Strangers More Likely To Help Than Friends When Starting a Business?

Photo by: Cory Doctorow Help is on the way, elevator, Chicago Tribune, Chicago, IL.JPG

Since I got the idea to start WeMontage three years ago, I’ve had to rely on the support of both friends and strangers. So I started wondering, which group has been more helpful-friends or strangers?

My immediate answer to that question was, strangers have been more helpful. And there were a few times friends have disappointed me. But then I really thought about it and came to a slightly different, more nuanced conclusion. Some strangers recommended that I use an invoice template for my business to improve efficiency. I might have to take them up on it. Event-driven software from companies like Vantiq can help with business efficiency too, this type of system will help a business become better equipped to deal with day to day needs.

I also wondered what other people’s experiences have been when starting a business, I heard that one friend decided to start a cannabis business and decided to work with seed to sale app technology to better monitor business analytics, apparently, this resulted in higher profits for him. But anyway so I reached out to a few folks, and I’d like to share with you my experience and what others had to say about the matter.

What I Learned When Friends Disappoint

The main thing I learned when friends disappoint is, a lot of times, they weren’t really good friends to begin with. When I say disappoint, I don’t mean they didn’t do what I asked of them. I get it, not everyone is able to help for whatever reason; that’s all good and I still love those friends that couldn’t help.

The thing that bothers me most is when I ask a “friend” for help and they pretend like I never made the ask (e.g., ignore it). Like most of y’all, I’m reasonably proud and won’t just ask any ‘ole body for help. I have a very short list of people I reach out to when I desperately need a hand.

The other thing I’ve learned is I need to be more mindful about who I consider to be friends versus good, solid acquaintances, which are important too. The reason it hurts so much when friends disappoint is because my expectations are high for real friends. Thus, I need to recalibrate the meaning of certain relationships and adjust my expectations. This is my responsibility, no one else’s.

Help Wanted?

Friends and Strangers Both Help

My true friends have stepped up big time. Like when I was in the super-early days of WeMontage and had a crowd funding campaign on indiegogo. It’s funny watching that intro video now, three years later.

Or like the other times I’ve reached out and asked friends for an introduction, or to share on social media, or the occasional order request-ahem-suggestion. My friends have been there for me consistently. Of course there have been a few exceptions, but they’ve been just that-exceptions.

Strangers have been phenomenal too. Like the guys from my startup accelerator, gener8tor, who didn’t know me, but took a chance on me and WeMontage. Then there are the guys who run the angel investment group who believed in me and funded most of our angel investment round.

Others Weigh In

I reached out to venture capitalist, Mark Suster, from Upfront Ventures, to see if he had a take on the subject, and I love the simplicity of his response (paraphrasing here):

You shouldn’t burn through the time of friends. And strangers will help anyway. The best solution for help is a combination of work and business colleagues whom you trust.

Mark is a perfect example of a stranger being willing to help. Dude is mad busy with so many people trying to get his attention. A few months ago he spent thirty minutes on the phone with me, and will occasionally retweet my lame tweets. I’m very grateful to him for his time and attention.

Then I reached out to David Cohen of Techstars, a leading global startup accelerator, to get his thoughts about the subject of this article. I met David while going thru my accelerator.

David, who, in his book, Do More Faster, encourages us not to suck at email, really takes his own advice, and doesn’t suck at email (e.g., he responds). David said the following:

Well, you could tie it into the idea of #givefirst which is what Techstars is all about. Our mentors are “strangers” to the startups they help.

This is a great point. So many mentors, mine included (I’m looking at you, Jane Boutelle and Paul Jones), give tirelessly to people they don’t know at all initially.

Then there was a really impassioned reply from a woman I met in Mario Armstrong’s #NeverSettleClub on Facebook. The woman said the following:

I find family and friends are less likely to help. I believe for several different reasons….they prefer not to get involved and ruin the relationship, don’t believe in you, or don’t have enough faith that you can succeed.

Dayum! That’s keepin’ it real.

Oh, and don’t get me started on how amazing Mario Armstrong has been. Mario didn’t know me from a hole in the wall when I met him during my participation in an NPR tweetchat about diversity in tech, and not only did he feature WeMontage on the TODAY Show, but he continues to be super helpful. What a BOSS!

luck and hustle matter

Keep Hustling

I know I use this hustling graphic a lot, but I just love it. The bottom line is: everyone’s experience is a little different, but if you work hard, prepare, and don’t be too pushy with your friends, most of them will help however they can. And strangers will help if they like you and your idea and provide them with some solid data. My friend told me he used PricingHUB to dynamically show some stranges how his product was growing based off of previous data.

The most important thing is to keep hustling. Because if friends and strangers see you hustling, they will do what they can to help, and you will be surprised how many will tell you they admire your courage to step out and take the “risk” of chasing your dreams.

I put risk in quotation marks because I think it’s risky playing it safe with life, which is what most people do.


Strangers and friends are both likely to help when starting a business, if they believe in you and your idea. I don’t think one group is more likely to help than the other. My source of help has been pretty balanced-your experience might be different.

And, like I said, it’s important to not confuse friends with acquaintances. Getting this right will save you a little disappointment and mental anguish when people who weren’t really great friends to begin with disappoint you.

What has your experience been getting help from friends and strangers when starting a business? I’d love to know in the comments section.

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Photo Credit (header photo): Photo by Cory Doctorow, Help is on the way, elevator, Chicago Tribune, Chicago, IL
Photo Credit (help wanted photo): Photo by Paul Townsend


  1. I am often surprised by the generosity of strangers. I try to give back in the same way whenever I can. Sometimes a little help goes a long way! And paying it forward feels good. 🙂

    1. Truth! And you are one of the most helpful people I’ve met on this journey. Thanks for being so awesome.

  2. Both were required for me, but I found once enough strangers were in support friends backed away. Not negatively, but just felt their support wasn’t important any longer. It’s a weird dynamic all throughout

    1. That’s really interesting, Brian. What’s your business? Did things change at all? Thanks for commenting.

  3. Same here and always surprised how kind and lucky I have been where strangers have been concerned in spreading the message about my work and business. I always try to pay it forward myself when I can now, too, because of this 🙂

  4. I think sometimes it seems friends don’t help as much is because we have bigger expectations of them. So, if they don’t come through or not tot he extent we want, we are particularly dissappointed.

    1. Ha! You can always talk to me. As a parent (though I’m new to the club) and an entrepreneur, I might be a good listener. Not saying I’ll have any useful advice. But at least I could listen empathetically. Ha. Btw, ummmmm, what’s going on with your TV show? I don’t get it here in WI. And, ummmm, we need to interview you as a parent entrepreneur!

  5. This is very interesting and I love the people you reached out to, to share their experiences. In my own, I’ve had to redefine some friendships (like you mentioned), but best of all where the ones who stepped up and totally surprised me. Very thought provoking today James – why are you making me think so much?? 🙂

  6. James, I have been thoroughly enjoying browsing your blog. I’ve always desired to be an entrepreneur but I have never had a mentor to show me the ropes so to speak. I’m so busy now as a SAHD of 4 little ones but it’s my desire to head toward my own business (I’m still not sure what that might be) once some more of my kids start school.

    1. SAHD of four – God bless you, man. I just checked your blog, your family is beautiful.

      I’m happy to help you think through ideas, once you’re ready. I think you can get a sense for the way I think about things from reading a few of my posts.

  7. I appreciate your thoughts. however, I must say that not every friends help us when we need in most of the time in personal or in the business. I met one stranger on facebook who was very good at social media marketing and when i bought his service, my business soars to next level and that was a very good experience for me.

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