon reinvent themselves with each album - their old fans hate it, but that's how you stay alive creatively.

4. The modern struggle is against your phone.

We're not built for this. Our brains can't handle world-breaking news 24/7 injected straight into our skulls.

Social media, sugar, video games - all weaponized by "people in lab coats" figuring out how to addict you.

You stand alone against billion-dollar addiction machines.

5. "If someone can tell you when to show up and what to wear, you're not free."

Doesn't matter if you're a Wall Street banker making millions. If you have a boss, you're not actually rich.

Naval's prediction: Within 50-100 years, everyone works for themselves. Wake up to five job offers on your phone. Choose your project. Work three months, then go to Tahiti.

6. "Peace is happiness at rest. Happiness is peace in motion."

What we really want isn't peace OF mind - it's peace FROM mind.

That's why we chase orgasms, extreme sports, and psychedelics. Trying to shut up the monkey mind for just one moment.

Pascal nailed it: "All of man's problems arise because he cannot sit by himself in a room for 30 minutes."

7. "Your real resume is just a catalog of all your suffering."

When you look back on your deathbed, you won't remember what you were given. You'll remember the sacrifices. The hard things.

If everything came easy, your life has no meaning. You need the struggle.

---

This podcast was from 6 years ago but it is still so relevant. 

The meaning of life? There isn't one.

You get to make your own. That's the gift.

taplio

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Chris Vaughn

Elana Gold

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