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👉 Taking money from friends & family is easier — but is it worth it? Here’s what I’ve learned.
We raised investor funds for HappyBoards, and several friends & family participated. Having friends & family invest in your company is usually easier — they invest in you because they trust you. They know you, they believe in you, and they don’t need a 10-slide deck to say yes.
But it comes with a very high personal and emotional risk.
So why take money from friends & family? Because it’s just more fun. Building a company with people who are your biggest supporters creates an additional emotional connection to the business. When they have skin in the game, they root for you even harder.
But how do you actually ask them for money? That’s where things can get awkward. Having been through this once before, I knew that raising from friends & family wasn’t just about capital — it was about the emotional stakes. This time, I wanted to set expectations upfront so no one felt any pressure, no matter the outcome.
To make it easier, I came up with a lighthearted message to set the right expectations. Feel free to copy and use it as you need — and if it helps, pebble your version back to me! I'd love to see it!
I send this message after an initial conversation or when they they ask, "How much should I invest?"
— — —
👉 Should you invest in HappyBoards? Probably not. 😆
But if you're still reading, here’s my honest take…
Absolutely no pressure to invest in HappyBoards. These are exceptionally high-risk investments. If you’re considering it, here’s my straight-up, no-BS blurb:
1️⃣ Do not invest. Seriously. 😆 (But you’re still here, so let’s keep going…)
2️⃣
Share Dialog
👉 Taking money from friends & family is easier — but is it worth it? Here’s what I’ve learned.
We raised investor funds for HappyBoards, and several friends & family participated. Having friends & family invest in your company is usually easier — they invest in you because they trust you. They know you, they believe in you, and they don’t need a 10-slide deck to say yes.
But it comes with a very high personal and emotional risk.
So why take money from friends & family? Because it’s just more fun. Building a company with people who are your biggest supporters creates an additional emotional connection to the business. When they have skin in the game, they root for you even harder.
But how do you actually ask them for money? That’s where things can get awkward. Having been through this once before, I knew that raising from friends & family wasn’t just about capital — it was about the emotional stakes. This time, I wanted to set expectations upfront so no one felt any pressure, no matter the outcome.
To make it easier, I came up with a lighthearted message to set the right expectations. Feel free to copy and use it as you need — and if it helps, pebble your version back to me! I'd love to see it!
I send this message after an initial conversation or when they they ask, "How much should I invest?"
— — —
👉 Should you invest in HappyBoards? Probably not. 😆
But if you're still reading, here’s my honest take…
Absolutely no pressure to invest in HappyBoards. These are exceptionally high-risk investments. If you’re considering it, here’s my straight-up, no-BS blurb:
1️⃣ Do not invest. Seriously. 😆 (But you’re still here, so let’s keep going…)
2️⃣
3️⃣ How much should you invest? Take whatever number you had in mind… now divide it by 2. You’ll thank me later. If you get mad later, that’s a win.
4️⃣ Pro tip: If possible, invest from your IRA/401K for tax-free growth (not required, but smart). If you invest after-tax dollars, this investment also qualifies for QSBS, meaning if we hit big, your returns are federally tax-free (as long as you hold for 5+ years), and in some cases, state tax-free.
5️⃣ The upside? I’m swinging for the fences — playing for a 50x-100x return in 10+ years. We’ll explore early liquidity when it makes sense, but no rush. 90% chance we lose money, 9% chance it’s a moderate return, 1% chance it’s a breakout win.
6️⃣ Full transparency: Monthly updates, open chats anytime. No surprises. Any questions? Fire away.
7️⃣ If this sounds interesting, I’m happy to chat. No pressure, no hard feelings — just let me know. 🧀🚀
— — —
🚀 Founder Tip: If you’re raising from friends & family, set expectations clearly. They should invest because they believe in you, but they also need to be 100% comfortable with the risk — because no startup is a guaranteed win.
And yes, everyone always reacts to the "divide by 2" comment. That’s the whole point. 😆
Looking back, I wouldn’t change a thing. The responsibility of raising from friends & family never gets easier, but the journey feels more meaningful when you’re building with people who believe in you.
I Pebble You,
Ankit
"I Pebble You" is a heartfelt collection of thoughtful moments — articles, memes, videos, and insights —that spark joy and connection. Inspired by how penguins gift pebbles to their loved ones, it’s a space to pause, reflect, and share. Subscribe to receive these meaningful pebbles in your inbox, and add your own to help build something bigger — because together, we create more thoughtful connections.
👉 Read the previous pebble "Voice Notes: A Love Language🎙❤️"
👉 Read the original pebble "I Pebble You"
3️⃣ How much should you invest? Take whatever number you had in mind… now divide it by 2. You’ll thank me later. If you get mad later, that’s a win.
4️⃣ Pro tip: If possible, invest from your IRA/401K for tax-free growth (not required, but smart). If you invest after-tax dollars, this investment also qualifies for QSBS, meaning if we hit big, your returns are federally tax-free (as long as you hold for 5+ years), and in some cases, state tax-free.
5️⃣ The upside? I’m swinging for the fences — playing for a 50x-100x return in 10+ years. We’ll explore early liquidity when it makes sense, but no rush. 90% chance we lose money, 9% chance it’s a moderate return, 1% chance it’s a breakout win.
6️⃣ Full transparency: Monthly updates, open chats anytime. No surprises. Any questions? Fire away.
7️⃣ If this sounds interesting, I’m happy to chat. No pressure, no hard feelings — just let me know. 🧀🚀
— — —
🚀 Founder Tip: If you’re raising from friends & family, set expectations clearly. They should invest because they believe in you, but they also need to be 100% comfortable with the risk — because no startup is a guaranteed win.
And yes, everyone always reacts to the "divide by 2" comment. That’s the whole point. 😆
Looking back, I wouldn’t change a thing. The responsibility of raising from friends & family never gets easier, but the journey feels more meaningful when you’re building with people who believe in you.
I Pebble You,
Ankit
"I Pebble You" is a heartfelt collection of thoughtful moments — articles, memes, videos, and insights —that spark joy and connection. Inspired by how penguins gift pebbles to their loved ones, it’s a space to pause, reflect, and share. Subscribe to receive these meaningful pebbles in your inbox, and add your own to help build something bigger — because together, we create more thoughtful connections.
👉 Read the previous pebble "Voice Notes: A Love Language🎙❤️"
👉 Read the original pebble "I Pebble You"
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