The best $20 you’ll ever spend

If you want to start a business, the best $20 you’ll ever spend is to find successful entrepreneurs and take them out to lunch. They can be from your industry or other industries — it doesn’t matter. For example, if you’re interested in hospitality, you could pick up a hospitality magazine and see who’s doing interesting work. Then email them and ask to take them out to lunch.

Spend 90% of the time talking about them:

  • Ask them how they did it.
  • Ask them what mistakes they made along the way.
  • In the final few minutes, you can ask about your idea. Is it crazy? What should you be thinking about?

After you meet two or three people, you’ll start to see patterns that you hadn’t recognized before. And that’s when you realize how powerful it can be to ask others for advice.

Yes, advice is cheap: Most people love talking about themselves. But entrepreneurs have a curious fascination with helping other entrepreneurs succeed. (At PBwiki, a Silicon Valley collaboration startup I co-founded, a bunch of us spend time each week meeting with first-time entrepreneurs and helping them brainstorm…and this is a common thing in Silicon Valley.)

People want to help you. All it takes is you reaching out.

J.D.’s note: This is a powerful technique, and not just for entrepreneurs. Over the past year, I’ve had lunch with several people I admire, and always come away feeling inspired and filled with ideas. If you have the guts to ask, the rewards can be enormous.

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There are 41 comments to "The best $20 you’ll ever spend".

  1. Chett Daniel says 12 October 2008 at 05:37

    This post is absolutely true. I have a few people that I have met or have been friends with that have created their own business and have been very successful. When I pick their brain and ask them how they did it, what were they afraid of, what do they enjoy most, they openly discuss. One of these people said that is how he got to where he is, by asking those around him who were successful how they did it. Also I’m not opposed to contacting complete strangers. When I run across a website that has a good thing going, or I see a business in town I simply leave a message with the owner and let them know I am interested in what they do and how they do it and I haven’t been ignored yet. In general people like to talk about themselves, especially successful people. Do yourself a favor and soak it up. Oh I forgot to add, don’t bug them once they have shared. If they showed a true interest in helping you ask them if you can come back later for more advice once you get your project in the air. They will be more willing to help once they see you have used the advice they gave you the first time.

  2. Pierre says 12 October 2008 at 06:16

    Sounds like solid advice. My home university (University of Otago) has taken the initiative to set up such a program – acting as a intermediary link between local entrepreneurs and students wannabe entrepreneurs. The student pays for either coffee or lunch and the businessman/woman in turn reciprocates with his or her wisdom/experience/contacts.

  3. Nima says 12 October 2008 at 06:31

    This is definitely on top of my list for this week. I actually am taking a Entrepreneurship class in school where we have many speakers that I could contact.


  4. lilblueyes says 12 October 2008 at 06:43

    My (very wise) college Marketing professor had great advice along those lines (for those who can afford it!) … upon graduating, find the most successful person in the business you would like to enter into, and offer to work for them for free for a year. Then learn everything you can about the business from that person.

    Well how many folks can afford to work a year for free right out of college? Not this girl … but if I could have, it definitely would have been excellent advice, as I feel one’s first job/experience out of college can guide the rest of one’s career.

    I think the $20 lunch is a much more affordable (and practical) way to get the advice to jump start a business idea and/or career.

  5. InstaMotivation says 12 October 2008 at 06:59

    Great advice, I’ve done the same thing in the past. I work alone so I don’t really get a chance to socialize at work which is another benefit to this.

  6. Alison Wiley says 12 October 2008 at 07:06

    I sooo wish I had heard and taken Ramit’s good advice back in 1992, when I started my own company. Like many young people, I had more guts than sense back then, and my business and I ended up surviving a bankruptcy in the course of becoming wiser. I’d invite you to profit from my mistakes by looking at my top ten tips for entrepreneurs:

  7. Harold says 12 October 2008 at 07:44


  8. Writer's Coin says 12 October 2008 at 08:47

    JD and Ramit in one place: priceless.

  9. J.D. says 12 October 2008 at 09:20

    JD and Ramit in one place: priceless.

    Actually, this reminds me: When I was in San Francisco last spring, Ramit and I put this principle into practice when we met for dinner one night. We picked each other’s brains, just as he says to do in this post.

    • April Hope says 26 November 2019 at 18:31

      But who paid for dinner? 😉

      Fantastic post. Short, sweet, and damn helpful.

      Most people assume that highly successful people don’t have the time (or desire) to help others, but this post has given me the confidence to approach some of my idols.

  10. Emma Anne says 12 October 2008 at 09:30

    When I started my own law practice, I did this – took a guy who was successful out to lunch and listened to his war stories and advice. I also read an ancient book called something like “how to go out on your own right out of law school without starving.” I didn’t go out on my own *right* out of law school, but it was still mostly applicable.

    The best tip I remember is to keep overhead ruthlessly down, especially at first. Work at home or rent a single office in a complex, not right downtown. Don’t hire anyone permanent until you really need to. Make do with your current computer. You can afford a *lot* more bad months with practically no overhead.

  11. Susy says 12 October 2008 at 11:18

    This is so important. It is even better to develop long term relationships with people like this. We have a small circle of friends that have all started their own businesses in our industry and we get together often to talk about new ideas, vent frustration, encourage one another. This has been one of the best resources we could ever had. Worth much more than the $60,000 degree I have that I never use.

  12. Chris Holdheide says 12 October 2008 at 12:19

    This is a great way to build some creditalblity in your industry as well.

  13. Kevin says 12 October 2008 at 13:55

    First: credibility. Sorry, but the irony is killer.

    Next: Good post – there is no substitute for networking and learning from experts.

    Last: @Nima – spot on. Contact one of those speakers. As one who has addressed classes like yours, I can tell you it’s VERY rare to have anyone follow-up… and frankly I’d hire such a student, circumstances permitting.

    Good post.

  14. Jordan says 12 October 2008 at 13:55

    I agree picking successful peoples brains over lunch is awesome but if you’re a woman different rules apply.

  15. RenaissanceTrophyWife says 12 October 2008 at 14:14

    Good advice for life in general. Find the person you want to be in 20 years and learn as much as you can from them.

    Being a woman makes things slightly different, but you just have to adjust accordingly. Most of my role models have been men who didn’t have to worry about childbearing and rearing, while successful women in my field generally have a personal life (or lack thereof) that wouldn’t work for me. I think you can glean a lot from everyone, but realize that not every piece of advice is going to be applicable to your particular situation.

  16. Emily says 12 October 2008 at 15:36

    This is a wonderful idea, and something I’d never thought of before. It definitely sounds like a great way to get first-hand advice and network.

  17. Justin says 12 October 2008 at 15:51

    Another great thing about meeting people for lunch is that they can introduce you to other people they know. You might never have heard about this other person. This is the best kind of networking, because you’re not doing the hard sell.

    This happened to me recently. I meet with a mentor over lunch on a regular basis, and in talking about various things, it just so happens that he knows someone who used to be in a similar position to me. He offered to set up a meeting so we could talk, because he thought we might be able to learn something from one another.

    It’s unlikely that I would have discovered this third party on my own, and I’m really looking forward to seeing what I can learn from them.

  18. Eric Poulin says 12 October 2008 at 22:36

    You can get the same effect from joining (or creating as I did) a mastermind group, inviting people you consider successful to join. This way you get all those benefits and continued mentoring and feedback.

  19. Todd says 13 October 2008 at 06:37

    This is a good idea. Another way to do this is to set up a meeting with SCORE. You will get some good information and you can ask all the questions you want. Even go back for a follow up meeting. Best of all, it doesn’t cost you a thing.

  20. faithsalutes says 13 October 2008 at 11:47

    This is absolutely the best advice. I have traveled the world and been consistently employed because I have asked to “meet up” with people I admire.

  21. Caitlin says 13 October 2008 at 14:33

    $20? Where are you taking them? McDonald’s? Good advice but even if you don’t want to go somewhere flash, I think you’ll have to budget a bit more than $20 to pay for the both of you somewhere reasonable.

  22. WhitneyT says 13 October 2008 at 15:50

    I’d recommend asking people out to coffee. Everyone has 30 minutes to spare, even if they claim they’re too busy for lunch. Regardless of the meal, it shows initiative and ambition to cold call someone—great characteristics in new employees.

  23. Cheri says 13 October 2008 at 17:46

    This is such a simple thing to do that requires little investment on your part and has a huge ROI. It is even good to have more than one lunch with the same person. I have found that one lunch doesn’t allow you the time to get all your questions answered, so I try to schedule another lunch a few months down the road to talk again, if the first one went well. And just like you said, people like to talk about themselves and their successes, so scheduling another lunch usually isn’t a problem. Thanks for the great post.

  24. Lisa Winton says 26 October 2008 at 03:58

    Thank you, this was a great post; I came by way of Amy’s Humble Musings. We have found this same idea to be true in music. Our greatest help getting started came from other musicians who were further down the road than us, and all we did was ask for their advice, and they were so gracious to give it. Since I did all my asking by e-mail, I probably owe our friend a gift certificate for lunch out. ;o)

  25. says 03 November 2008 at 16:32

    Metorship… It’s one of the cornerstones of success – so true.

    The beauty of reaching out is that your mentors will have already been through some of the challenges you are about to face and so their advice can prove to be quite meaningful. Their input can save you time, money and even propel you forward faster than you could move on your own.


    Eff Jay

  26. Caleb says 22 December 2008 at 02:34

    I had my $20 dinner with my mentor.
    She say i should publish a book on saving money.

    I’m meeting sponsors and in dire need for content. the book may or may not make money. Is this article copyable?

  27. Kim: Blogging for Change says 19 May 2009 at 08:29

    Also presents a great opportunity for you to offer your lunch guest some free work (I learned this tactic during your recent visit to Denver!)

  28. Oleg Mokhov says 22 October 2009 at 09:41

    Hey Ramit,

    The most effective purchases are investments. The $20 lunch with someone who can help you achieve results is an investment.

    Just like buying a book for $10 that will accelerate your growth will give you a 1,000,000x return on investment, taking a value-giving person out to lunch is a huge ROI.

    The personal tips and direction you’ll get (as well as what NOT to do) is invaluable. Why try to guess? Just talk to somebody who’s doing what you’d want to do, and find out EXACTLY what to do. If it ain’t broke, don’t fix it.

    And what better way to talk to someone than over lunch? People love to eat.

    Great tip. Simple yet so effective,

  29. Caitlin says 26 October 2009 at 17:57

    No arguments with me about how taking people to lunch is a great idea. My only quibble is with the budget. $20? Is that for both of you? Even if it’s only for one of you, it’s a tight budget. You’re asking someone to give up their time – you don’t have to do fine dining but it shouldn’t be a sandwich either.

    • Peter says 11 January 2012 at 16:35

      You don’t necessarily need to be dining in New York either. $20 goes a lot further in Calcutta or Tallin, Estonia, if that’s where the lunch happens to be…

  30. Natalie says 04 November 2009 at 10:21

    Forget the dollar amount. Pick your own dollar amount. maybe Ramit is cheap 😉

    The dollar amount is besides the point!

  31. Siobhan says 22 June 2012 at 18:16

    Great article Ramit! I totally agree. So simple but VERY effective!

    One question – what if the person you want to connect with isn’t living in the same city or country. How do you recommend best connecting with them? Ask them to skype? Appreciate your feedback!

    Thanks 🙂

  32. Jen says 29 June 2012 at 05:27

    There are also free ways of meeting up with entrepreneurs (and other potential mentors)–using

  33. Michael says 04 September 2012 at 06:43

    This is really good advice. Thanks Ramit!

  34. Paul Colbert says 12 May 2013 at 15:41

    Ramit, very nice and fresh idea – spending an hour with someone who is already deep in the industry, sharing your ideas and views and asking for a feedback – the best investment of your time (and $20 is a small price). However, I am not sure that really valuable persons will be that easy to be invited for a lunch. In other words: YOU (personally, as a professional, etc.) should also be of value for them. In other case it will not work out (or even if it does, you will feel ashamed of wasting some person’s time).

  35. Gabriel Murillo says 03 June 2013 at 08:48

    I’ve been thinking about inviting my linkedin contacts to do this. Do you have any ideas on a good-short message to catch these people attention an invite to lunch without them thinking you want to sell them or pitch them something??

  36. TermLife2Go says 09 October 2013 at 12:00

    Another great question to ask is, if they were to do it all over again, what would they change and why.

    And always ask for a reference! I tend to end conversations with, “Who else would you recommend I speak to?” Sometimes you get shot down but the majority of the time you will get another name of another successful entrepreneur to have lunch with.

  37. marcus says 02 November 2013 at 12:53

    Wow, good article. It reminded me of when I met with this entrepreneur a year ago. He was kind enough to sit and chat with me at star bucks. I guess I was doing something right. But I never followed up on trying to meet other entrepreneurs. There are entrepreneurs that can help you with advice. Score is an organization that has entrepreneurs as mentors for startup businesses.

  38. Ulises says 03 September 2014 at 07:40

    Really inspiring, It reminds me of the book How to make friends and influence people. The power of listening and getting genuinely interested in the wisdom that others with more experience than us could provide.
    thank you I read Ramid’s blog and it’s nice to see him feature here!

  39. Aaron Davidson says 14 September 2015 at 17:26

    Thank you for the reminder. I read this post years ago and just came back to it. I have forgotten to take people out to lunch.

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