Entrepreneur sending a cold email to connect with successful founders
Entrepreneurship

How to get advice from very successful people

Learn how founders can network with successful entrepreneurs, write better cold emails, and build meaningful relationships that open new opportunities.
Aloke Pillai, product designer at Pastel
Aloke Pillai

Very successful people are busy, but you can get their attention in a few ways:

  1. Helping them with grow and improve (e.g. expanding their audience, giving them feedback on their projects)
  2. Doing great work yourself and building a personal brand that attracts their attention organically.
  3. Doing something creative and personal to get in front of them, with persistence and without being annoying (it’s a fine line…)

My personal experience has been focusing on that last method via...

Cold emails

For over a decade, cold emails and luck are the two factors that've led me to many unique opportunities like internships at fast growing startups in Silicon Valley, building a highly profitable freelancing career, meeting incredibly talented individuals to start companies with and my favorite, getting to work with Kanye West.

When we started working on Pastel, I made it a habit to reach out to very successful individuals that had faced similar problems to what Pastel was going through at early stages. It helped me find a different perspective. Building relationships with experienced founders is also one of the best ways to accelerate learning new skills throughout your career. I’ll outline how I go about doing this.

I’ve found that successful people really respect two things: consistency in your work and following through on what you said you would do. Being aware of this makes your messaging even more potent.

Let’s say I want to email the CEO of a company I admire.

First, I would find out what this person values. What do you find inspiring about this person? Was it their story or how relentlessness they are? The key is to find something remarkable that, any mention of it, would make them think: “Wow, this person noticed."

If you’re contacting a person who you noticed is very detail oriented, mention that. It makes a difference.

Second, try to understand the state of mind of the person when they open your email. They may see hundreds of emails that very day and want to use their time more wisely. If they are willing to help, they want to help people who deserve it.

The structure of the emails I use follow this model loosely:

  1. Mention why this person is remarkable to you.. but keep it short! 1-2 sentences
  2. Set the scene for the problem you may be facing and ask a simple specific question. For example, if the person serves the same type of customers as your business, then you may want to ask how they went about creating relationships at scale with that audience in the early days. 1 sentence
  3. Let your email signature explain what you do at what company. Bonus points if your job and company can be explained with 3-4 words in your email signature.

And then you press send. Now what?

You may be tempted to start checking if the person opened the email or to keep refreshing your inbox. Here is a trick: if you really admire this person, you wouldn’t mind working on building this relationship over months, or years. Taking on this mindset helped me think long term about relationships in general.

If you got your reply:

Great! keep building rapport, trying out their ideas and possibly even getting them on a call to talk further.

Many successful entrepreneurs credit strong relationships and consistent execution as key factors in building a successful agency.

If you don't get your reply:

Get back to work and execute relentlessly for 3-4 months. After you have your snippet of experiments, successes and failures, ping them back with a short email:

  1. Mention the progress made and what you learned. 1-2 sentences
  2. Set the scene for a new problem and ask another specific question.

Adopting this kind of mentality of working on long term relationships gives you an incredible head start to building out your network.

The strongest professional networks often create opportunities far beyond your first business, including investing in other entrepreneurs.

If you would like to try this out, I’d suggest creating a list of 10 people in your field you admire and put those names in a spreadsheet with a list of questions you may want to ask them. Send them a short note and keep them updated with your progress every 3-4 months.

This habit signals a few things: you are in it for the long term, you are a doer and you ask smart questions.

Whether you're building a startup, agency, or product business, Pastel helps teams collaborate more effectively with clients and stakeholders.

Also, If you have any specific questions, feel free to contact me at aloke@usepastel.com

FAQ

What's an effective way to get a busy, successful person's attention?

Three approaches tend to work:
- Helping them grow, such as expanding their audience or giving useful feedback on their projects;
- Doing great work yourself and building a personal brand that draws attention organically;
- Reaching out in a creative, personal way with persistence, without tipping into being annoying.

How can I network effectively with busy or successful people?

Focus on one of the three approaches that consistently work: offering to help them grow, building visible credibility through your own work, or a genuine, persistent, low-pressure outreach. Cold emails paired with persistence are what have worked best over a decade of trying.

What's the best way to build a professional connection with someone I admire?

Before reaching out, find out what that person actually values, whether it's their story, their work ethic, or something specific about how they operate, and mention it directly. Noticing something real and specific about them is what makes someone think you deserve their attention.

How do I get good advice from someone successful?

Ask one clear, specific question tied to a real problem you're actually facing, rather than a vague request like "can I pick your brain." Busy people are more willing to help when they can tell the question is thoughtful and the person asking is serious.

What traits do successful people value most in someone reaching out to them?

Two things in particular: consistency in your work and following through on what you said you would do. Keeping that in mind makes your outreach messaging noticeably more effective.

What should the structure of a cold outreach email look like?

Mention something specific and genuine you noticed about the person, ask one clear and specific question tied to a real problem, and keep the whole message short, since the person may be opening it among hundreds of other emails that day.

How can I meet my heroes or people I look up to in my field?

Cold emails combined with persistence are the most reliable path. Over a decade, that combination led to opportunities like startup internships, a freelancing career, meeting future co-founders, and even working with well-known public figures.

How do I find a mentor if I don't already know one?

Build a list of about 10 people in your field you admire, keep it in a spreadsheet along with the questions you'd want to ask each of them, and send each person a short, genuine note to start the relationship.

How do I build a genuine connection with someone I've just met professionally?

Treat it as a long-term relationship rather than a single ask. Update them on your progress every few months so they see you're serious, consistent, and following through, which is what earns real trust over time.

What should I do if I never hear back after emailing someone I admire?

Keep working. Execute relentlessly for three to four months, then follow up with a short email mentioning your progress and what you learned in a sentence or two, followed by a new, specific question tied to a new problem.

What kind of advice should I ask a successful entrepreneur for?

A specific question tied to a real, current problem you're working through, not a generic one. Specific questions are easier for a busy person to answer well and signal that you've already put in real effort.

Is it okay to keep reaching out to someone successful after the first message?

Yes, as long as it's persistent without becoming annoying. Sending a short update every three to four months, focused on real progress and a new specific question, signals you're in it for the long term rather than looking for a one-time favor.

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