Squibb: Ask for Advice, Not Money

beginner5 min read · updated 2026-06-20

As taught by Simon Squibb · source

Squibb: Ask for Advice, Not Money

The lesson, in plain terms

Simon Squibb — the homeless-teen-to-millionaire founder of HelpBnk, with 22000000 followers across his platforms — has a counterintuitive rule for anyone who needs capital: don't lead with the ask for money. Lead with the ask for advice.

His exact framing, given to Sage Advice: "Do not ask people for money because they'll give you advice, but if you ask people for advice and they like what you're doing, they'll give you money." The move is not a trick. It is a reversal of what most first-time founders do, and it changes the entire shape of the conversation.

When you walk in and say "I need $50k," you have framed the person across the table as a wallet. Their instinct is to protect the wallet. They put up defenses, poke holes, and hand you a polite list of reasons it won't work — i.e., advice — and you leave with nothing. When you walk in and say "I respect what you've built; can I get your read on this problem?" you have framed them as a mentor. Now they are pulling the idea apart with you, not against you. They get invested in the outcome before they are invested in dollars. And the people who give you the best advice are exactly the people best positioned to write a check.

This is not new wisdom dressed up as Squibb's — it is an old adage he sharpened for the social-media era. The saying "ask for money and you get advice; ask for advice and you get money" was in print as far back as 1975, common in nonprofit fundraising circles for decades. Squibb's contribution is making it a daily, practical operating system for ordinary people starting businesses.

Why it works (the mechanics)

Three things happen when you ask for advice instead of money:

• You lower the stakes, so people actually engage. Money is a yes/no with real downside. Advice is free for them to give and flattering to be asked for. You get the meeting you would never have gotten with a cold funding pitch.
• You trigger ownership. People support what they help build. Once someone has shaped your plan with their own ideas, they have a stake in seeing it work — the same psychological pull behind why founder-investor relationships are described as a long-term commitment, not a transaction. Stripe's own founder guidance echoes this: treat the conversation as relationship-building, not a single ask.
• You learn whether the money is even worth taking. Advice surfaces who actually understands your space. A great advisor who later invests brings connections and credibility, not just cash. A bad one shows you their thinking is shallow before you are tied to them for years.

Founders who do this well report the same pattern that angel investors describe: don't ask for money first — use the conversation to get advice, sharpen the pitch, and let the funding question come up naturally once the person is already pulling for you (per Technical.ly's investor panel).

How to apply it

• Make a list of the 10 people you'd want money from — then cross out the word "money." Reframe each as "people whose brain I want for 20 minutes."
• Open with respect and a specific question, not your deck. "You scaled X to Y. I'm stuck on [precise problem]. What would you do?" Specificity proves you did your homework and respects their time.
• Actually take the advice — visibly. Go do something with it and report back. "You told me to talk to my first 10 customers. I did. Here's what I found." This loop is what converts an advisor into a backer.
• Let them raise money first whenever possible. If the advice has been good and the progress is real, a natural "how are you funding this?" will come. That is when the ask lands — they're already on your side.
• Know the one exception. Squibb is explicit: in a formal pitch built for investment — a Dragon's Den / Shark Tank-style room, a demo day, a pitch event — state your number plainly. The advice-first move is for relationships and cold approaches, not for rooms where everyone already showed up to talk money.
• Run it on more than capital. The same reversal opens doors for hires, partnerships, and press. Ask a great operator for career advice before you ask them to join. Ask a journalist what makes a story before you pitch yours.

The Black Label takeaway

Money-askers get doors closed; advice-seekers get mentors, networks, and — eventually — the money too. The asset you're really building in an early conversation is not a check, it's a relationship with someone who now wants you to win. Lead with the question, do the work they suggest, come back with proof. The capital follows the relationship, not the other way around.

Lesson distilled in our own words and applied to operating practice. Original concept and modern framing: Simon Squibb (simonsquibb.com).