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In this Week's Newsletter

Latest Podcasts: What You Missed

The Week in Exponential Scale (In Case You Missed It)

Miss a few Daily issues while actually running your business? We’ve got you.

Here’s a quick skim of everything we shipped in the Daily newsletter last week.

Free Daily Drops

  • The Microteam Identity: Fixing Decades of Inefficiency Stop apologizing for your small team size and start embracing the competitive advantages that come from being lean, fast, and efficient while legacy companies drown in coordination overhead.

  • Automate Post-Purchase Follow-Up Sequences Turn every sale into a relationship engine with automated sequences that reduce churn, increase repeat purchases, and make customers feel valued—without lifting a finger after setup.

  • Content Repurposing: Turning 1 Piece Into 10 Write one blog post and systematically turn it into 10 pieces of content across every platform, maximizing your ROI on every hour you spend creating without sounding like a copy-paste robot.

  • Win/Loss Analysis: Learn From Every Deal Your lost deals are a goldmine of insight if you actually ask why you lost—run win/loss interviews to uncover what's broken in your sales process, positioning, or product before it costs you the next 50 deals.

  • 1440 Media: The $1M RPE Single-Channel Strategy Learn how 1440 Media hit $1 million in revenue per employee by ignoring every channel except email newsletters and proving that focus beats diversification every single time.

  • Free Tools That Actually Work (And Don't Limit You) A curated list of 33 completely free, open-source tools that don't hit you with paywalls when you hit user #4 or contact #501—build your entire microteam stack for $0/month if you're willing to trade setup time for cost savings.

Premium Daily Drops

The $0→$100K MRR Framework

$100,000 in monthly recurring revenue.

For most founders, that's the magic number. It's not "rich." But it's real.

It's:

  • Enough to pay a small team

  • Enough to reinvest in growth

  • Enough to stop worrying about payroll every month

  • Enough to prove you've built something that works

But here's the problem: Most founders don't know how to get there.

They know how to get from $0 to $10K. Hustle. Grind. Close deals manually.

But scaling from $10K to $100K? That's different. You can't just hustle harder.

You need a system.

Today, I'm breaking down the exact framework to go from $0 to $100K MRR, with real numbers, real stages, and real examples from founders who've done it.

The Founder Who Quietly Bootstrapped to ~$100K+ MRR: Calendly’s Playbook

Calendly didn’t look like a breakout SaaS in its early days.

When Tope Awotona launched Calendly, the company started with:

  • Founder-funded capital (largely self-financed)

  • A very small early team

  • A painfully simple MVP

  • Zero hype, zero press

For years, Calendly grew under the radar. Content and community company SaaStr has repeatedly cited Calendly as a textbook example of stage-aware, capital-efficient scaling.

Stage 1: $0 → Early Revenue

Focus: Prove people will pay

What Calendly did:

  • Solved one narrow, painful problem: scheduling friction

  • Charged early, even when the product was basic

  • Relied on founder-led feedback loops

  • Optimized for usefulness, not growth

This phase was about validation, not scale.

SaaStr’s recurring lesson shows up here clearly:
Revenue is the only real form of product–market fit.

Stage 2: Early Revenue → Repeatable MRR

Focus: Prove the sale repeats

What changed:

  • Refined ICP around professionals who lived in meetings

  • Standardized pricing and onboarding

  • Stopped edge-case customization

  • Let the product, not sales, do the explaining

Calendly leaned into self-serve early, which made repeatability possible without headcount.

Stage 3: Repeatable MRR → Scalable Growth

Focus: Prove acquisition can scale

What unlocked growth:

  • Viral, product-led distribution (every invite was marketing)

  • Word-of-mouth instead of paid sales

  • Continued focus on simplicity over feature sprawl

  • Deliberate resistance to hiring ahead of need

SaaStr frequently highlights Calendly here as a reminder that Product-Led Growth (PLG) can outscale sales long before sales teams are necessary.

Stage 4: ~$70K–$100K+ MRR and Beyond

Focus: Retention and expansion

Where leverage came from:

  • Expanding use cases inside existing accounts

  • Teams adopting Calendly organically

  • Upsells tied to workflow depth, not feature bloat

  • Extremely low churn driven by habit formation

By the time Calendly raised outside capital years later, it was already massively profitable and growing fast.

The Pattern Calendly Proves

As often cited by SaaStr, this lesson sums it up: What gets you to your first real revenue milestone is not what gets you to scale.

Calendly didn’t grind harder.
They didn’t blitz hire.
They didn’t chase vanity metrics.

They modified the playbook at every stage.

A Step By Step Playbook

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