Weekender #203

Over Labor Day weekend, I was at a girlfriend’s divorce party in Sonoma (mid-30s era is…something else 😂). Since I was already up north, I had zero excuse not to swing by INBOUND in San Francisco (thank you Carly from Hubspot for the invite!).

Conferences are always a mixed bag of networking, inspiration, and way too much coffee. Oh, and in this case, a Colin Jost comedy set that didn’t disappoint.

But the standout moment for me came during a session with Shaan Puri (co-host of My First Million; if you’re not listening yet, add it to your queue for spicy takes on business, trends, and money moves). He hosted a founder meetup where people pitched their companies…only for it to turn into a live pitch roast.

One founder explained how their product helps lawyers cut down on wasted time from free consultations (and not even in that straightforward of an explanation). Shaan paused and asked:

“Okay, so it saves time. But why do lawyers care about saving time? Because their time = money. Why not pitch it as: We save lawyers $50K a year by cutting free consults in half.”

And that’s the point: most people (even really smart, accomplished people) don’t walk into conferences with a pitch sharp enough to stick. Instead, they drown you in jargon or ramble through their company bio.

So, let’s fix that:

1. Start with the after Don’t lead with what you do; lead with what happens after. “I help small businesses double their client pipeline” > “I run a marketing consultancy.”

2. Answer the “why now?” test. If your pitch doesn’t make someone feel urgency, it’s forgettable. Tie your value to money, growth, or survival.

3. Anchor in a number. Numbers cut through noise. “We saved our clients 312 hours last quarter” is more memorable than “we streamline workflows.”

4. Curiosity > completeness. our pitch is a hook, not your TED Talk. Leave them with a “Wait, how do you do that?” instead of glazing over their eyes.

5. Run it through the cringe test. Say it out loud. If you’d feel embarrassed saying it to your childhood best friend, rewrite it.

This Weekend’s Challenge

When the classic networking question comes up (“So, what do you do?”) would your answer earn a polite nod…or genuine curiosity?

Not sure? Try this AI chain prompt to build your pitch:

1️⃣ Get interviewed first

“Act like a curious friend. Ask me 5 quick-fire questions to help me explain what I do and why it matters. Ask one at a time and wait for my answer before moving on.”

2️⃣ Draft the messy first version

“Using my answers, write an elevator pitch in plain, everyday language like I’m talking to someone at a bar, not a boardroom.”

3️⃣ Cut the fluff

“Now rewrite it in one sentence that would make someone at a conference say, ‘Wait, tell me more.’ No jargon. No filler.”

4️⃣ Turn up the volume

“Give me 3 punchy versions of this pitch: one bold, one playful, one no-BS straight shooter.”

5️⃣ Reality check

“Rewrite the version that feels strongest so it sounds natural for me to say out loud, not like a corporate press release.”

Because if Shaan can turn a bland “we save lawyers time” into a pitch that makes you want to invest, you can definitely sharpen yours before your next networking run 😉.

Joanna (TA Co-Founder)