Site icon Magpie by Jen Shoop

On Entrepreneurship.

Hi loves.  I’ve missed you.  I’ve missed blogging this past week.  I was frustratingly called for jury duty and then selected to serve on a jury, which left me very little time to stay on top of business*, let alone carve out time to blog.

*I mentioned at some point that I founded a technology business about six months ago.  Things are going really well (customers! growth! yes!) and I have been contemplating sharing some of that journey at some point.  It has been a labor of love.  I don’t think I’ve ever done anything more difficult in my life.  I used to read articles/books by entrepreneurs who warned me of this and I’d think to myself, “OK, but whyyy.  Tell me why it’s so difficult!” And they’d say vague things like: “Getting to product-market fit,” “facing constant rejection,” “being forced to make decisions every day that may change the trajectory of your business forever,” and I’d think, “Eh, that doesn’t sound that bad.  I think I could do that.  It’s tough to be an employee, too!  It’s tough to deal with the inter-office dynamics and be beholden to a boss who you may or may not agree with (and, in some cases, who you may not even respect!)!  So how can it be that much more difficult?”

Well, Magpies, I’m here to tell you three cold hard truths about entrepreneurship that have made the last few months incredibly challenging:

  1.  You are broke.  For, like, a long time.  Every penny we make, we put into our business.  Every dollar of investment we receive, we put into our business.  This means living off of savings and cutting way back on expenses so that we can personally afford to continue the business.  I’ve only learned after the fact that most entrepreneurs don’t even take a salary for the first few years of starting a business–and even then, they’ll take a small one.  One of the sharpest female founders I know just told me the other day that she’s taking a salary of $35K even several years into her business and even while she’s paying her employees market rate ($80, $90K).  Of course, the pay off, if things work out, is worth it.  And that’s what entrepreneurship is: taking on insane risk and betting big.  But it’s tough and stressful and sometimes I want to punch a wall.  I tell myself this makes me hungrier and more angsty — all of which will leads me to hustle even harder.  But — it really sucks.
  2. People constantly tell you you’re wrong and that you won’t succeed.  Mr. Magpie calls this “the shit pile.”  Excuse my language.  But it’s true.  He told me once that being an entrepreneur is just like constantly trying to dig your way out of a big pile of crap people are throwing on top of you all the time.  I didn’t believe this at first.  I thought: “but how can people be mean like that?” and “well, no one will actually tell me that to my face” and “I’ll be so good at what I’m doing no one will dare tell me otherwise.”  Ha ha ha ha ha.  One of my early conversations about my business was with a very well-respected professor who was head of entrepreneurship at her elite business school.  We’d crossed paths a bunch of times and I thought it’d be helpful to get her perspective and possibly get access to her connections.  In the course of a 15 minute call, she told me I didn’t have the background or expertise to be doing what I was doing and that “it was going to be very tough” for me to succeed.  It hurt, but I didn’t take it lying down.  It lit a major fire under me.  It also taught me an important tactic in any kind of sale or negotiation: if the conversation is going haywire, take control of the situation and bow out.  A very seasoned sales advisor told me the same thing a few months later: “If at any point you feel uncomfortable, shut it down with a polite: ‘I can tell this isn’t going anywhere, so let’s end the conversation here.'”  I’ve learned to develop a thicker skin and to shut down conversations if they aren’t going to be productive.  And, of course, there’s a difference between constructive criticism and the shit pile.  I spend a good portion of each week talking to advisors and experts and entrepreneurs who are much smarter than I am and who help me understand where I need to be changing my approach.  Sometimes this is hard to hear, but I am eager to learn and grow and so I’ll take it.  But if someone is being negative just to be negative?  Or to seem cool or like they know more?  Um, no thank you.  Shut.it.down.  A very smart entrepreneur here in Chicago recently told me: “Pessimism always looks cooler than optimism.”  Aka, it’s easy and cool to be negative about things.  Much harder and less popular to have the conviction in being successful.  But guys, even with a thick skin and a gritty determination to succeed, it is really frustrating and demoralizing to be constantly told that you won’t succeed, or that your idea isn’t good enough, or that you aren’t good enough.  Despite the fact that I think I’ve gotten better about redirecting conversations or ending them altogether or at least brushing them off, I’m still occasionally sandbagged by words of negativity or doubt.
  3. You are constantly failing.  We are in intense learning mode right now, constantly tweaking and adjusting our product, our marketing, and our market segmentation (all fancy ways of saying: what we’re selling, how we’re communicating what we’re selling, and who we are selling to).  Because we’re adapting as quickly as we can, we’re constantly forming and testing new hypotheses, and often disproving our own best guesses.  AKA, we’re always failing.  And that can be kind of a downer.  In these moments, I try to channel one of my favorite quotes from Thomas Edison: “I haven’t failed.  I’ve just found 1,000 ways that won’t work.”

And then here are three beautiful facts of entrepreneurship:

  1.  You make all the decisions.  You and you alone.  It is freeing and terrifying and addicting at once.  You don’t need to ask for permission for anything.  You can decide you need to fly to New York for a meeting tomorrow and do it.  You can decide to change the language on your marketing materials and do it.  You can choose to hire someone, or to have a meeting with an investor, or to reach out to customers, and you can decide how and when to do those things and why to do those things and what you want out of those things.  You totally control your day, your week, your life, your success.  All of those exhausting dynamics you used to have with your boss and colleagues are gone.  It’s all about you, what you think, and what you do next.
  2. You become much smarter than you ever thought you were.  I have never learned more in my life in such a short period of time.  I feel like I crammed four MBAs into the span of 6 months.  I’ve had crash courses in marketing, sales, fundraising, and the basics of setting up a legal business–I’ve made thousands of mistakes and learned from them very quickly.  I feel fortunate that I’d already learned how to vision and manage technical products, lead technical teams, and manage at the executive level–because I already had a big leg up in those areas.  But everywhere else, I’ve been just like a sponge soaking up as much advice and inspiration as I can, whether from advisors, workshops, online courses, articles, or books.  And even though this means that in some ways I constantly feel like I know nothing, when I look back over the last six months, I’m astounded at how much I’ve learned.  I was just chatting with a fellow entrepreneur the other day — she was preparing to hire her first engineer and showed me her job description and talked through her expectations.  I was astounded by how much concrete input I had for her based on my experience having hired an engineer myself.  Something similar happened a week later when another female founder told me about a problem she was having with sales.  I was shocked at how much I had to say on the topic.  For someone who prizes learning above all else, these were big moments that signaled how much I’ve grown in the last six months.
  3. You are solving a problem you care about. I would not be building the business I’m building if I did not think there was a huge problem to solve.  Every day, I have the beautiful job of talking to customers who love what I’m working on and love what we’re building.  They love that we’ve solved a painpoint for them.

I have so, so, so, so, so much for more where this has come from.  I could spend literally a full day talking about what I’ve learned from sales.  Maybe two full days.  Maybe a full week.  It’s ROUGH being in the trenches!  I also have a lot of thoughts on product design that I’ve learned through the school of hard knocks.  And on hiring.  And on being a female founder.  And on a whole host of other topics.  But I don’t know if that’s what you little Magpies are interested in, so I’ll keep it to this high level for now and maybe share some additional thoughts down the road if you chicpeas want some more of this.

To conclude, though, I’ll share what you all probably came here for: some shopping/fashion inspiration.  So I’m going to share a handful of things I absolutely couldn’t live without during my last six months as an entrepreneur:

+A sturdy workbag.  I am constantly lugging my laptop, notebook, calendar, phone, cords, and “emergency kit” (more on this later) everywhere I go and I just can’t cut corners here.  I’ve stuck with my Louis Vuitton Neverfull or my Cuyana tote most of the time.  I’m now contemplating refreshing the look with either a Goyard tote or this reversible Gucci ($1,250).

+An emergency kit.  I am often on the go from 7 AM in the morning until 7 PM at night, and I never know what the day is going to throw at me or how much time I’ll have in between meetings to run into a CVS.  So I keep a well stocked little emergency skit in one of my monogrammed Cuyana pouches ($110 for set of 2), and it consists of hand sanitizer, Advil, bandaids, Tums, tampons, gum, extra pens, safety pins, a stain remover stick, a nail file, and usually some sort of emergency snack/granola bar.  I can’t tell you how often each of these items has saved the day.

+Amazon Prime.  I order my whole life on Amazon.  Like, literally, it has been my savior.  Whether it’s stocking my house for guests that are visiting over the weekend when I won’t have time to pick up candles or cocktail napkins to make myself look like a good hostess, or snagging cosmetics like make up wipes (this stuff is awesome), or — perhaps more importantly — fueling my book list (I just finished, and loved, this).

+Pockets and pouches.  I recently had the awesome opportunity to hear Bethenny Frankel speak at a female founders’ event in NYC.  She was somewhat polarizing (there are actually some untrue and dramatic accounts of the talk that have been covered by a few news outlets – – see here) but I loved her pragmatism and can-do attitude.  One of the things she said was that “clutter kills creativity.”  She meant this both in terms of having a clear head and in terms of working in an organized space.  I couldn’t agree more.  I keep my bag pristine and organized, using a bunch of different Truffle pouches.  I love these document pouches ($44), where I can keep stray papers and receipts without folding them in half, and I recently snagged a third clarity pouch ($42) just for keeping business cards, as I’ve been amassing a ton while building my business.

 

+Great shoes.  I have always been an accessories gal.  Some women invest in great basics, like a fabulous YSL blazer or the perfect LBD from Victoria Beckham’s collection.  Not for me.  I’d rather go big on the shoes and bag.  Nothing gives me more confidence than the perfect shoe.  Lately, my Aquazzura lace-up flats ($675) have been giving me LIFE, y’all.

They are comfortable and fashion-forward in the best of ways.  I love pairing them with skinny jeans or a midi-length dress.  When I need to really empower myself, I wear heels.  I swear to God, these J. Crew Elsie pumps are the most comfortable, flattering heels ever — I own them in three colors and am just waiting for the right promotion to snag a fourth pair.

+DryBar + Manicure.  If I’m going to an important meeting or speaking at an event, I need a blow out and a good manicure.  These are small things but they seriously give me an extra boost of confidence to know that my hair and nails are on POINT, and that I am looking polished.  I had to give a talk to several hundred people about two years ago and I had the good fortune of receiving some 1-on-1 time with a public speaking coach.  He told me that half the battle is feeling like you’re prepared and said, “Wear whatever you’ll feel most empowered in.”  For me, this started with a good blow out and fresh manicure.  (I swear by either CND’s Cakepop, a light, opaque pink; Essie’s Lollipop, a cheery, orangey-red; or Essie’s Marshmallow, an opaque white.)  For refreshing your hair between sessions, I swear by DryBar’s Triple Sec (available in a tiny size that can fit in your bag on the go!).

+Good jeans.  You can spot a male entrepreneur out of a crowd by looking for a middle-aged dude wearing a blazer, expensive jeans, and loafers (often no socks) with a distinctive air of confidence about him.  It’s harder to spot a female founder.  I spend way too much thinking about whether a dress/skirt will be too feminine for a given customer or investor meeting and often wind up in dark wash jeans, statement-making shoes, and a blouse or chambray button down.  I’ve sworn by J. Brand for years but recently snagged this great pair from Frame Denim.  I guarantee that you will always feel comfortable in well-fitting, dark-wash jeans and some good heels, so it’s a good fallback.

+A watch.  I’m on a tight schedule every day, but it’s mega rude to be caught checking your phone when you want to make your customer, advisor, or investor feel as though they are the most important people in the world when you’re sitting across from them.  Casually glancing at your wrist is a much more elegant way to make sure you’re going in the right direction.  I wear my Hermes H Hour ($2,725) every day.

 

+My phone.  Amidst the chaos that is my life right now, I need my phone for several reasons:

a.  So I can call my mom.  I talk to her a few times a week and she keeps me sane.

b.  So I can text bitmojis to my sisters.  We are constantly sending each other texts and bitmojis throughout the day.

c.  So I can stare at my nephews using TinyBeans.  This is the most incredible app where my sister and sister-in-law will upload one picture a day of their sweet babies.  I LIVE FOR THESE PICTURES.  I could be in the worst mood, but taking a look at my little nephews makes everything OK.

d.  So I can kill time with Instagram.  I do spend a lot of time in cabs, cars, and public transportation shuttling from meeting to meeting.  Instagram is a great, brainless way to take a mental vacation while on the go.

e.  So I can (try, and often fail to) meditate.  I use the app Headspace to declutter my mind and it really, really helps.  It’s hard for me to commit to this in the morning when I just want to GO.

f.  So I can book workouts using ClassPass and blowdries using DryBar.  Seriously, booking through an app is the best thing ever when I need to make last minute changes.

g.  So I can keep myself on time.  I love the app Sunrise for managing my calendar.  It has handy reminders and a good integration with Google Maps so I can direct myself/my driver easily.

h.  So I can get an Uber whenever I need to.  I’m scared to look at how much money we spend on Ubers every week.

i.  So I can stay on top of my team using Slack.  The Slack app is rad and it gives me instant visibility into what our engineering and design team is up to.

j. So I can keep my to do lists organized.  One word: wunderlist.

+A lust list of things I am currently dying to own.  This gives me motivation to keep working hard so that I can eventually buy them for myself.  Right now, I’m trying to decide whether I’d rather replace my work bag with another tote (as outlined above) or save my pennies until I can get this Fendi, which I’ve long lusted after.  Also on my list: some new work flats (love my Aquazzuras, but could also use either these or these), a Burberry trench, and a YSL clutch.  But there are also nearer term fixes — less expensive treats to sprinkle in and reward myself with in the interim.  These include things like this J. Crew trench coat, which I just snagged on sale in the khaki color — enough to tide me over until Burberry days; this gingham shell (so chic and high-end looking, on sale!); this Zara OTS top; and this monogrammed clutch.

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