Hang Around the Hoop Acquisition
Walk someone through the Tiny acquisition methodology, as described by Jeremy Giffin (Tiny’s first employee) and Shaan Puri. The framework is simple: be present, make low offers consistently, never take rejection personally, and set reminders to follow up. The 10% who eventually say yes are the deals.
When to Use
The user wants to buy a business — or is in the process of trying — and is struggling with sourcing deals or handling rejection. They might say:
- “How do I find businesses to buy?”
- “The owner said they’re not interested in selling”
- “I got turned down — should I move on?”
- “How does Tiny source their acquisitions?”
- “I keep reaching out but no one responds”
- “I found a business I love but they won’t sell”
The Core Principle
From Shaan Puri, describing Andrew Wilkinson’s method (7nWa1F3GJy4.md):
“He was like, ‘Yeah, I love that business, so I emailed them every month for like five years, and then finally one month they were like, Yeah, I’m willing to sell.’ That was the case for Letterboxd or Dribbble — he was just emailing the founder continuously. Aeropress, same thing — emailing the guy, ‘Hey, have you thought about selling this month?’ Some version of that question, hanging around the hoop.”
The hoop metaphor: in basketball, not every shot goes in. The players who score the most are the ones who keep showing up under the basket. In acquisitions, most sellers say no today. The ones who win are the buyers who are still there when the seller changes their mind.
Jeremy Giffin adds the counterintuitive corollary:
“If you send out a thousand cold emails, you’re going to get one or two responses from someone going ballistic. But the other 998 are either positive, no response, or neutral. It’s basically all upside.”
Step 1: Build a Target List (The Ongoing Pipeline)
Before you can hang around the hoop, you need to know which hoops to hang around. The pipeline is not a one-time list — it’s a living document you maintain forever.
Ask the user:
- What type of business are you trying to buy? (Industry, size, geography, business model)
- How many businesses of that type exist in your target market?
- Do you have a way to systematically identify them?
Ways to build the list:
- Industry directories and associations
- LinkedIn searches for owner/operator job titles in target categories
- Local business databases (Dun & Bradstreet, ReferenceUSA)
- Brokers who specialize in your sector (for off-market deal flow too)
- Attending trade shows in your target industry
Target list format:
| Business | Owner Name | Contact | Date First Reached Out | Last Contact | Status |
|---|---|---|---|---|---|
Build this list before you start outreach. Aim for at least 20-30 targets to create meaningful pipeline.
Step 2: Make the First Offer (Low, Professional, Non-Threatening)
The first contact is not a negotiation. It’s an introduction. Most owners aren’t thinking about selling — your job is to plant the seed.
The approach that works:
- Be direct but low-pressure: “I’m a buyer who focuses on [type of business]. I’ve been following yours for a while and would be interested in a conversation if you’re ever open to exploring options.”
- State who you are and why you’re credible (briefly)
- Ask a low-stakes question — not “what’s your price?” but “would you be open to a 20-minute call?”
- Make it easy to say no: “No pressure if the timing isn’t right.”
What not to do:
- Don’t lead with valuation or price in the first message
- Don’t send a long email explaining your entire thesis
- Don’t act desperate or oversell yourself
The goal of the first contact is a conversation, not a deal. Most people won’t respond. That’s fine.
Step 3: Handle the “No” (Without Ending the Relationship)
When a seller says no — or doesn’t respond — most buyers move on. That’s exactly wrong.
From Shaan, describing what happened when Tiny tried to buy Milk Road and the deal fell through:
“If I’m them, I’m thinking, ‘Hate those guys.’ But instead they were super professional about it. ‘Okay, no problem, sounds like you want to go a different direction.’ They hung around the hoop. A month later he says, ‘Hey, I didn’t see any announcement, like no deal went through?’ We said, ‘No, we decided not to.’ He goes, ‘Well, we’re still interested.’” — Shaan Puri
The rules for handling rejection:
- Thank them for their time
- Express genuine continued interest (“We loved what we saw — if your situation ever changes, we’d love to reconnect”)
- Do not burn the bridge or express frustration
- Log the rejection with a follow-up date
Ask the user: When you get a “no,” what do you currently do? If the answer is “move on,” change the system.
Step 4: Set the Follow-Up Cadence (The Automated Reminder)
The secret to hanging around the hoop isn’t persistence of will — it’s a calendar system.
“We made it a practice: whenever we’re buying businesses, A — don’t get personally offended when it happens, and B — schedule an automated reminder a month or three months later to just follow back up. ‘Hey, is there still an opportunity here? We still like the business, we liked it then, we like it more now.’” — Shaan Puri
The follow-up system:
| Status | Follow-Up Timing |
|---|---|
| No response | 30 days |
| Polite “not interested” | 60-90 days |
| ”Maybe someday” | 90-180 days |
| Active conversation (stalled) | 14-30 days |
| Post-deal-fell-through | 30 days, then 90 days |
The message at each touchpoint doesn’t need to be long. Jeremy Giffin describes what Andrew does:
“In terms of iterations, so many more iterations of just making something happen. Movement, especially when you’re an operator, creates information. You learn more by doing more things.” — Jeremy Giffin
A simple follow-up: “Hey [Name] — circling back from our conversation a few months ago. I still think [Business] is a great business and we’d still love to be a buyer if the timing ever makes sense for you. No pressure — just wanted to stay on your radar.”
Step 5: Move Fast When They Say Yes
The flip side of patience is speed. When a seller signals readiness, Andrew Wilkinson moves immediately.
“Not only does he move really fast when he’s excited about an opportunity, he’ll just keep texting you about it, or he’ll keep prodding until he finds out more information — he’ll fly to meet you right away.” — Shaan Puri
When a seller says yes or signals openness:
- Respond within hours, not days
- Propose a call within 24-48 hours
- Come prepared with preliminary diligence already done on their business
- Don’t play it cool — enthusiasm from a buyer is reassuring, not off-putting
Jeremy adds:
“The most successful people in the world respond instantly. I cannot believe how true it is. When you email the billionaire CEO it’s a 30-second response. When you email his vice president it can be a week.” — Jeremy Giffin
Quick Reference
| Step | Action | Key Principle |
|---|---|---|
| 1. Build pipeline | Create a living target list of 20+ businesses | Never stop adding |
| 2. First contact | Low-pressure introduction, ask for a call | Plant seeds, not offers |
| 3. Handle “no” | Thank, stay warm, don’t burn it | ”No today” ≠ “no forever” |
| 4. Follow-up cadence | Automated reminders at 30-90 day intervals | System, not willpower |
| 5. Move fast on “yes” | Respond immediately, fly if needed | Speed signals seriousness |
Search the Archive
grep -ri "hang around the hoop\|Andrew Wilkinson\|Tiny.*acqui\|Letterboxd\|Dribbble\|Aeropress" transcripts/
grep -ri "follow.*up.*seller\|cold.*email.*acqui\|persistent.*buyer" transcripts/
grep -ri "Dennis the Menace\|Jeremy Giffin" transcripts/
Output
After the session, deliver:
- Target list framework — the criteria for their ideal acquisition target, with a starter list if possible
- Outreach template — a first-contact message specific to their situation
- Rejection response — what to say when a seller says no, to keep the door open
- Follow-up calendar — specific dates and message cadences for each pipeline entry
- Pipeline tracker template — a simple spreadsheet to maintain the ongoing list
Source
Jeremy Giffin: Part Two — Best Business Opportunities Right Now — Shaan Puri interviews Jeremy Giffin, first employee at Tiny, on Andrew Wilkinson’s acquisition methodology.