How to talk to your Entrepreneurial friends….

Jayne Moore
Jan 8, 2019 · 18 min read
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I’ve heard people liken the entrepreneurial path to “success” to a rollercoaster, but if that’s the case then this rollercoaster goes underground and into some hella dark tunnels, and it feels like there is a lot more time spent screaming in freefall or plunged into darkness than any ups and lofty views!

The ups are also way more fun than the downs.

So. Other than the fact that the ride might make you nauseous and doesn’t feel safe AT ALL, entrepreneurship is in fact nothing like a rollercoaster. And if it is then it is one that many many people have got on before you, but only 5% get off successfully at the end.

So… up for the ride?

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A song came on my Spotify this morning that is a firm favorite. It’s one of those songs that I feel oh so very deeply in that eyes closed and lyric belting kind of way. Every time this song pops up from my playlist, I hit repeat at least 4 times. I just neeeeed to hear it one more time.

The song is “Freedom” by Anthony Hamilton, from the Django Unchained soundtrack — and probably not what you were expecting me to say.

Now I am well aware of the context in which the song is written, I am well aware it is a brutal and unforgiving movie about slavery and the long long history of abuse and ownership, and that in this instance it is referring to a concept of “freedom” that I will never ever be able to fathom not having.

Disclaimer: I KNOW. I am well aware I am a white privileged female and even though I have enormous empathy and intellect to conceptualize another’s plight, I am still greatly aware that when it comes to that level of suffering, cruelty and entrapment, I will never ever know it. I got it and am not overlooking that fact. — Disclaimer over.

But humans are human and we live in our own realm of relevance and I am entitled to feel something on a personal level for this song.

So, in that very moment this morning, swaying in my living room to the raw and raspy tones of the lead Elayna Boynton, I felt as I always do, very “understood” by this song. And that’s one of the things that great music does, it makes you feel understood.

“Felt like the weight of the world was on my shoulders
Pressure to break or retreat at every turn
Facing the fear that the truth, I discovered
No telling how, all these will work out
But I’ve come to far to go back now

[Chorus: Elayna Boynton]
I am looking for freedom, looking for freedom
And to find it cost me everything I have
Well I am looking for freedom, looking for freedom
And to find it, may take everything I have

You get it.

I’ve been having a bit of a low period. All is fine, all is normal, I am quintessentially healthy and I am doing what I love. I am also balls deep in my second year of really “being in business”, and to be quite honest, everything is kind of hard. Everything is sticky. It’s all up hill. It sucks the strength out of you on a level you can’t really grasp until you are in it, and I am still aware that I am still only just getting started! Wheeeee

And here we begin with another story of an “entrepreneurs” journey of struggle — because you haven’t heard any of those yet have you?

So why am I writing this? Well, because I am a good writer… because I have quite a few friends in a similar position and I want to articulate this for them too, because it’s cathartic, and because it gave me an idea.…

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One of my best girlfriends is a Graphics Designer that has moved in to the art space and this is really really “ her thing”! It came out of nowhere, it was a sharp and sudden pivot, and overnight it brought her to life with creativity, inspiration and PASSION!

And she is going for it hard! She is burning for it from within, she is fearless and hungry.

Like literally hungry.

And fearless in the only way you know how to be when you are absolutely petrified.

Petrified of failure, petrified of the expense, petrified of it not working, petrified of next months rent, petrified of your patient partners patience wearing thin, petrified of having to explain — yet again — to your parents what exactly it is you are doing and how that affords you a living, or how it might actually not for a while…, petrified of the life you may be sabotaging for your unborn children and absolutely petrified that the dull ache on the left side of your jaw is not in fact a wedged popcorn kernel, but something far more severe that may require emergency dental — for which you are not insured for.

The fear of writing a press release and sending it to every magazine editor who’s email you can guess becomes a little less scary in the face of all the rest.

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Her and I talk a lot, as we are those rare beings that “get it” and share that insider right of passage that is trying to make something you love to do pay for itself. And then for you.

Another one of my femme fatal entrepreneurs is a few years ahead of me in business, she has always been someone I look up to, and is a lifeline of very smart and very funny insights, with a sarcastic and ironic humor that often feels like oxygen.

She has been written up by all the big mags, Vogue, Elle, O mag, and is adored by some pretty solid celebs of influence — Lauren Conrad and Blake Lively to name a few — who have posted about her and name dropped her brand a few times, AND she is a regular product du jour for a whole host of bloggers and heavyweight instagrammers, making her a darling of her niche.

We share a lot in common — past careers, lives lived and loves lost, moral and ethical principles, oh, and merciless and unrelenting debt. We would both be a lot richer if we didn’t have businesses and/or cared less about ethics and the environment. True story. Fortunately we have the ability to make each other pee with laughter whilst sharing our dirty little secrets and interest rates, and reassure each other that this really does all get better at some point in the near future, all over cheap wine and french fries.

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Thank fudge I have some really pretty remarkable friends doing this too, because one thing no one really explains to you going in, is how starting a business might cost you your friendships — and not because you have shitty friends (I mean you might, but bye to that!), and not because you are a bad friend yourself, but because it gets increasingly harder and harder to be “normal”.

Your own self esteem is going to take a pounding, your financial situation will be rocked and your days are going to be an unpredictable clusterfudge of simply getting by, completely unguided, and it becomes exceedingly difficult to be utterly honest, upbeat and fun, especially whilst watching your friends order another bottle and “things to share” that you’ll be expected to split the bill for. And it takes near super human strength to hear that Chrissie’s nanny bought the non organic Almond milk for the second week in a row…. and not completely loose your shit.

Or, as in my case, become really really quiet and say less and less. That’s also known as English rage.

Truth of the matter is I don’t really want to go out anymore, not because I’m sad or depressed but because there is so much I am aching to do! Time is so precious and my list is so long! And that’s not woe is me, I am not being impressive, in fact the list is so long because I’m really NOT impressive, but THIS is entrepreneurship! I am absolutely aching with urgency to get on with things and just move the needle incrementally forward!

It’s not you, it’s me.

I don’t have small talk in me right now, I don’t care for gossip, I’m not feeling all that silly and light hearted, I truly don’t mean to be a snob but I don’t want to have to explain what I am learning and trying to do and I don’t have it in me to paint a pretty picture when you ask “how’s the business” or make comparable references to some hotshot example that has made it. I’m not bitter, at all actually — the “How I Built this” podcast is my guilty pleasure and an absolute source of strength — but I’m just “IN IT” right now and your questions might make me cry. Or scream.

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My brother and his wife had several miscarriages and it ultimately took 4 and a half years — and several rounds of IVF — to conceive and carry their first child to full term. It was a rough ride. She was quiet and distanced and seemed to fade away in front of us. He was a strong and supportive rock, but looked as if he needed a good cry, and their pain leaked out in all sorts of ways.

People ask the most wildly insensitive things — well meaning and simply not knowing — and those that do know, simply don’t ask at all.

There was more elephant than there was room, and with every miscarriage, the elephant invited a friend.

This was a really hard, long and dark period for my brother and his wife, but it was also pretty hard on those that loved them to know how to be there, what to say, and what not to say.

I was very close to them during all this, and at some point my brother produced a pamphlet, a flyer of sorts, on how to support and talk to anyone going through a miscarriage, as he wondered if I might share it with the family. This thing, this simple piece of paper, was BRILLIANT! It was so eye opening and understanding. It made a huge impact and I wish I still had it.

Second disclaimer. I am not making light of the situation, so even though there is a lot of humor and banter in my language, please don’t feel like I am dismissing what my brother and his wife were going through (and I am delighted to report they now have FOUR gorgeous healthy children, and the elephants quickly left when they realized there were more children than there were rooms!) but life moves on and my brother’s unit is happy, and I think there is something to learn and share from the intimacy of heartache. Disclaimer over.

So, inspired by this and on talking to my hustling beat up friends, I decided to put together my own pamphlet of sorts, on how to talk to your entrepreneurial friends!

So here goes:

How to talk to an entrepreneur.

— A chatty guideline on how to communicate with your distressed and broke, overly caffeinated entrepreneurial friends.

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Just because they create their own hours, do not assume they are free on yours.

Yes, technically we work for ourselves, in our own time, and possibly from home… but you have to understand that the amount of work to get done, in order to even make a dent in the to do list and stand a chance of ever being heard of out there in the universe, we are probably multi-tasking, in roles we aint qualified for, overwhelmed and working 16+ hour days and eight days a week. Yes. I said eight.

Yeah, technically could I stop for lunch, or am free for a movie, and yes, it’s true, we need to be pulled away sometimes, but more often than not they just need to lock down and crack on, for like four years, and know that you love them anyway, and know that YOU know that they love you.

No guilt trips or pouting welcome.

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Do not suggest a part time job

Ok. It’s not unreasonable, but nor is it something that will not have occurred to them. Money matters and money talks, and never more so than when you are in business. But the reality is they will either

a) be doubling up and working all the hours they have got already — hard hard hard.

b) already have some sort of part time gig that just gets em by and be working all the others spare — the best case scenario and also, very hard.

c) Have gone all in, balls to the walls, and over stepped every single financial boundary they said they never would, and are acutely aware of every penny spent. They will know when it’s time to wave a white flag and get another side hustle. You suggesting it will only ever be a kick to the balls when a wo/man is down.

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Do not suggest a new career entirely

Read the above, and then triple it. Unless you have a really great idea/ opportunity/ easy win of a ground breaking suggestion, based on their strengths and glaringly brilliant abilities, do not suggest ‘em doing something else…. or someone’s getting hurt and my money is on it being you. WE KNOW! Truly. We know just how hard our back is pushed against the wall (and sometimes it takes this!) and entrepreneurs have a different breaking point to the rest the world, a different timeline and a different idea of success. The suffering is worth it, with the end goal in sight. Please let them be the decider of their fate.

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Do not suggest Nobu for dinner, and if you do, accept them not coming.

I’m a New Yorker, I have fancy friends that worked their ass up the system and have big titles and healthy paychecks. I also have friends that married men with big titles and healthy paychecks. Some of my friends have cabins upstate, Hamptons homes and rocks on their fingers as expensive as the down payment on both. And I love them! They are awesome. But my overworked amex is not nearly as heavy, metallic or shiny as theirs, and when it comes to their high life, sometimes I just can’t hang. That’s not a knock, not a snub, I don’t feel lesser than you nor do I wade in my hard working self righteousness, I quite simply can’t keep up with the Joneses, and am cool with that…. if you are! Invite your entrepreneurial friend to a westville or a cheeky pad thai at your local, cuz we are DTF! (down to feast you filthy buggers) but have a whole different perspective of the mighty dollar.

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Do not ask where the money has come from.

K, so this ones a good one, but a weird one…. Just don’t do it and here’s why:

  1. They have used all their savings, passed their own self set limits several times and have sunk into the depths of debt which is TERRIFYING. They will one day take pride in being self financed but right now, probably cant breathe.
  2. They have investors. Yay for them, sounds really cool, but this is like the same situation as above, but with OTHER PEOPLES MONEY, and — for me at least — that would feel even scarier. Add to that that most entrepreneurs in their first round get it from the three F’s — Friends, Family and Fools — they are going to be more than aware, at every event, behind every message, on every post they post, and that every conversation of “how is the business going” is laced with a whispered “how is my money doing”. Even if it’s not, it will feel like it is.
  3. They have a sugar daddy/mammy of sorts, either parental, betrothed or sponsored, and this in it’s own way is uncomfortable. They will feel a little sticky perhaps telling you of their persuits, or a little less authentic in the struggle somehow, and there is enough stick and imposter syndrome in going it alone to sink a very large ship. At the end of the day, who cares, mind your own, good on em for using any cushy backing for a passion and purpose, when a spa and pedi would be so much easier.

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Do not be offended that they don’t partake in your baby shower or house warming party

K, this is a tough one. Because you ARE important and worth celebrating, as is your big day and your bundle of joy, AND all the MILLION events around it.

But there is sort of a common window where people do certain things, namely: start businesses, get married and have kids. And in my own personal circles and observations, more often than not, they are doing the former, or the latters…. Which means at the same time as your brave entrepreneurial friend is sliding down the ladder, scrapping their security, slashing their income and spending all their savings, you are doing big, glorious and lets be honest, expensive things.

In one year I had six weddings, all close friends, and FOUR of them were abroad, four of them had several gift baring events — engagement parties, bachelorette parties, bridal showers and the event itself — as well as four airfares, the hotels, and the meals out.

I made five out of the six weddings, and had to let the bride of the sixth know — too late in the game — that I couldn’t go. It was horrible. And I felt horrible, and retched and embarrassed and guilty. That’s a lot to feel about celebrating someone ELSES decision and celebrations. I get it often from my friends back home “When are you coming home?/ we never see you/ can you make a bday/ baby shower/ christening…” but you must please understand that everything we are doing, we are probably doing alone, carefully financed, and it all goes completely uncelebrated.

(I am going to make another blog about us throwing “I started a business” parties, and having several gift baring events around it, but right now that’s not the reality.)

I am in my mid thirties. I know I won’t get married, if at all, until I am probably in my forties, and I have shelved even thinking about children for another 3–5 years. That’s my decision because I so want to stand on something of my own, that I have built, and don’t want to have a wedding until I can afford it, nor children until I can give them a life that I want to.

But the same way you might save for your wedding, and therefore choose not to do certain things, please accept that your hustler friends may have to opt out from your baby shower or one year olds birthday. Please forgive them this, and support them with understanding and “room”. We all make different choices and mine aren’t made to judge yours, so I ask of you the same, and extend it to the hustlers that you know.

So, the good stuff, what to do?

Well this is easy and fun!!!


Ask. If you mean it…

Yes ask how it’s going, if you can really take the time to listen and really care about the answer. It’s ok not to, but if you can ask and listen without fitting it in to your frame of understanding, you will be gifting your friend a lifeline, and a “tissue box” for the tears we have learned to cry on the inside.

And do this on the one on one, at a bar or on a walk or over coffee, when others won’t be on the listen in.

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Get excited!

Get charged up and jazzed for your crazy mofo friend!! They are doing something nuts, and nuts is extraordinary!! It might not be smart and you might not think it’s a good idea, but you know what, they are brave in their madness and that in itself is worth celebrating and supporting. Some of the greatest leaders, change makers and inventors of our time were absolutely stark raving out of their mind, and even if your friend is not reinventing the wheel or healing cancer, they are doing something enormous for themselves, so get behind em and cheer! Running a marathon is also a really crazy idea, but peeps turn out in the thousands to cheer, and it is a wonderful and inspiring day!

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Ask how you can help

Chances are you might not be able to, but just asking will help them feel less alone. Sometimes that might look like lending your expertise at spreadsheets or helping them budget. Sometimes it might be physical and you spend the day in a wood shop sanding toys or arranging shipping materials in to a logical and tidy set up. Stepping in to their world for a day will actually be fun, as will the warm fuzzy feeling you get at the end. Maybe you can’t do a damned thing, but they will appreciate you asking.

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Celebrate the small stuff

Ask about the details, the milestones and achievements, because there is a good chance your hustler friend didn’t stop to notice them, didn’t think to mention them, and certainly never took the time to celebrate. We wont get excited for the small wins because we are going for the big, so you have to do so for us!

Beat it out of them and go bananas! Bring coffee and sketch something cute on the lid, bring a balloon to your cheap-o-dinner, order a cocktail and have it waiting for them, and send nerdy inspiring cards, silly GIFs are also so so welcome, I can pee myself laughing at the timely delivery of an appropriate GIF. These are the lifelines that keep me going, and I will never ever forget the friends that gave them.

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Shop, stupid!

A good entrepreneur will shove stuff in your face and make you.

A good friend won’t.

If your friend has a business, that you can afford to buy in to, in anyway, no matter how small, please do it. For the first year my people really forgot I made jewelry, and I would never dream of emailing my friends promo stuff! But with each friend that came to me with an order, a custom idea, a custom “can you do” or shopped online, or told a hubby to shop online… I got a little stronger, a little boost, both financially and emotionally. My website process got a little smoother, my order fulfilling a little slicker, my production a little more seamless, my time management a little tighter and more efficient.

With every single supporting sale I got better — and that’s one of the greatest gifts you as a friend can give.

— — — — — —


We are an interconnected species now! I once heard the amazing Tiffany Dufu talk, and she really struck me with something she said. She was talking about her niece’s endeavor in to journalism and her niece had said “I want my writing to speak for itself”, and Dufu replied “Honey, it won’t…” she went on to explain that no matter how good you are, in this day and age, your work will never speak for itself as nothing a single person can produce can shout louder than all the noise the rest of the world — and those far less talented — are already making. You have to enroll your friends and family in what you are doing, and let them know your triumphs and successes, and get THEM honking the horn for you.

So this is you dear reader… this is your role. Honk your entrepreneurial friends horn, wherever you can, on your social, via emails and in person. Get proud of them and market for them. The louder you honk, the more chance you stand of getting a baby shower gift too!

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Pour wine. Serve food. Believe in them.

I walked in to my best friends apartment about six weeks before Christmas, I was late, I had gotten engrossed in a task and was pretty beat. I walked in, put a bag of groceries on the floor, and she said “Hey! How’s it going” and I burst in to tears. I’m english and really don’t cry much, so this was for me bonkers behavior, but she didn’t flinch, she nodded in a “got it!” kinda way and said “lets get some wine” and proceeded to open a nice Italian red.

I recovered, said nothing was more wrong than usual and set about chopping veg for dinner. It was all I needed, her to be ok with the fact that sometimes I wasn’t ok, to not be uncomfortable with it, and to pour me a glass of wine.

She took a photo of me stirring the pot, in my beat up harem pants and sad sorry expression, wine clutched in my hand, and smiled with absolute conviction. “I can’t wait to show you all these pictures one day, when things are going great and you are a household name and have forgotten all this shit” and she meant it. Even when I don’t believe it, she, and about four significant others, really utterly truly believe in me.

Be that for your ballsy bulldozed friend. Wade in on their no’s, interrupt their friday nights working, notice when they are silent on the group chat, poke them just enough to make them open up, and maybe cry, and then tell them, with absolute conviction, it’s going to be ok and you believe in them.

And pour some more wine.

I promise you, it will buy you a spot in entrepreneurial heaven.

Over and out, JM xxx

Jayne Moore

Written by

New York based writer with a distinct British undertone, an observer of life, love, loss & perspective. In love with the details & idiosyncrasies that make us.

Jayne Moore

Written by

New York based writer with a distinct British undertone, an observer of life, love, loss & perspective. In love with the details & idiosyncrasies that make us.

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