Tech Entrepreneur and Author Ali Kriegsman Shares Her WFH Secrets

Photo: Eva Zar Courtesy of Ali Kriegsman

Welcome to our monthly editorial series A Day in the Life where we ask successful women we admire to share the daily minutiae of their professional lives, from the rituals that set them up for success to their evening wind-down routines. This month we sat down with Ali Kriegsman, co-founder and chief operating officer of the venture-backed retail technology startup Bulletin and author of the forthcoming book “How to Build a Goddamn Empire,” which hits shelves on April 6th. Below, Kriegsman shares her unconventional definition of success, her go-to apps for staying organized, and her favorite WFH lunch.

Tell us a bit about your business. What whitespace did you see in the market that led you to found Bulletin? What need did you want to fill?

Bulletin is a premium wholesale marketplace where retailers go to discover and shop the best brands on the planet. Behind your favorite spas, wellness centers, cafes, boutiques, and gift shops is a whole hidden $300-billion wholesale economy you, the shopper, can’t see! Those stores—whether they’re physical retailers or online retailers—rely on various tools and services to discover brands and products their customers will love! Bulletin helps some of your favorite stores find the inventory they then sell to their end customers. We’re a business-to-business platform, meaning we don’t service individual consumers, but instead, we serve and support over 7,000 buyers and store owners who run these shops, and we have around 1,300 brands on our platform selling to these retail businesses. Our community is growing really quickly—and organically—so we’ll likely triple or quadruple those numbers by year’s end. 

We launched Bulletin’s wholesale marketplace because we actually used to be retailers ourselves! We were trying to solve our own pain point, while creating a more affordable way for the brands we loved to grow and scale, too. As a retailer running three stores in New York, we used so many different tools and platforms to find great brands and inventory—Instagram, Etsy, Joor—the list goes on. We felt like there wasn’t one cohesive place for us to discover, connect with, and source inventory from quality brands. So we built the solution we wanted to see in the world. Bulletin began as an e-commerce newsletter and pop-up concept in late 2014, early 2015—we did that for about two years before we ever opened our stores. And through that experience and those connections, we learned how insanely expensive it is for brands to get into retail.

Brands typically have to pay upwards of $30,00 (!!!) to showcase at a physical trade show to try and meet buyers. The operative word being “try;” there is literally no guarantee that if these brands pay that price tag, they’ll connect with or do business with retailers who attend. We also learned that vetting and paying for showrooms and wholesale reps was just as cumbersome and expensive for these brands. So with Bulletin’s wholesale marketplace solution, we kind of found a double whammy. 

We’d be able to help retailers like us find and source incredible inventory, and help level the playing field for independent brands all at the same time. We take a 15% cut on sales processed through our platform, so we literally only make money if we bring brands business. It is a wildly different format than the tradeshow, showroom, or wholesale rep route, and especially with COVID threatening those traditional retail channels, Bulletin has become a really attractive solution for brands and retailers alike.

Not only are you the co-founder and COO of Bulletin, but you’re also an author. Your first book, "How to Build a Goddamn Empire," hits shelves on April 6th. What compelled you to write this book and what do you hope people will take away from it?

When I was approached to write a book proposal, I actually knew exactly what I wanted the book to be about and the story I wanted to tell. As a first-time and inexperienced founder, I felt like I couldn’t relate to the glossy, glamorous entrepreneurs crowding my Instagram feed. I was 24 and I was seeing a lot of founders, especially female founders, posting incessantly about their wins whether it was press hits, awesome brand partnerships, rounds of funding. And honestly, I was doing the exact same thing! 

I think women entrepreneurs feel this pressure to be perfect. We’re fighting to hire great employees, maybe get some funding, secure those press hits and grow our businesses. Making everything seem rosy and easy can build that trust with your audience, and your customers, and I think women fear that being candid and vulnerable about the harder and more taxing psychological parts of entrepreneurship might put that growth or your reputation at risk. At least, that’s how I felt. And a few investors even told me that. Once I started getting more candid about my fear of failure, anxiety, depressive episodes, and struggles with our pivot from running stores to running a full-blown tech company, a female investor actually asked me to be a bit less “candid” lest I make the wrong impression or lead people to think I don’t know what I’m doing. She actually went so far as to tell me to “be more like X founder, be more like Y founder” and I found it really disheartening. 

But I didn’t listen. I decided to do the opposite.

I knew first-hand that building something from nothing is a confusing and emotional challenge you sign up for every single day. It's unglamorous, taxing, and endlessly stressful. It's a constant, dirty fight with your imposter syndrome and the intense fear that if things don’t work out, you've failed miserably. And publicly. I wanted to tell that story, so that if other business owners were suffering or worrying they’d fail, or that they were too incompetent to make their dreams happen, they could read my book and feel seen and supported. I wanted to create a counter-narrative to Instagram entrepreneurship and this glamorized hustle we’ve all come to know all too well.

So, while in the thick of scaling my business and a stressful pivot, I decided to write about my experience in real-time. I started writing the book in 2017 and finished it at the end of 2020. I was running retail stores in 2017 and 2018, a tech company by late 2019, and obviously had to stay alive and scale despite the pandemic in 2020. For that reason, the book really reads like both a relatable "how-to" guide and a candid personal diary (deep breaths), because it was written directly from the trenches and from the heart.

The book also features stories from over 30 other female founders who have built companies of radically different stages and sizes, too. By using the questions I'm most frequently asked as my guideposts, I offer candid insights into the nuts and bolts of building a brand from scratch—discussing early failures, picking the right co-founder, securing press, finding funding —to give entrepreneurs the tools that will help take their ideas to the next level. I feature interviews with incredible founders like Meena Harris of Phenomenal Woman, Trinity Mouzon Wofford of Golde, and Polly Rodriguez of Unbound. I’m so inspired by all of the women who are featured.

Most importantly, though, I am really trying to help founders, and especially women, redefine the word "success" with every single chapter. There is intrinsic and long-term value to building something of your own, whether you sell your company, crash and burn, or forever teeter on the precipice. My book argues that "success" has many faces, and sometimes learning, growing, and building something on your own terms makes you successful enough. You don’t need to get caught up in your impostor syndrome, compare yourself to other founders, or worry you’re not going to “make it.” I want more women business owners to love and appreciate the journey, rather than being so hard on themselves and thinking they don’t have what it takes to climb to the top. 

“Building something from nothing is a confusing and emotional challenge you sign up for every single day. It's unglamorous, taxing, and endlessly stressful.”

—Ali Kriegsman, Co-Founder and COO of Bulletin and Author of “How to Build a Goddamn Empire”

Are you a night owl or a morning person? When do you do your most important work and why?

I’m a total night owl. Sometimes I get wild bursts of energy at 11 PM and have to force myself to relax and get ready for bed. I wake up every morning at around 7:45 AM or 8 AM and relish cuddling with my dog and being lazy in the sheets for a while. The mornings are so precious to me. I use them to get my head straight rather than get work done. Candidly, though, sometimes if I’ve been working like crazy at night I sleep in until 9:30 AM and just own it. I used to have a nagging voice guilting me for sleeping in on a workday, but I’ve moved past that now.

I do my most important work after 7:30 PM or so when my entire team logs off. I find Slack to be extremely helpful but also very distracting, and I’ve always been someone with a limited attention span, so Slack culture really messes with me.

I love using Sundays to write. It was really tricky to juggle building a tech platform and pivoting Bulletin while writing this book. I found that Sunday mornings were the best times to write or get more “heady” and strategic work done. I’m using Sunday morning to answer questions for this interview as we speak!

What time do you get up? What’s the first thing you do upon waking?

I usually get up at around 8:00 AM. I’ll either roll around and cuddle with my dog, Winnie, if my boyfriend has taken her out already. If not, I’ll lazily throw on my shoes and a light jacket and take her for a nice walk. When I get back, I’ll feed the pup and get some coffee brewing.

I try to squeeze in a workout before my team logs on at 10 AM. I’ll do Chloe Ting or 305 Fitness, or just blast BLACKPINK and dance and lunge around my apartment. Now that it’s getting nice out, I’ll swap that for a beautiful run in Fort Greene park!

What does your morning, pre-work routine look like?

I’ll brew some coffee or make some iced coffee with Grady's (the best) and oat milk, decide what type of workout I want to do, and make a to-do list for the day. I always make a to-do list before my team logs on in the morning so I have my priorities straight and know what I need to cover or check-in with each of my direct reports. I use a platform called Notion to manage all my personal lists, thoughts, and priorities.

I always put on a podcast while I shower after my workout, usually “The Daily” by The New York Times or NPR’s “Up First,” so I can catch up on the news. My shower time in the morning is super relaxing and I love taking my time.

I’ve just started meditating, too, which has been a nice addition to my morning routine. I’m not doing anything crazy quite yet, but I’ve found a few great meditation videos on YouTube that I’ll queue up. It definitely helps calm and center my mind before the hectic workday, where I’m usually in back-to-back meetings and fighting for a quick break!

Mark Twain said, “Eat a live frog first thing in the morning and nothing worse will happen to you the rest of the day.” What’s the first thing you do when you get to your desk?

I clean out my inbox. I am obsessed with maintaining my inbox and keeping everything tagged and organized. I need a visual anchor for what’s going on, what’s urgent, and who needs what.  If I don’t clean out my inbox (I mean, honestly that literally never happens because I’ve been doing it for years now) but if I didn’t, I’d be a HOT MESS. My brain has to get it done before I can move on and focus on anything else!

What are you working on this week?

I’m launching my book in less than a week and also hiring about ten people to the Bulletin team. So my main focus this week is building out our hiring pipeline for all of our open roles, moving interviewees and candidates we love through the funnel and continuing to finesse our new org structure and role guidelines. As for the book, I’m prepping influencer book mailers, writing dozens and dozens of thank-you cards for those mailers, coordinating press with my publicist, creating assets for all the panels we’re hosting for the digital book tour, and just trying to keep the launch train on track. I actually love hiring and recruiting and I’m loving all of the work associated with the book launch, so even though it’s a lot, I’m in a great place and groovin’ along.

What’s been the most rewarding part of running your business? The most challenging?

The most rewarding part of running my business is managing our incredible team, and building a technology product together. We work with so many employees, particularly women, that have been with us for nearly three years and who have just grown and blossomed into such remarkable assets for the company. And they’ve become amazing role models and influences to the more junior employees on the team. I actually went into Bulletin thinking I’d despise management. I’m somewhat of a lone wolf and have always been that way. I was the girl who took over group projects and has always loved juggling various roles and responsibilities solo. But helping these women evolve, learn new skills, and come into their own as leaders and managers has been such a blessing.

The most challenging part of running my business is honestly just keeping my head up. This stuff is really hard. Building a tech company and running a tech platform that thousands of people are using every day is a new journey, for sure. I am on the front-lines with our customers because I run our Growth Team, and my team is in charge of growing our revenue month over month and hitting our targets. I get impatient when we can’t develop or fix the product fast enough. I get anxious when we get negative customer feedback. The pressure to keep growing and to deliver excellence to our customers is something I take really seriously. Sometimes I wear the pressure well and sometimes I just don’t. I’m working on it, but yes, I think the most challenging part of building a technology company and growing this platform is staying positive, light, and optimistic when things go wrong.

Do you ever reach inbox zero? How do you handle the constant influx of inquiries and communication entrepreneurs are so familiar with?

I never reach inbox zero. I try to set boundaries with myself and with my team. My team now knows what to email me about versus what to Slack me about. We try to use other tools like Monday and Coschedule for project management so we aren’t bombarded with Slacks or emails left and right.

I have gotten really good about blocking off time on my calendar when I need a strategy session or a break from the Slack craziness. In those blocks, my team knows I’m head down working on a project or chatting and planning with Alana, my co-founder, so they don’t ping me or communicate with me during those times. 

I’ve gotten comfortable with the fact that I’ll never be at inbox zero, especially during COVID. People, myself included, are juggling a lot and just trying to stay above water. Maybe pre-COVID I wouldn’t let certain emails sit in my inbox for days on end, but now, I’m all about prioritizing who I get back to first and why, but I’m also good at prioritizing myself and choosing to shut my laptop off at 8 PM instead of feeling the pressure to get back to everybody so urgently.

“There is intrinsic and long-term value to building something of your own, whether you sell your company, crash and burn, or forever teeter on the precipice.”

—Ali Kriegsman, Co-Founder and COO of Bulletin and Author of “How to Build a Goddamn Empire”

Photo: Eva Zar Courtesy of Ali Kriegsman

What is your go-to work lunch?

I typically microwave some frozen brown rice, make a Beyond Meat breakfast sausage patty (it's SO good), and throw it on top of the rice with half an avocado and a runny egg!

I also make salmon a LOT because it’s so insanely easy. It’s a great thing to have in the fridge if you have a busy schedule but want to eat healthy and avoid spending too much cash on delivery. I buy a ton of frozen salmon fillets and keep them in the freezer, so I can easily defrost them and bake them for 30 min on 300 degrees for dinner. Sometimes, for lunch, I’ll do that leftover salmon mixed with some lemon and mayo, and slap it on some multigrain toast. Tuna salad, watch your back - there’s a new fishy salad in town.

Okay, last one. I also always have Tyson crispy chicken in the freezer. I am a total sucker for chicken tenders, crispy chicken fingers, and pretty much crunchy crispy oily chicken in any form. I’ll pop a Tyson tender in the oven for 20 minutes, and then put it in a whole wheat wrap with avocado, my favorite Kensington garlic sauce, some arugula, and some melted cheese. It’s absolutely delicious, pretty healthy, and satisfies all my cravings. 

What advice do you have for balancing the minutiae of day-to-day tasks with big-picture planning?

I am honestly somewhat bad at this and am trying to get better. Because we’re growing so quickly and hiring and building, I get pulled a zillion different ways and have so many tasks that pile up throughout the day. It is a big goal of mine to continue to delegate more, build in time for myself to think and strategize, and get myself out of the minutiae as much as I can.

What are some work habits that help you stay healthy, productive, and on track to reach your goals?

I have been making to-do lists and priority lists for as long as I can remember. I keep different to-do lists in Notion for my book, my personal life, Bulletin, and even keep a real-time log of my thoughts as they come up, whether it about my career, my team, work, or whatever. I find that my mind tends to race a lot so I’m able to stay productive by translating all my thoughts to paper and getting them out of the ether of my mind.

I’m also good about making time for myself, even if I can only squeeze in two or three hours to myself a day. I make time to work out, I make time to go outside and on walks in the park with my boyfriend and my dog. I make time to cook, which I find super relaxing. I make time to listen to music I love and watch compelling documentaries or movies or TV shows. I don’t believe in the endless hamster wheel and have had a full breakdown before when I work too hard and don’t make that time for myself. Rest is important. Scheduling time to relax and process your life is important. And doing it consistently is key! Don’t just make time for yourself when you feel you’re about to erupt. Do it on the daily so you prevent those breakdowns from boiling over. 

Any favorite apps you use regularly?

I use a new platform called Norby to organize all of my link-in-bio information and also manage and promote all the digital events I have coming up for my book. It is so insanely easy to use and it is such a flexible and intuitive platform that I’m able to run so much of my life on it. It’s great.

I obviously use Instagram a lot because I’m running a business and launching a book, but I’m trying to be a bit more mindful of how often I end up aimlessly scrolling and comparing myself to other people. Trying to pivot to use IG for business-only, and really reclaim my free time and headspace! For business, though, I use Canva and Planoly to design and plan my content. I am obsessed with both and find them both really easy to use.

I use Hotel Tonight if I need to get away. I use it once every two months or so and book myself an affordable hotel room in NYC or Brooklyn. I love my boyfriend and my pup and our life in Fort Greene is delightful, but with COVID, I find myself getting this urge to break away and get a change of scenery. Hotel Tonight makes it super easy and I’m usually able to find a hotel for around $100 bucks for the night. I’ll order Seamless to my room and totally indulge and bring a bottle of wine and just chill. It is a miracle app and it has been such a source of self-care for me.

What are you reading, watching, or listening to right now to help you wind down at the end of the day?

I am obsessed with: “The Great British Bake Off,” “Law and Order SVU,” “Ted Lasso” (SO GOOD), “Criminal Minds,” and cheesy true crime Lifetime movies. Honestly, throw me a true-crime documentary, an upbeat buddy comedy, a melodramatic movie about a cult, or a dark psychological thriller and I’m good to go. I’m also a total sucker for WW2 in Color documentaries or mini-series. I watch a LOT of history shows. Sometimes I like watching TV shows and movies that are super mindless and really let my brain release. Other times I like learning and digesting information. It varies.

As for what I’m listening to, I just finished a crazy podcast called “Mommy Doomsday” from Dateline. It’s true crime. Absolutely wild. I also listen to a lot of political podcasts like “Pod Save America,” “Pod Save the World,” and just started “Us&Them” and “Sway!”

As for what I’m reading, I have a rotating list! I just finished Leigh Stein’s “Self Care” and am in the middle of Jenny Odell’s “How to Do Nothing” which I’ll dip into during the week, usually with a bath and a glass of wine. I am reading “Caste” by Isabel Wilkerson on Sundays when I want more time to read. I’m about to dig into “More than Enough” by Elaine Welteroth and if I’m feeling spooky I’ll pick up “The Perfect Nanny” by Leïla Slimani. It is so, so scary but so captivating. 

When do you go to bed? What’s your “optimal” number of sleep hours?

I need at least 7 1/2 hours. My body doesn't function the same with less than 7 1/2 hours. I get cranky, I’m more sluggish and lazy and my whole energy is off. My boyfriend can sleep like 5 hours and be fine which *blows my mind.*

Lately, because I have a book launch coming up and Bulletin’s been crazy, I’ve been working from 9 AM to 10 PM or so. I need about two hours of me-time every day at least, so I usually end up going to sleep at 12:45 AM or 1 AM. I wish I could go to bed earlier, and under normal circumstances, I would, but as a night owl, I get my best book and Bulletin work done from 7 PM to 10 PM, so I need that 10-to-midnight window to do my thing and chill before passing out.

What’s the most rewarding part of your day?

Ending a long, bustling day with my boyfriend and my dog, turning my phone on silent, and cozying up to a book or dinner and a documentary. I cherish my free time so insanely much because as I’ve advanced in my career, that “me” time window gets smaller and smaller. I’ve learned and accepted that sometimes, you go through massive “sprints” in your life where you’re lacking the right balance of work, play, and chill. Right now, I’m in one of those sprints. I feel so extremely fortunate to be launching a book and running a company, and I know there’s a light at the end of the tunnel once this book is out the door and Bulletin has settled into this new growth phase. But for now, I have mini “lights” at the end of every day’s tunnel because I have a partner and a pup who embrace me at night, hold me, shower me in love, and make the day’s stresses disappear.

“How to Build a Goddamn Empire” by Ali Kriegsman

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