#26. Why the Second Sale is More Important Than the First

Upselling and Cross-selling: The Secret Ingredient for Boosting Revenue and Trust.

Apr 26, 2025

Welcome to the 26th free edition of More than Buzzwords—your weekly dose of sharp, no-fluff startup wisdom! ✂️

This week’s edition is all about what really works in today’s fast-paced world: authentic leadership, smart sales strategies, and building strong foundations.

Whether you’re a founder, operator, or team lead, this week’s insights will challenge your approach to work and business in 2025. It’s time to go beyond surface-level tactics and rethink how we lead, grow, and adapt.

Here’s what’s in store:
🔹 The Tweet Sheet – 4 tweets unpacking trust, sales as an experiment, the importance of upselling, and why most to-do lists are just organized chaos.
🔹 Startup Spotlight – Scapia is reimagining travel finance for young Indians—here’s how they’re changing the game.
🔹 BluSmart's Fall from Grace – The cautionary tale of a promising startup and why strong governance matters more than ever.

Building a startup can feel like juggling flaming swords—one wrong move and whoosh, it all comes crashing down!

Keeping everything in balance while growing a business? Definitely not a walk in the park.

But if you’re feeling the heat, don’t sweat it—you’re not alone! Whether it's rebuilding trust with your team, finding your market fit, or navigating the upsell maze, I’ve got you covered.

Keep reading for some fresh insights that will help you tackle the chaos and keep your startup on track!

The Tweet Sheet 📄🐦

We’re back with this week’s wisdom from the strategy and startup trenches of X.com.

Every Week I dig through the noise so you don’t have to — curating sharp takes from founders, operators, investors, and product minds who actually build things.

Whether you're scaling a startup, managing a team, or just thinking about work differently — these truth bombs will give you something to chew on.

Here’s what’s popping on the founder feeds this week: 👇

1. Loyalty Isn’t Dead. It’s Just Smarter Now. 🧠

@scotchisholm

Employee trust is at an all-time low.

And that’s on every leader.

We've swung from toxic hustle culture to "quiet quitting" and "bare minimum Mondays" in a heartbeat.

And honestly? I get it.

This isn't about laziness. It's about broken trust.

For years, employees have watched companies:

- Demand "family culture" while laying off thousands

- Preach work-life balance while texting at midnight

- Talk about transparency while hiding bad news

After decades of grinding themselves into dust, employees are drawing hard lines between work and life.

They're protecting themselves from getting screwed over.

Because employers have shown that they can’t be trusted.

That trust won't rebuild itself. As leaders, we need to:

Actually give a shit about our people

Connect roles to their purpose, not corporate BS

Invest in their growth

Give fair compensation tied to results

Create room for two-way feedback without fear

The days of expecting blind loyalty are over. And that's a good thing.

Great cultures aren't built on buzzwords and free snacks — They're built on mutual trust and respect.

Want your employees to care?

Show them you care first.

This tweet nails something we’ve all felt, but maybe didn’t know how to articulate — employees don’t quit because they’re lazy. They’re tired of being burned. They’re tired of being underpaid.

And honestly, who can blame them? Lately, we’ve seen too many companies demand "ownership" only to offer none in return. If you're leading a team — whether it’s 2 people or 200 — this is your wake-up call.

If you call your team “a family” when hiring someone, then remember to treat them like one when things go wrong.

Culture isn't perks or pizza parties. It’s what happens when things get hard. Build trust when you don’t need it, so it’s there when you do.

2. Startup Sales Isn’t a Funnel, It’s an Experiment 🧪

@jjen_abel

My shortlist of startup sales learnings over the years:

1. Product/market fit is (almost) always found in adjacent markets. Don’t handcuff yourself to Day 1 market vision.

2. You need to understand their buying process before you build/define your GTM.

3. Unlocking product/market fit is a process of elimination, NOT a hedge.

4. If the problem is not currently being measured or managed, it’s likely not a priority for the prospect, today.

5. The quality of your questions is critical for discovery; the quality of their questions is critical for intent.

6. Your niche is not a random starting point. It’s a GTM strategy to prove the experiment with Act 1.

7. Building a working GTM will take longer than building a working product.

8. Give yourself 18-24 months in the market to be invalidated, rejected, and redirected. Founders will also be "Head of Sales" for this period.

9. 80% of early sales is getting them excited by YOU, the Founder — how you see the world (vision) and how you uniquely solve their specific problem. Hint: the founder is the 'product.'

10. A seed-stage startup should never have a VP of Sales. Titles matter.

11. Never expect the user to sell to the buyer on your behalf — go direct to the buyer -- in many cases, users can be a blocker.

12. One of the fastest routes to shortening enterprise sales cycles is to turn the buyer into a user.

This is a distilled version of a long and very rich thread for founders — and honestly, it reads like a crash course in early-stage sales.

Most of us waste time chasing the wrong market, pitching to users who can’t buy, or trying to outsource conviction to a Head of Sales too early.

But here’s the thing: in the early days, you are the product. Not your deck. Not your GTM playbook. It’s your vision, clarity, and deep understanding of the buyer that moves the needle.

One of the points that stood out the most to me was: Never expect the user to sell to the buyer. In many cases, they’re a blocker, not a bridge.

It’s a mistake many early-stage teams make — assuming excitement from the user will naturally turn into a sale. But in enterprise sales, the buyer needs to hear it directly from you. Your narrative, urgency, and differentiation can make a huge difference.

If you're building a startup, read the full thread, and then read it again in 6 months. It'll definitely hit harder the second time.

3. Selling Once is Easy. Selling Twice is Smarter. 💸

@theonenicka

Upselling and cross-selling are an important component of raising revenue.

It’s infinitely easier to sell someone if they’ve already purchased something from you.
Momentum + trust are a powerful combination.

Amazon knows this all too well. Approximately 35% of their revenue comes from cross-selling and upselling alone.

This is even more important for smaller companies that don’t have an oligopoly on the market like Amazon does. If you’re looking to exit your business, don’t ignore these 2 factors.

More revenue → higher valuation → greater exit
Simple, yet difficult.

This tweet highlights a quiet but powerful growth lever that most early-stage teams sleep on.

Most founders treat upselling and cross-selling like side quests. But for any early-stage startup, this isn’t a “nice-to-have” — it’s your hidden growth engine.

We obsess over new user acquisition, but ignore the ones who’ve already said yes. That’s wild.

The first sale is trust-building. The second one is trust compounding.

This is when the existing users convince themselves — that they trust you, believe in the product, and want more of it. That’s where the magic happens.

Whether you’re SaaS or services, cross-selling isn't sleazy, it’s smart. Especially if you're bootstrapped or angling for an exit, this is how you punch above your weight on revenue and valuation. It’s not greedy. It's a good strategy.

4. Don’t List It. Solve It. 🎯

@hnshah

Most people start the week with a to-do list.

I start with a decision: What’s the one thing I refuse to let be a problem by Friday?

Not what should I do but what must be resolved.
The list doesn’t matter if the bottleneck stays. What’s yours?

This tweet is a simple mental unlock, but it shifts how you approach your entire week. Most to-do lists are just organized chaos.

This one question — “What’s the one thing I refuse to let be a problem by Friday?” — forces clarity and prioritization.

In startup life, the volume of tasks is infinite. But not all tasks are equal. This tweet cuts through the noise: it’s not about checking boxes, it’s about removing blocks.

Founders, operators, even mid-level folks juggling fire drills — try this next Monday. It’ll help you lead the week instead of letting the week lead you.

Also, check out my LinkedIn post on how your to-do list might be the reason you’re always busy—doing a lot, but somehow, it never feels like enough!

That’s all for this week’s tweet wisdom! Which one did you find the most impactful? Drop your favorite in the comments, I’d love to know.

Startup of the Week: Scapia 🚀

The credit card that wants to take you places—literally.

Today, we’re going to cover a growing startup called Scapia, which is emerging as a bold new player at the intersection of fintech and travel.

Scapia was founded by Anil Goteti, an ex-Flipkart senior executive who's no stranger to building products at scale. With Scapia, he's tapping into something most Indians want but don’t always plan for—travel.

His thesis? Indians are ready to explore the world, but financial products haven’t caught up. Scapia is here to change that.

At first glance, Scapia might look like just another credit card. But dig deeper and it’s clearly built with one persona in mind: the young Indian traveler.

Scapia offers a lifetime-free credit card (yes, zero joining and annual fees), co-branded with Federal Bank, and packed with travel-centric perks:

10% rewards on all purchases
20% rewards on travel bookings made through Scapia
Zero forex markup (massive win for international-travel-enthusiasts)
Unlimited domestic lounge access
And most importantly, no hidden costs

This isn’t just another plastic card, it’s a travel companion. And it doesn’t stop at rewards. The platform itself lets you book trips using your points.

You earn on the go, and spend on the go. No converting, no decoding—just seamless travel incentives baked into your spending habits.

Scapia is clearly chasing the Gen Z and Millennial crowd—the Instagram generation that values experiences over everything. And they’ve cracked the right formula: a zero-cost card with real rewards.

They’ve also gone big on brand-building. Scapia recently partnered with Royal Challengers Bengaluru (RCB) as their official credit card partner for the 2025 IPL season.

Their “Royal Entourage Bus” is a one-of-a-kind experience—selected customers get to ride to the stadium behind the official team bus and catch the match from premium seating. It’s smart experiential marketing that ties fandom with fintech.

Investors are rooting for them too! Scapia recently bagged $40 million in Series B funding, led by Peak XV Partners, with participation from Elevation Capital, Z47, and 3State Ventures.

This raise is crucial—not just to boost product offerings, but to scale up after a brief regulatory hiccup when the RBI tightened norms around co-branded credit cards.

With this new capital, Scapia is investing heavily in AI to personalize experiences, optimize credit models, and enhance fraud protection.

Wondering what the road ahead looks like for them? Scapia isn’t just building a card. It’s building a travel lifestyle brand that sits at the intersection of fintech and wanderlust.

The team has its eyes set on becoming the default travel finance partner for India’s upwardly mobile youth. From co-branded cards to travel loans, AI-driven offers to community-driven experiences—Scapia wants to own every step of the travel journey.

The tagline says it best: “The credit card that takes you places.”
Now they just need to keep the momentum (and partnerships) rolling.

While some startups are levelling up, others are unfortunately skidding off track. One such name in the spotlight lately? BluSmart.

It’s been all over the news lately. Keep on reading to see what I make of this cautionary tale (and the bigger lessons it holds). 👇

When Startups Lose Their Way 📉

The BluSmart saga and why clean governance is underrated

I’ve been hearing and reading about BluSmart’s downfall for a few days now—and honestly, I’ve been sitting with a mix of disappointment and disbelief.

Here was a startup that had everything going for it—timely product-market fit, a clean, tech-driven service that urban users genuinely loved, and a clear differentiator in a chaotic cab space dominated by Ola and Uber.

Zero cancellations, polite drivers, no surge pricing—BluSmart wasn’t just another app; it felt like the future of urban mobility.

And yet, here we are. Operations halted. 10,000 drivers asked to return their EVs. Users locked out of the app. Employees left unpaid. Founders under SEBI scanner for allegedly treating company funds like their personal piggy bank—golf sets, luxury apartments, the works.

It’s messy. It’s frustrating. But above all, it’s tragic.

The BluSmart story isn’t just about one company imploding. It’s a hard-hitting reminder for the entire startup ecosystem. A stark reminder that product alone doesn’t build a lasting business—governance does.

Behind BluSmart was Anmol Jaggi, also the founder of Gensol Engineering. And it’s this overlap that seems to have been its undoing.

Multiple reports point to financial irregularities, falsified documents, and misused funds at Gensol, which bled into BluSmart—both financially and reputationally.

What’s even more unsettling is the apparent opacity with which decisions were made internally. Senior leadership left in droves. Employees were abruptly shifted to WFH, only to be ghosted later. No clarity. No accountability.

Here’s the thing: Startup culture often romanticizes speed, hustle, and ambition. But no amount of growth hacks or investor decks can compensate for weak foundations. And no valuation is high enough to simply ignore ethics.

It’s easy to shrug this off as “another founder scandal,” but we really need to pay attention.

In an era of rising capital, increasing scrutiny, and maturing markets, trust is currency—with investors, employees, partners, and customers. And once that trust breaks, no PR campaign or pivot can fix it.

If there’s one big takeaway from the BluSmart saga, it’s this:
👉 Compliance is not boring. Transparency is not optional. Clean books and strong governance? They’re your moat.

Founders, the lesson here isn’t to play safe, it’s to play clean. Because markets do forgive failure, but they rarely forget fraud.

Let’s not just build great products. Let’s build companies that can stand the test of audits, headlines, and time.

What’s your take on this whole Blusmart Saga? 💬 Share in the comments!

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