The Scotch and Bailey’s Are Still Sealed - How Entrepreneuring Has Differed From What I Expected - rocketMBA
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The Scotch and Bailey’s Are Still Sealed – H...

The Scotch and Bailey’s Are Still Sealed – How Entrepreneuring Has Differed From What I Expected

Especially in San Francisco, startup culture is often portrayed as (and at times is) full of coffee-shop-posturing, WeWork-humble-bragging and blanket optimism.

Not here.

This is an honest and vulnerable account of my journey to start a business and navigate the ups and downs along the way.

I feel a little uneasy telling this story publicly but it’s important to me because in startup blogs and conversations I see a lot of two things:
* Early stage founders full of saccharine pride: “oh we’re crushing it, it’s awesome!”
* Or, successful veteran entrepreneurs humbly reflecting on the early days: “it was tough at the beginning, fortunately, we persevered and eventually succeeded!”

Private conversations with entrepreneurs and freelancers have taught me that we face a lot of the same frustrations and joys, but not much is written about the ups and downs in real-time.

This is my attempt to change that: I want to demystify entrepreneurship and shine a light on my journey in real-time. Day to day what does it look like (and feel like) in that time before… Traction! Momentum! Product-market-fit! Cash-flow! Success!

So here goes:

I am working with a partner (let’s call him Bob) and we focus on services to make life better for older adults at home and their circle of loved ones. We met at business school and we worked and lived together for two months this summer when Bob sublet my guest room. Later, he got a day job to cover his bills; now we work together via email and weekly sync meetings until we can get funding.

We’ve had many ideation sessions and evaluated multiple ideas. We are still searching for the right one.

We approach it like a search fund seeking an acquisition or an investor doing due diligence: dive in, research, talk to people, evaluate, do some red team-blue teaming, and try to kill things quickly and move on. While this approach is efficient (better to quit something after 6 weeks than to wake up 6 months in and realize it won’t work), the constant false starts can feel like mini-failures, and that’s tough.

Still Waiting for the Right Moment to Open the Scotch and Bailey’s

I thought Bob and I would hard-charge the startup idea, working morning to night, shoulder to shoulder, brainstorming, researching and building something. I expected days full of whiteboard time, spreadsheets, pitch decks, customer interviews, and more than anything else: progress and momentum toward a vision. The day we kicked off in June, I bought a bottle of each of our favorite drinks (Scotch for him, Bailey’s for me) to celebrate a milestone like our first customer or fundraising, or launching a pilot.

They’re still sealed.

While it hasn’t been what I expected, it has not been wasted time either (though it can feel that way sometimes). I’ve loved a lot of it, learned a ton, and been surprised by things.

I’ve Loved…

Inside the startup project:

Forget what others expect, I’m charting my own path. After years of doing what others expected of and wanted for me, it’s relieving and uplifting to self-direct my next moves

Embarcadero walks are more inspiring that I imagined. Bob and I have a great rapport in our brainstorming sessions. They started in Bass Library conference rooms and moved to my living room dry erase board and city walks. I feel most productive and inspired when we are hatching plans and asking big “what ifs” together on a walk-and-talk along the Embarcadero. It seems possible to make the world better.

Never because “the clients asked for it”. Doing work for a sense of personal meaning and satisfaction, rather than just because clients asked for it or a boss assigned it is amazing. (Bob and I are both former consultants).

Outside of the startup project:

Turning off the wake up alarm. Waking up without alarms and feeling fully rested (for the first time as an adult) is transformative. My outlook on the day and my own sense of self are 20% more positive when I’m rested!

Time for friends and water bottle portraits. I want travel, reading, photography, friendships, and healthier eating in my life. When I worked before b-school, I never made social plans on Monday to Thursday because work was exhausting and unpredictable. Now, I can join friends for meals, conferences, and walks. A friend let me test drive his mirrorless four-thirds camera during a trip to Europe and I spent hours taking “portraits” of a bottle of Evian water in a square in Copenhagen to experiment with angles and depth of field. It was a blast.

I’ve Learned…

Sometimes I work in my pajamas all day and that has taught me about my ideal working conditions.

I work best as half of a dynamic duo. I prefer teams over contributing as an individual. While I crave solo time to recharge, I do my best work when I am supporting and supported by others, when I am trusting in and trusted by others. I’ve accomplished things I am proud of with a single partner in crime. Day to day, it feels like I’m working solo, and that’s tough for me. To fight the loneliness, I nurture my friendships through coffee chats and Skype dates to stay connected and draw energy from people I care about.

My recipe for productivity includes structured time and a rhythm. When my calendar is a blank canvas, I’m less efficient. In school, I often had 50-60 hours between Monday and Friday booked on my calendar for class, activities, meals, errands etc. I was speeding through life at 100 miles per hour. And I liked it. I was – and I felt – productive, efficient, effective. Now I have whiplash from the rapid deceleration. These days, less than 20% of my time is pre-scheduled; most of my day is open. I’m experimenting with time blocks at cafes and libraries as well as self-imposed deadlines and setting routines like working out or calling my family the same time each day.

I’ve Been Surprised By…

Loneliness is the dark underbelly of independence. For me, working from home is lonely. Working alone hour-by-hour is lonely. There are days I don’t leave the condo. There are days I wake up, munch cereal, and do emails on my laptop in bed all morning. No one’s here to see or judge. I fear this is eroding some of my discipline, my go-getter-ness, my sense of self. This isolation tax is far greater than I anticipated. I thought I was alone in this feeling, but have since learned this is quite common in the first 6 months of working from home.

I never thought I’d miss having a boss, but … I yearn for the satisfaction and validation of a manager’s appreciation. In my old job, if I got a “nice work, thanks for pushing this to the finish line” as an email reply from my boss when I delivered work, it could make my day. I knew I had successfully completed a project. At school, there was so much feedback, honesty, and support. I knew where I stood with others and felt appreciated and seen. Now, I don’t have a boss to acknowledge or congratulate (or critique me) for my work: surprisingly, I miss it.

To paraphrase Zoolander, there’s more to life than being really really ridiculously good at working. “Duh!” some of you are saying. I suspect each of us hears others say it and until we each have our ah-hah!-moment, it sounds pretty abstract. In the US, we strongly link our identity with our work — “what do you do for a living?” is such an early get-to-know-you question. Not too long ago, I believed that work and sleep were and ought to be the two main buckets for my time. Now, I see my time as a mosaic with tiles of different sizes, including family, hobbies, community engagement, professional pursuits, healthy lifestyle, and happy relationships.

I used to think bold ambition was arrogant. Now I don’t. To say it bluntly: I would rather fall short trying to take a Big Swing at something really impactful to the world than to succeed working on something safe or small. I did not think that way a few years ago, and I certainly would not have declared it aloud two years ago. Thanks, business school, for an outsized dose of self-esteem and ambition. Now, I want to harness and direct it toward a meaningful project!

The voyage has only just begun! Stick around for more learnings, loves, and surprises.

Holly MayHolly spent 5 years a strategy consulting for medical product companies and can bend Powerpoint to her will. She recently graduated from the Stanford Graduate School of Business. She and her husband returned to SoMa, San Francisco where she enjoys her own corner office (aka the kitchen table), takes pride in her indoor plants, and keeps the DVR full of crime and mystery shows.


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rocketMBA is excited to have fantastic guest contributors who share their research, experience, and stories with us. This blog is a platform for great doers, thinkers, and leaders to discuss their lives of business and the business of their lives. Opinions expressed by guest contributors are their own.

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