Ali Kriegsman - How to Build a Goddamn Empire: Advice on Creating Your Brand with High-Tech Smarts, Elbow Grease, Infinite Hustle, and a Whole Lotta Heart

For Mom, Ben, and Alana

In memory of David Getman, who never doubted me when I doubted myself. I miss you every day.

Editor: Samantha Weiner

Designer: Jess McGowan

Production Manager: Rachael Marks

Library of Congress Control Number: 2020931089

ISBN: 978-1-4197-4290-3

eISBN: 978-1-68335-809-1

Text copyright 2021 Alixandra Kriegsman

Cover 2021 Abrams

The interviews in this text have been lightly edited and condensed for clarity.

Published in 2021 by Abrams Image, an imprint of ABRAMS.

All rights reserved. No portion of this book may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, mechanical, electronic, photocopying, recording, or otherwise, without written permission from the publisher.

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If you are reading this book, you may have decided to start your own business, build your own brand, make a radical career shift, or pursue a once-distant dream. Whoever you are, youve likely decided to make some sort of big life change. Or maybe you havent quite decided yet, but youre plagued by what ifs and a short list of roads not taken; youve spent hours, months, or years pining for a more fulfilling work experience but have put those aspirations in a nice little pile and told yourself to look away for now. Maybe you have a passion you wish to turn into a career. Maybe you feel trapped in some drab-ass 9-to-5 and wonder, Is this really it? But like... really though? Maybe youre currently unemployed and looking to break into a brand-new industry, or youre cobbling together a handful of part-time gigs and looking to pickor createa profession where you can grow and establish yourself. Wellwhoever you are, and whatever brought you here, I want you to know where I stand. I want you to know how I feel. Because I was once a nine-to-fiver who felt unfulfilled and wanting, staring down the scary prospect, and implications, of a big life change, too. But I am not a self-empowerment guru who wants you to find your inner girlboss. I dont think Ive found her. I dont try to manifest or actively practice any sort of positive thinking. In fact, I cant stop myself from the practice of negative thinking. I dont believe that hard work and resilience equals a foolproof recipe for success. Ive seen hardworking people fail. Ive worked my ass off and failed big-time. And I dont think running your own shit will suddenly bring you unadulterated, toxin-free happiness. I dont have it. Thats not what you should expect, despite what influencers, inspirational Instagram accounts, and even other entrepreneurs might be peddling. I want you to know that doing something new is hard. Building your life around any entrepreneurial effort, if youre doing it seriously, will feel like an emotional and intellectual Cyclone drop. Because building an empire doesnt happen overnight. And you may get few or no early signals that it will even happen at all. That shit sucks. No number of motivational sticky notes plastered on your mirror or afternoon affirmations will change the fact that sometimes, being your own boss and paving your own way feels like a total. fucking. hellscape.

I cant give you a three-step manual for how to deal with your hellscape moments, because there isnt one. And I cant share any cutesy, pithy mantras to make you feel like a #badass in your times of self-doubt or hardship, because in my experience, they dont really work. But what I can do is tell you whats coming, as candidly and as openly as possible. I can share my moments of weakness, of desperation, and of total and utter fear. I can tell you what I think I did right and what I definitely did wrong. I can introduce you to dozens of other entrepreneurs who turned hellscape moments into learning opportunities. And I can show you that no matter how big a business gets, how many fans it has, how much money it makes, how much funding it takesno one is spared the rollercoaster ride of uncertainty and defeat, of mastery and euphoria.

Almost every founder Ive interviewed, with some prodding, spoke openly about what I call their Im-gunna-fucking-quit moment. Actually, make that moments, plural. Theres a real bleak side to entrepreneurship, and I think all of us (but women especially) have been trained to suffer these depressive episodes alone. We are ashamed of them, because it isnt cool or sexy or inspiring or boss-like to address these hurting times head-on. Social media has only exacerbated the problem: every day, you open your Instagram feed to household-name founders decked out in designer getups, youre fed power mantras from uplifting, candy-colored grid posts, you see other entrepreneurs all-smiles on their stories as they rush from meeting to meeting. Female founders, in particular, are quietly expected to both govern and influence, run their companies and build a personal brand. Often, these personal brandsmine includedexude empowerment, an effortless sense of perfection, and an unyielding stylishness. There is minimal messand when there is, it can feel calculated, an Us Weeklystyle reminder that successful founderstheyre just like us! All the while, you may feel a deep, unshakeable sense of inadequacy. You may be home, stuck on the couch, overcome by so much darkness that even the thought of power-strutting into a meeting feels overwhelming. Or maybe youre genuinely broke, running out of cash in both your personal and professional bank accounts. Its really hard to feel like youre on the right track when you measure your own financial reality against immaculately styled IG outfits and get that bread money memes. My company, Bulletin, can reluctantly count itself as part of the problem. We have both promoted and shaped the girlboss ethos so many of us have come to loathe. We posted those money memes. I still wear the fanciest shit I own to panels and public events. And because all of us are flexing in our own ways, in different doses, its become too easy and automatic to compare yourself to other people. Founders rarely cry, scream, sulk, or stream their distress on the air, so to speak, so when youre at your worst, you feel like a total loser. A weak-willed failure. Impostor syndrome takes hold and convinces you of the sinister lie youve been telling yourself from day one: I dont know what the hell Im doing, and Im not equipped to do this. It crawls its way up through the muddy bowels of your self-doubt, looks you straight in the eye, and asks, Who do you think you are?

Whatever change youre about to embark on: a new venture, a side hustle, a brandyou name ityou are signing up for struggle. You are signing up for days riddled with anxiety and uncertainty. You are signing up for problems you dont know how to solve, and for mistakes that might make you feel incompetent and foolish. You will feel pain when something goes wrong and you let your team or your customers down. You will feel pain when you run out of money and youre not sure the business can survive. You will feel pain when you turn down birthday dinners or happy hours and disappoint your friends because you have orders to fulfill or a crowdfunding campaign video to finish. When you are working on something you love, something thats yours, your highs become higher and your lows become lower. The pain feels like an 18/10. Being an entrepreneur means you have an unpredictable and endless stream of these 18/10 moments, really. Often, theyre prompted by triggering events or experiences: you lose an important client, screw up a pitch, or cant make payroll. But theres also a more insidious, lingering pain thats always there, humming below the surface. This pain has a voice, and it talks to you: it worries about failure, and what happens if your dream simply... doesnt work out. Wrestling with that voice is the hardest struggle of all.