While breakout brands find unique ways to win, failed drinks startups repeat the exact same errors.1

Here are the 15 mistakes beverage startups make again and again:

Brand

1️⃣ Assuming taste is a moat: Great liquid is just the cost of entry, not a differentiator.

2️⃣ Confusing aesthetics with efficacy: One must understand that “good-looking” packaging does not equal good packaging.

3️⃣ Conflating appearance with brand: A brand is just a commodity with emotional appeal. A cool font on your label doesn’t do this heavy lifting.

4️⃣ Overvaluing IP: Your brand’s “cool” name, label, bottle, and website absent of sales is worth nothing.

5️⃣ Assuming versatility is an advantage: Leave versatility to products like duct tape and vinegar. Your brand needs to be dialed in when it comes to signature serve and occasion.

Sales and Distribution

6️⃣ Confusing distribution with brand-building: Getting on shelves isn’t the same as moving off them.

7️⃣ Chasing doors over velocity: Expanding your footprint before proving you can rotate off the shelf.

8️⃣  Neglecting execution because “the brand is killer”: A brand identity cannot rescue a broken supply chain or a sales team chasing a missing commercial value proposition.

9️⃣ Targeting “everyone” too early: Focus on a tight, passionate niche before attempting mass-market scale.

🔟 Ignoring trade spend: Underestimating the crushing cost of advertising and promotion (A&P).

Growth

1️⃣1️⃣ Underestimating cash conversion cycles: Paying for production months before retail buyers actually pay you.

1️⃣2️⃣ Hiring pedigree or experience over capability: Corporate resumes can sometimes clash with gritty, early-stage startup chaos.

1️⃣3️⃣ Failing to creating supply chain redundancy: Having only one co-packer means a single point of failure (or a mere delay) can capsize your inventory.

1️⃣4️⃣ Failure to benchmark: Not measuring your retail performance against hard, objective industry standards.

1️⃣5️⃣ Too many SKUs: One winning flavor beats five or six (that eat up capital, distract the sales team from what matters, and confuse consumers via the paradox of choice).2

When was the last time an AI tool told you that you got it wrong? If you’re anything like me, the answer is probably never.

My wife and I joke about the sheer sycophancy of AI. Whenever it tells us something we know to be patently false, we exclaim to one another that our AI just told us we invented some new form of mathematics.

But the business risk is no joke. Generative AI leans toward relentless optimism because positive validation keeps users engaged.1

The danger of this “agreeableness loop” is real. In 2025, researchers documented how chatbot sycophancy frequently sends users into “delusional spirals,” validating their wildest assumptions rather than correcting them.

I’ve seen far too many founders pat themselves on the back because AI offered encouragement instead of criticism:

• It praised velocity: It called a brand’s retail velocity “stellar” when it was actually dragging way below the category average.

• It hallucinated a moat: It told a founder they had a proprietary product, leaving them blind to a number of direct competitors already on the shelf.

• It ignored real-world margins: It validated a pricing model without factoring in the brutal reality of distributor cuts and slotting fees.

To shift generative AI from a passive enabler into an objective partner, one must stop asking for its opinion and start setting strict boundaries.

Here are 3 prompts that will turn AI from a patsy to a partner:

1. Demand Proof, Not Praise

   • Prompt 1: “Analyze my retail pitch. Show your reasoning, outline the counterarguments, and provide real-world citations for your claims.”

2. Stress-Test Your Moat

   • Prompt 2: “Act as a hyper-skeptical retail buyer. Tear my brand positioning apart and list three reasons you would pass on this product.”

3. Force the Real Math

   • Prompt 3: “Audit my COGS sheet. Assume a 15% distributor margin and 20% trade spend. Show me exactly where this pricing model breaks.”

Don’t rely on AI to tell you whether or not your idea is good. That’s what people are for; that’s what the market is for. You are not inventing new math.

Beverage distributor rejections are rarely personal. They’re governed by basic physics.

If you want your liquid to move, you have to respect the forces in the warehouse 𝘢𝘯𝘥 on the sales team:

• Gravity: Not the downward pull most people think of, but the law that massive objects attract smaller ones. In distribution, high-volume mega-brands have so much market “mass” they pull all of a distributor’s attention and resources into their orbit, leaving small brands starved. 🌌

• Inertia: Sales reps sell what’s already selling. They don’t push stationary boxes; an object at rest stays at rest. 🎱

• Momentum: Mass times velocity. A few early, high-profile retail wins build the speed needed to make reps want to ride your brand’s wave. 🎢

• Friction: Operational drag like messy pricing, out-of-stocks, or poor communication can literally slow your brand’s roll. 🛼

• Displacement: Warehouse space is finite. For your liquid to float, you have to explicitly show whose volume you are going to push out. The RNDC fallout is this concept in action. ⚓

Stop pitching abstract “potential energy.” Bring the the data that proves you have kinetic energy.

For a rep, a sale can easily be confused with success. But securing a placement, whether an endcap or a menu slot, is just the beginning.

Your brand doesn’t own that shelf space, so it’s imperative that you don’t treat an initial sale like a victory lap. It’s not difficult to find your bottles or cans evicted from the backbar, shelf, or cold case. Call it losing the placement, getting kicked off the menu, or hitting the clearance rack, churn is a beast. True partnership begins some time after the invoice is paid.

To protect distribution and turn one-off drops into permanent reorders, learn these 4 post-sale data points:

1. The Internal “Velocity Trigger” 🏎️

   Identify the exact lever, a menu pairing, a floor display, or a staff tasting, that triggers consumer depletion. Bain & Company research shows a minor 5% increase in customer retention can skyrocket profits by 25% to 95%. Finding this trigger prevents a “one-and-done” graveyard.

2. The Neighborhood’s Demographic Profile 🛒

   A college bar needs high-volume execution; a suburban boutique shop needs a deep backstory to justify a premium price. Learn the avatar walking through their doors so you can hand the account the exact script they need to sell it.

3. The Staff’s Honest Friction 🚩

   What do bartenders and clerks secretly hate about your product? Hard-to-pull corks? Awkwardly shaped boxes? Address it during onboarding. Don’t ignore their reality. A Brandon Hall Group study found that structured onboarding boosts user success by 82%. Treat the account’s staff like your own team; if they aren’t onboarded, they will quietly neglect your brand.

4. The Reorder Threshold 📊

   Every buyer has a mental breaking point or a corporately-mandated threshold. Find out exactly how many cases can sit on the floor before the buyer panics, and how low stock must get before a reorder becomes an urgent priority.

Most founders think they are fundraising, but simply asking for money is not the same thing.

Asking for money is a desperate and luck-driven transaction.

Fundraising is a strategic, skill-driven process.

Consider Hollywood: you wouldn’t pitch an arthouse film to Marvel Studios, nor would you pitch a slapstick comedy to Blumhouse.

Amateurs blast random inboxes via cold intros and pray for a lucky break.

Skilled fundraisers:

• target specific investors whose thesis is aligned with the enterprise,

• build relationships,

• and treat the pitch like a collaborative business venture. Why? Because it is.

Real fundraising requires a:

• Pipeline & Tools: Build a pipeline doc; here’s how. Track and score your targets using organized platforms like Airtable or AI-backed Google Sheets.

• Rigorous Cadence: Maintain a disciplined communication rhythm and follow-up strategy rather than relying on one-off interactions. The truth is: like selling, you are always fundraising. It doesn’t only begin when you’re raising a round.

• Complete Asset Stack: Build clean materials (email scripts, a one- pager, a teaser deck, a full deck, a data room) and always keep your contact info visible.1

Your brand doesn’t need explanation. It requires summarization. Preferably, in a single breath.

If your brand can’t be summed up in a single sentence, you don’t have a brand.

Chef Mario Carbone explains how Major Food Group scaled to 40 venues by anchoring everything to a singular narrative.1

For their flagship, Carbone, the experience leaves zero ambiguity. A diner leaves saying exactly one thing:

“I had dinner on a Martin Scorsese set and ate a veal parm the size of a hubcap.”

Here’s how that translates to the world of beverage:

• Carbliss: “I crushed a zero sugar, zero carb vodka seltzer in the backyard without getting bloated.” 🍋🏋️‍♂️✨

• Liquid Death: “I drank mountain water out of a heavy-metal tallboy can that looks exactly like a craft beer.”

• Corona: “I shoved a lime into a clear glass bottle on a sunny beach and completely forgot about my job.”

• Red Bull: “I slammed a tiny silver can of liquid adrenaline that made me feel like I could skydive out of a helicopter.”

No one is reading your brand guidelines.2 Sorry.

Your team wants a sentence.3

Your customers need a sentence.

Your consumers won’t understand more than a sentence.

No textbook can teach you what it actually feels like to walk into a slammed bar with a heavy sample bag, or how a single calendar shift can tank your monthly quota. The best advice comes from other reps, buyers, and bartenders who survive the daily grind.

Culled from the archives of Reddit, here is the collective wisdom for the next generation of wine, beer, and spirits salespeople:

1. On Integrity and Deadlines

“If you say you’re going to deliver something (a physical product, a price inquiry request, or any deliverable) and end up not being able to, then get that communication out as soon as you know, and own it. Fix it if you can, but don’t just say nothing and miss a deadline.” - Source: r/beer Thread

• The Lesson: Trust is built on predictability, not perfection. Bad news delivered early is an opportunity; bad news delivered late is a broken relationship.

2. On the Math Behind the Hustle

“Read up on sales days and calendar impact so you’re not caught off guard by swings in your sales vs last year. For example, March 2017 started on a Wednesday, ended on a Friday, and had 23 sales days. March 2018 starts on a Thursday and ends on a Friday, but it only has 22 sales days. Ignoring other factors like weather, that lost trade day will make it ~4% harder to meet last year’s numbers.” Source: r/beer Thread

• The Lesson: Understand the calendar. Data will protect your sanity when the raw volume numbers don’t seem to add up.

3. On the Golden Rule of Field Timing

“For god sakes don’t go in and try to sell something during peak hours, avoid lunch time and dinner time... going in during lunch is rude and virtually guaranteed not to work.” Source: r/bartenders Thread

• The Lesson: Read the room. If a buyer is drowning in service, your pitch is an active annoyance. Guard their peace and they will respect your pitch.

4. On Doing Your Homework

“Take time to walk the store/look at the wine list before you speak with the buyer. The last thing you need to do is, for example, present a Napa Valley Chardonnay when there are already 12 on the wine list.” Source: r/wine Thread

• The Lesson: Blind pitching is lazy pitching. Identify the shelf gaps before you ever try to make a rec.

5. On Being a True Consultant

“As you walk the store, check the back room, etc., take inventory of your own wines. See what’s moving well and what isn’t. Tell the buyer (e.g.) there’s only two bottles left of that case I sold you last time.” Source: r/wine Thread

• The Lesson: Your job doesn’t end when the case hits the backroom. Track the pull-through; solve their depletion problems before they have to ask.

6. On Detaching Your Ego

“If they don’t buy something on any given day, don’t take it personally. It’s not you they were rejecting, it was the wines.” Source: r/wine Thread

• The Lesson: A “no” is just a data point about a buyer’s inventory, budget, or current menu constraints. It is never a report card on your worth.

7. On the Power of Radical Honesty

“Don’t lie or make stuff up. If you don’t know something, just say so and circle back with an answer.” Source: r/wine Thread

• The Lesson: Buyers can smell manufactured answers from a mile away. Admitting you don’t know builds a foundation of credibility that a fake answer will instantly destroy.

Here’s what I’m reading this summer:

• The Devil Emails at Midnight: What Good Leaders Can Learn From Bad Bosses by Mita Mallick

• Up the Down Staircase: How Wine & Spirits Brands are Growing in a Declining Market by Ben Salisbury1

• Calling In: How to Start Making Change with Those You’d Rather Cancel by Loretta J. Ross

• Wine Marketing and Sales, Fourth Edition by Paul Wagner, Liz Thach, MW, and Susan DeMatei, CS

• Risk and Reward: How to Handle Market Volatility and Build Long-Term Wealth by Ben Carlson2

• Perfection by Vincenzo Latronico and translated by Sophie Hughes

What are you reading this summer?

The Bear is over. No spoilers, I promise.

I also promise that this is not a think piece; it’s merely an observation that supports an incredibly important lesson:

Good brands tell stories. Great brands become part of ours.

Carmy’s elite status in The Bear is anchored by his history at restaurant “brands” like French Laundry, Daniel, and Noma. The show’s gritty realism relies on Chicago staples like Pequod’s, Avec, and Kasama. These restaurants are elevated by being part of someone else’s story.

This mirrors how we use brands to anchor our own realities. Consider the psychological gap between saying, “We were out drinking,” versus “We were out drinking Don Julio.”

This reveals three foundational points of modern branding:

• The Power of Proximity: Organic cultural references establish far more authority than shouting your own narrative.1

• Identity Signaling: Consumers use specific brands as shorthand to telegraph their taste and status.

• The Cultural Lexicon: True equity means moving past transactions and entering daily vocabulary.

Years ago, I was party to extreme example of such a phenomenon. I was hauling boxes and cashiering in a liquor store when a customer asked if we sold Patrón. We didn’t. When I offered a number of other wonderful tequilas, she abruptly cut me off and said, “I don’t drink tequila. I drink Patrón.”

Patrón was part of her story. Tequila not so much.

I was at a backyard party in NJ last week. At 43 years old, I was the youngest person there. Yet, looking into the cooler felt like looking into the future:

• THC/CBD Beverages: Uncle Arnie’s, Howdy, & Houseplant

• Legacy Beers: Guinness, Amstel Light & Yuengling

• RTDs: High Noon & Surfside

• A lone bottle of Jagermeister

This cold box microcosm perfectly explains the shifting drinking habits of Americans over the last decade.

In one word: “Desolofication.”

We’re seeing the decline of the red Solo cup in favor of hyper-individualized drinking. We’re moving from the communal keg and events defined by a single liquid monoculture to highly personalized curation. Today’s beverage landscape mirrors the fragmentation of streaming television, Bowling Alone, and our hyper-personalized algorithmic feeds.

This is not a youth-driven trend. It’s middle-aged suburbanites swapping IPAs for weed sodas and tequila seltzers.

Desolofication explains:

• Hyper-Occasionality: We drink for a specific mood, not just out of habit.

• The RTD Rocketship: Single-serve convenience wins over bulky, multi-serve RTS formats.

• Convenience as King: Whether it’s the ascendancy of gas station/mini-mart as a shopping channel or the growing popularity of smaller format bottles, ease is non-negotiable.

• The Alt-Bev Boom: The rise of THC and premium Non-Alc proves social drinking no longer requires alcohol.

Gone is mimetic drinking behavior. Save for the occasion shot of Jager (or Tequila), we aren’t sharing drinks anymore. We’re curating our own flights. We just happen to be in the same backyard.

Restraint is a competitive advantage. Consider poet Elizabeth Bishop.

Over a brilliant 50-year career, she published only 101 poems.

Marvel at the math: that’s an average of just two poems per year. Yet her unrelenting focus, rigorous discipline, and absolute refusal to rush substandard work won her both the Pulitzer Prize and the National Book Award. 🏆

Drinks leaders and entrepreneurs could transform their businesses by acting more like Bishop.

It’s only when you aim for quality over proliferation, things grow (and, oddly, proliferate).

I’m not just talking about liquid quality, but:

• Relationship quality 🤝

• Process quality 🏗️

• Decision quality 🔀

• Data quality 📊

• Brand quality 🥫1

• Customer and Consumer quality 🛒

Here’s a link to a favorite of mine, Bishop’s “One Art.”

Sales reps require reinvention in order to stay relevant. Like certain pop stars—The Beatles and Madonna come to mind—successful salespeople evolve. This could mean fine tuning their presentation style or honing certain timeless traits. One’s market awareness must be constantly revised in light of changing tastes. Still, it’s better to develop a toolkit of skills that will allow you to adapt with the new economy. These skills, rather than product trivia, are often what need updating. After all, the ability to quickly find a payphone prior to order board cutoff is no longer in high demand.1 This brave, new world requires these eight, learnable skills that will help you level up your sales:

AI Literacy

• AI isn't going to walk into an account and sell a case for you, but it will save you ten hours a week on back-office admin. If you aren't using LLMs to synthesize market reports, clean up messy account lists, or instantly draft a custom pitch angle for a busy buyer, you are competing against a calculator using an abacus. Don’t harness the tech to create slop; leverage it so you can better understand your accounts and spend more time face-to-face. Learn about AI by reading a book like Co-Intelligence by Ethan Mollick and The AI-Driven Leader by Geoff Woods. Or take a free online class like Google Prompting Essentials.

Organizational Psychology

• Beverage sales are rarely a straight line between you and a single buyer. To survive, you have to navigate an ecosystem of competing incentives—the bartender’s ego, the GM’s margin panic, and the distributor’s inventory pressures. If you don't understand the psychological friction and internal politics inside an account, you aren't selling; you're just pitching. Learn how groups make decisions, find the real stakeholder, and solve their specific anxiety. If you want to master this, read The New Strategic Selling by Robert Miller and Stephen Heiman to learn how to map out who actually holds the power in an organization. Check out Never Split the Difference by Chris Voss to learn how to negotiate with others.

Data Analytics

• The era of the "relationship rep" who sells purely on a good lunch and a handshake is evolving. Some retailers might care about your golf game, but all of them care about cold box velocity and margin-per-square-inch. If you can’t open a spreadsheet, pull your own depletions, and read a market report to prove your brand's organic pull, you’re just guessing. Data is how you defend your shelf space from being swallowed by a competitor. Start arming yourself with knowledge and know-how now.

Social Media Literacy

• In late-stage capitalism, a fate worse than death is invisibility. For a brand or person, the shortest path to the latter is through social media ineptitude. Think of it as irrelevance by way of incompetence.

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  Contrary to the belief that you’re selling yourself, social media for salespeople is way of reminding others—your customers and your company—you exist. The more you “exist,” the easier your job will become. Mark S. Granovetter’s 1973 hypothesis on weak social ties might go a long way in explaining why likes, followers, and shares resonate and reverberate into sales.

• Writing

  You should know the difference between pallet and palate.2 You should be able to express yourself clearly. You should be able edit your company’s marketing blast so that it’s in your own voice. If you’re not actually talking with customer, you’re likely communicating with them via email or text. The ability to gain trust and respect by sounding authoritative is key.

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  How do you get better at writing? Read good authors. Write every day. Don’t like writing? Too bad. It’s a muscle that must be worked.

  As William Faulkner once quipped, “I only write when inspiration strikes. Fortunately, it strikes at nine every morning.”

  Read everything you write out loud. Change what doesn’t sound right. You can almost always edit at least 10%. Make every word work.

• Project Management

  Every sales rep needs to know how to manage their own time so they can be respectful of their customers’ time. Being organized is of utmost importance because this isn’t a business with cookie-cutter clients. Planning helps you deliver and delivering pays dividends.

  Text within this block will maintain its original spacing when published

  If you’re an executive or sale manager and you aren’t implementing agile sales it’s time you begin educating yourself. Your company, your salespeople, and your customers deserve it. It is time wine and spirit distribution learned something from the tech industry.

• Bilingualism

  If someone speaks another language, they will taste and talk of things you could never know. Download Duolingo and start learning.

• Graphic Design

  Reps need to be able to make their own simple graphics just like they’re expected to be able to carry 40 pounds. Salespeople need to know how to crop images, add text, and make collages. Canva is free and has just about all of the functionality that a rep could want. Level up your graphic design skills and never have to wait for anyone else to get back to you with that image you need.

In the film Awakenings, Dr. Malcolm Sayer interviews for a job after spending five years on an apparently failed research experiment.

When the board dismisses his hypothesis, stating “It can’t be done,” Sayer replies: “I know that now. I proved it.”1

In the best of circumstances, your brand makes money, lots of money.

Lacking growth or profitability, you must be proving something. And that thing that you are proving should be valuable.

Five things that are not valuable to prove:

1. 👅 Liquid tastes good (subjective noise)

2. 🎆 Influencer hype (vanity metrics)

3. 🚚 A distributor will list you (forced push)

4. 🪩 Flashy event activation (unsustainable)

5. 🗺️ Geographic expansion (any brand can grow their footprint)

Five things that are valuable for a brand to prove:

1. 🏎️ Reliable account velocity (organic pull)

2. 🔁 Repeat purchase behavior (customer retention)

3. 💰 Healthy gross margins at scale (unit economics)

4. 🍹 A clear drinking occasion (consumer intent)

5. ⏱️ A distributor rep can pitch it in 10 seconds (succinct, memorable, and distinctive messaging)

What are you proving?

The most important three words a drink brand, its sales team, or an investor can use are identical:

“Tell me more.”

In negotiation science, open-ended prompts act as behavioral crowbars. 🤝

While direct questions often put people on the defensive, inviting someone to elaborate safely bypasses their guard.1 It forces the speaker to fill the silence, organically exposing their true motivations, hidden anxieties, and strategic gaps.

From Socrates’ method of teaching ☝️ to Columbo’s strategy 🕵️‍♂️ for getting suspects to open up, “tell me more” gets to the heart of things:

• for Brands: It uncovers the raw, emotional “why” behind consumer buying habits during market research, moving past surface-level answers.2

• for Sales Reps: It diagnoses a retail buyer’s hidden operational pain points, margin pressures, and true category goals. 📦

• for Investors: It pressure-tests a founder’s core thinking and operational adaptability, cutting straight through a polished, rehearsed deck. 💵

Want to instantly kill an investor’s interest in your beverage brand?

Demand an NDA in your first or second conversation.

Your early-stage magic can’t be easily copied, but premature legal friction will absolutely kill your momentum.

When Red Bull launched, the recipe wasn’t a state secret; it was a slightly modified Thai energy drink. The magic wasn’t the liquid itself, but Dietrich Mateschitz’s genius marketing and guerrilla distribution strategy. These are things an NDA could never protect.

The usual concerns:

• “But what if they steal my formulation?” Remember, you shouldn’t share exact ratios or chemical specs in an introductory chat anyway.

• “What if a big brand steals my concept?” Investors fund execution, not a rival beverage startup built from a pitch deck.

• Your attorney will tell you to protect everything. But a lawyer’s job is to minimize risk; your job is to build a business.

Save the NDA or MCA for when it actually matters:

• Data Rooms: When opening up deep-dive financial and operational due diligence.

• Proprietary Specs: When sharing exact ingredient formulations or sensitive co-packer contracts.

• Finalizing Deals: When reviewing final contract terms, not during early relationship building.

A reader writes with a frustration shared by almost every supplier:

It’s crazy to realize our distributor reps have to work so hard just to get samples to interested accounts! How can we effectively get product into their hands?" It’s a vital question, because if your liquid isn’t actively in a rep's bag, your brand isn't going to sample itself.

Choosing a sampling strategy is a direct trade-off between scale, cost, and human connection.

Look at how William Grant & Sons and Steven Grasse's creative agency Quaker City Mercantile launched Hendrick’s Gin in 2000. Instead of relying on standard distributor fulfillment, they bypassed the traditional corporate pipeline by sending ambassadors to hand-deliver cucumber-laden "curiosity kits" directly to sales reps, accounts, and tastemakers. They knew a commoditized delivery system yields a commoditized response.

To solve this for your own brand, you have to choose your route:

• The Easy Route: Wholesaler Fulfillment

  This is what most suppliers do. Let the distributor handle logistics from warehouse inventory. While highly scalable, you completely sacrifice your message. Worse, you risk funding "ghost samples"—bottles that get lost in warehouse noise or end up in a rep's personal home bar instead of a buyer's glass.

• The Bespoke Route: Direct-to- Rep

  Gather rep home addresses and ship personalized sample kits and swag directly to them. It’s expensive and labor-intensive, but the high-touch impact ensures your bottle actually stands out and makes it into their bag. Note: this is might not be wise financially for a vodka that wholesales for $21, but for a high-margin, $90 luxury spirit, it might make all kinds of sense.

• The Hybrid Route: Face-to-Face

  Hand-deliver bottles yourself during market visits and general sales meetings. This builds instant rapport with zero shipping friction, though your footprint is strictly capped by your travel calendar. Although, who knows? The market just might benefit from your presence.
  

Too many brands over-index on the ends of the B2B pipeline while neglecting the critical center: the distributor rep. If your distributor reps don’t feel the magic of your brand, they can’t replicate it for their accounts.

How easy it is to forget that even the cheerleaders need cheerleading.

Transitioning your sampling from a standard logistics chore to a memorable, high-touch touchpoint is another way to turn potentially indifferent gatekeepers into high-performing frontline assets. Seeding samples in a way that is personal and distinctive is another tactic for building genuine rapport.

Ben Carlson is a favorite financial writer of mine.1 He seamlessly marries the anecdotal with data to illuminate and simplify arcane investment topics. In his recently published Risk and Reward: How to Handle Market Volatility and Build Long-term Wealth, Carlson combines stories of stand-up comedians prepping for talk shows with data-driven insights on soccer goal-keeping to illustrate the importance of smart inaction.2

In one of the most incisive sections of the book, Carlson outlines 20 things he believes about investing. I was struck by how much his investment philosophy parallels my own when it comes to entrepreneurship. Beverage brand founders would be wise to heed some of his takeaways:

Carlson: “…Simple beats complex. The problem is that simple is much harder to implement because complex will always sound more intelligent and appealing. It’s easier to be fooled by randomness with complexity.”

My view: For drink brands, simple is easier than complex—easier to manage, easier to message. It’s also less expensive than complex. Aim for fewer SKUs and fewer markets, done better.

Carlson: “…Self-control can make you far more money than just about any other trait as an investor. I know plenty of high IQ people who are terrible investors because they don’t have the right temperament.”

My view: Brands that scale require laser-like focus from their founders, leaders, and broader teams. Lack of focus is a pitfall I encounter time and time again. Brand creation and product invention is lighting a spark, while brand-building is growing the fire by continually gathering more and more fuel. It is dangerous for companies to conflate the two. Excitement needs to be sustained on a core product in a key market(s) for years.

Carlson: “…Process is more important than outcomes, but at some point performance matters. A successful investment process requires making good decisions over and over again. But you have to understand the difference between discipline and delusion if your process isn’t working.”

My view: In the early years, prioritize learning over raw volume. Strong velocity in ten accounts beats weak velocity in a hundred. Don’t confuse case counts with brand strength.

Carlson: “…There are many different paths to being a successful investor, but only a handful of ways to fail. There is no one-size-fits-all when it comes to investing the right way. But unsuccessful investors typically exhibit the same poor investment behavior…”

My view: I can’t tell you how your brand will succeed, but I can list the dozen or so ways your company will fail:

• undercapitalization

• lack of focus

• lack of product-market fit

• market/marketing dilution

• consumer confusion

• lack of differentiation and/or memorability

• mis-prioritizing goals

• not understanding the order of operations when it comes to brand-building

• not building a foundation that’s scalable

• poor company culture

• growing too quickly

• taking on the wrong investment at the wrong time

• not establishing commercial value proposition

There are no secrets or surprises here, just an unwillingness to come to terms with how difficult it is to nail these things down.

Carlson: “…Every investor has their own behavioral blindspots. Knowing your lesser self is more important than worrying about what other investors are up to.”

My view: Founders must be curious about themselves. Understanding your “lesser self” allows you to build the team that covers your gaps.

Carlson: “…Optimists are better investors than pessimists… If you don’t think things will be better in the future than they are today, what’s the point of investing in the first place?”

My view: You wouldn’t be building a brand if you didn’t believe in the bright future of this industry. Worry less about the macro headwinds and more about the microcosm that is the backbar you haven’t won yet.

Stop begging for “a quick intro.”

An often overlooked measure of success is the frequency of your unsolicited introductions. If your work is truly undeniable, people won’t just open the door, they’ll drag their best contacts through it without you asking. Excellence attracts advocates.

In 1947, Christian Dior didn’t have to lobby the fashion elite to notice his “New Look.” The designs were so disruptive that Harper’s Bazaar editor Carmel Snow famously grabbed him and declared his work a revolution. She didn’t wait for a pitch; she spent the next year introducing him to every power player in Paris because being the person who “found” Dior was the ultimate social currency.1

• Reputation as Collateral: People only volunteer intros when your excellence makes them look like a genius for discovering you. When a buyer introduces a sales rep to a peer, they aren’t doing you a favor, they are taking a risk. Make it worth it.

• Low-Friction Scaling: Volunteered intros bypass the “BS filter” and the gatekeepers that stop 90% of reps at the door.

• The Magnetism of Merit: No investor wants to use their social currency on a brand that hasn’t found its “why.” When your traction is undeniable, the intro becomes an opportunity for them to look like a visionary.

In 1736, London’s “Gin Craze” forced the spirits trade underground. To survive, vendors created the “Puss and Mew,” a wooden cat mounted on a wall where a passerby would whisper a code and drop a coin into its mouth. Gin wasn’t found on a billboard; it was found by those who knew exactly which alleyway to turn down.1 Today’s digital landscape has brought us full circle: discovery is no longer about who is the loudest, but who is whispered about in the right spaces.

Modern discovery has moved beyond “Google it.”2 For drinks brands, the path to purchase is now a funnel of ambient discovery and deep-niche validation. Here is where you need to show up:

1. The Top of Funnel: “Vibe” Discovery (TikTok & Spotify)

This is the new “front door.” Discovery here is passive and aesthetic.

• The Tactic: Don’t sell the liquid; sell the ritual, the vibe, the feeling.

• Examples: WhistlePig wins on TikTok with “edu-tainment” that feels like a creator’s post, not a brand’s ad. Non-alc brand Ghia uses curated Spotify playlists to own the “pre-dinner mindset” long before the bottle is opened.

2. The Mid-Funnel: The New “Sources of Truth” (AI Search & Reddit)

When curiosity turns into intent, consumers look for “unfiltered” data.

• AI Search: Search is shifting toward “answer engines.” Brands like Fortaleza Tequila and Foursquare Rum dominate Perplexity and Gemini results because they’ve seeded technical data across high-authority blogs and forums.3 Treat your mash bills, aging conditions, and ester counts as “training data.” If you aren’t publishing this data on high-authority sites like Substack or Medium, you are letting the AI hallucinate your brand story, or worse yet, ignore it.

• Reddit: In communities like r/bourbon, r/tequila, and r/rum, marketing fluff is a liability. You don’t “target” these users; you earn them. Host AMAs or share “behind-the-curtain” production secrets. If you provide raw value, the community becomes your most vocal sales force.

3. The Bottom Funnel: Conviction (Niche Apps & Dark Social)

This is where the actual purchase decision is codified by enthusiasts.

• Niche Communities: Platforms like Agave Matchmaker, Whiskybase or Rum Ratings are the final hurdle. A high score here is worth more than a dozen billboards because it offers peer-vetted “proof.”

• The Dark Social Layer: The most influential conversations in high-end spirits happen in “dark” spaces—closed Discord servers, WhatsApp groups, and Telegram channels. This is where “allocation hunting” and “bottle flipping” hype is born. You can’t buy your way into these groups, but you should be monitoring them.

Measuring Success

The old “cost-per-click” (CPC) metric is now a lagging indicator of an obsolete strategy. To measure modern influence, founders and marketing managers need to consider:

• Share of Model: How often does an AI “Answer Engine” recommend your brand when asked for a recommendation in your category?

• Sentiment over Volume: Don’t just track mentions; track the “authority” of the person mentioning you. One positive thread on a niche Discord is worth 1,000 “likes” from a broad audience.

• Data Density: Is your technical data (production specs, terroir, provenance) easily accessible and indexable?

Legend goes: Ernest Hemingway was challenged to write a story in just six words. He penned, “For sale: Baby shoes, never worn.”

Let that sink in.

Hemingway didn’t attempt to list an inventory of narrative components.1 He understood that a single, poignant image carries more weight than a catalog of facts.

In aggregate, the beverage industry, has never fully understood this.

Most product descriptions read like resumes, a collection of neutered facts:

“This wine is from Napa, made from Sauvignon Blanc by a second-generation grower.”

Fully accurate and completely forgettable.

To make a story more compelling, consider including the following three ingredients:

1. Relative Comparison: Use superlatives or scale to provide context. Is it the most or least something? Or the first?

2. Analogy/Simile/Metaphor: Give the brain a memorable mental shortcut.2

3. The “Who:” Connect the “what” to a human “why.” It could be about who the product is for or who made it. This is the “because” of it all.

Apply these techniques critically and note the wholesale transformation of our previously bland product story:

“This Sauvignon Blanc comes from the most biodiverse vineyard in California based on a UC Davis study. It was planted as a labor of love for the grower’s father, who refuses to drink the heavy reds Napa is famous for. She says crafting a delicate white wine in a region obsessed with bold Cabernets is like trying to play a solo flute in the middle of a heavy metal concert—you have to be technically perfect just to be heard.”

Facts inform, but stories stick.3 If you want your product to be more than a line item, stop selling the specs and start telling them better.