My perspective on how to live the risky startup life without being at risk.

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Painting by Wayne Thiebaud

Job skills: Finding them. Resilience. Comfort with short-term uncertainty.

The year I ripped a hole in the cartilage in my hip was the year my first company imploded. En route to Oregon to cheer for my triathlon team, making the most of a deep disappointment, my company went bankrupt.

When I landed for my layover in Portland I had voicemails, emails, and texts from my boss and the CEO. I rang my boss.

You should probably sit down.

I’m rushing to a connection.

Well, then steady on your feet….

The CEO had gathered everyone in the cafeteria to tell 150 people they were unemployed, that everything he and they had worked long hours to achieve was halting. Two weeks severance.

I ran-limped across the Portland airport a little after noon, listening to my boss deliver the details. My account would be cut at 7pm and I’d lose access to my email, contacts, and documents. My boss would collect my personal belongings so they wouldn’t be auctioned or trashed. It was June 30 and my health insurance would end that night.

Does my direct report know?

I’d hired a fantastic young lady a few months prior. She was 6 months pregnant now so would be unlikely to find another job soon. She’d been alone without a team at the announcement. I was flying to Oregon and my boss was out of town.

Good idea to call her, but she was in the all-hands. At least unemployment pays more when you’re pregnant, and her husband has a job.

At least. And my team of consultants?

You can ask them to submit their invoices, but it’ll be a battle to get them paid.

                                                                  * * *

My boss had known for a week, or at least suspected. A week before she’d sent me a cryptic text message, early one Sunday morning, telling me to turn in my expense reports immediately. I’d travelled literally around the world for user studies and conferences in Asia, Africa, and Europe. I’d been back a week and was still plowing through the expense list.

Don’t ask questions. Just finish it today.

She had never asked me to work on a Sunday, so I had dropped everything without asking questions. I’d spent my Sunday finishing the report. She’d saved me thousands of dollars.

My triathlon was near Bend, Oregon, which has a beautiful cafe with book-lined walls, live classical piano music, and tea with scones. There’s nothing like live classical music and hot tea when you’re racing to copy every contact out of your email, download every document you might ever need, and secure health insurance.

                                                            * * *

I told her I could come and get my belongings from the office myself after the triathlon, but she pushed me not to wait.

It might get removed by then.

It’s a lot of stuff.

I don’t care if you have extra bras in the locker room. These are extenuating circumstances.

I had half my wardrobe in the locker room. I biked 15 miles a day and didn’t want to carry my clothes, shoes, shampoo, and makeup every day. There were dresses, boots, curly-hair creams, and extra bras.

Wow. It looks like you were homeless and living at the company.

                                                                * * *

A forward-thinking employee gathered our personal emails to share, so we wouldn’t lose contact with everyone forever at 7pm.

I called the consultants.

I’m afraid the company declared bankruptcy, and I know we still owe you some money.

I’m so sorry to hear that; let me know what you’re looking to do and I’ll help find you a job.

They were excellent consultants.

                                                                   * * *

Shawn drove up to buy me a sushi lunch and offer an especially poignant barrage of anecdotes and advice.

What did you learn? You learned that if you want to work in little companies, you need to balance your lifestyle and savings to be able to subsist for six months of unemployment. You learned to always keep your network primed so you can call in job-seeking support at any moment. You learned to always submit your expense reports immediately.

Did you hold onto your laptop? Don’t turn it in until they’ve paid you anything they owe you.

Did you start a LinkedIn group for the employees? In two years you’ll have a friend in every company in the Bay Area.

It happens that I’ve been studying the top ways companies find candidates, so I’ll send you required reading on how to place yourself so they find you. You’ll optimize your LinkedIn profile for hiring searches, and you’ll create a target list and brief personal overview to bring to all your coffee meetings, and to forward to all your supporters. I give homework.

Oh, and the sushi is on me.

I found my laptop on eBay for $350 and told my boss I’d rather pay for it than return it. The company never came for it. I went by her house and picked up my office supplies, my jacket, my desk chachkies, my toiletries from the shower room, my shoes, my extra underwear and dresses in case I forgot to bring clean ones on the bike, my…

She was not just a good boss. She was also a good friend.

I started a private LinkedIn group for all the former employees where we could share job postings and news. Soon those 150 people were dispersed across 100 companies; the best network I’d ever had.

I asked each of the executives to have coffee with me and explain to me what had happened to the company, what had gone wrong, how it had unfolded. I wanted to learn about business, and about managing a team in crises. I wanted to learn from the similarities and differences in their stories. I’d loved my work more than ever before in my life, but if it was gone at least I was going to achieve a thorough education.

                                                                    * * *

Three years and two jobs later I was the tenth employee at an innovative startup. I’d finally had hip surgery and was still recovering. I had six months of buffer in the bank, a volunteer gig with an incredible network of angel investors, and all my clothes safely stored at home.

Six months after I joined that startup we’d doubled in size to twenty, but something was wrong. There were politics. There was no product. There were leadership issues. This time I was more sensitive to the signs. This time I was more prepared.

It was a Friday and I was home sick, but I was restless. I couldn’t relax to read or nap. Instead I finished my expense report from a recent work trip to Australia and submitted it, then backed up all my contacts out of my work email to my personal one. I downloaded my personal documents and saved them on my own computer. I was waiting for the copying to complete when one of the CEO’s lackeys sent me a message.

How sick are you? Could you come in for a critical meeting now?

Does it have to be today? I’m actually sick.

Yes, it has to be today. How soon can you be here?

I set my company laptop on my coffee table to continue copying and took the train downtown. Half the company was gathered in the office looking solemn and confused; the rest had been told to stay home and were messaging us, also confused.

One of the CEO’s lackeys grabbed my arm and looked at me like he was going to cry. They handed us each a manila envelope with a contract and a check, a huge check in exchange for a small contract swearing ourselves to secrecy.

Our group was dazed, angry, upset, surprised. One of the employees told to stay home had ignored the message and was there; he couldn’t figure out whether he still had a job.

Only a couple of us had been through this before. I’d learned. I found a notepad and pen and asked each person to record their personal email since our accounts would be eliminated. People opened their laptops to quickly remove personal items before they were confiscated. One of the CEO’s lackey’s approached me.

I need your laptop.

It’s at home. I was home sick. I didn’t bring it in for this meeting.

I need it.

I’ll have to give it to you another time. By the way, I submitted an expense report today.

We went for drinks at Comstock Saloon. A few shell-shocked employees who hadn’t been let go watched our accounts on Slack go blank one by one. They messaged us to ask what was happening, and noted they also felt a strong need for a strong drink. We gathered in the saloon for our mid afternoon cocktails.

It was the beginning of the end. Within a year there would be only one person left from that original team of twenty, and it was not the CEO or his lackeys.

I started another private LinkedIn group where we shared jobs and news, and from which we could watch where our colleagues landed. This time I had money in the bank for six months. I had a strong professional network, and I’d kept track of many companies and jobs that interested me. I looked up those companies and checked their job postings, or reached out to leaders in my areas of interest regardless of their openings. I had coffee with everyone I knew, and asked them to send me to have coffee with everyone they knew. I looked up all the recruitment emails I’d received in the past year and reached back out to them. I made a one-page overview of my targets and background to leave with all the coffee dates, and forwarded it to all my connections.

I did not sit down for hours alone at the computer, to make thorough overviews of my industries of interest, all the companies that were growing, all the jobs I could do. Instead I had a list, a rolodex as Shawn loved to call it, of all the people I knew who might support me. I had examples of companies of the type I liked, and a couple clear descriptions of positions I sought. I searched job sites only when a contact suggested a new company, and I applied only through referrals. I was honest about what I sought, even if it didn’t fit a standard mold: Well-respected leadership, above all. A healthcare business with a sustainable model. Deep awareness of the politics behind the business of healthcare. The largest company where I could be at a level to work with the CEO. A culture that encouraged individual initiative and gave individuals responsibility based on the results they delivered, not age or time or politics. A place where every person who interviewed me was one from whom I could learn something.

On the trail to find such a company, I met an incredible string of people, and I learned from every one of them. Because I was confident, had (a few) clear definitions of what I wanted, and was happy for advice or connections even without an offer, everyone was happy to talk to me. Through our conversations I learned about fascinating leaders, businesses, and technologies. I made a commitment to myself to continue these coffee meetings when I was employed, not just to find jobs, but for the stimulating experience and valuable insights.

I found a few amazing jobs. Two offers were objectively exceptional, but the culture wasn’t quite right. After one of the angel investor meetings where I volunteered, Anne recommended that after I receive an offer and before accepting, I ask to either do a project with the company or shadow someone for a day. There was no other way to know whether I’d fit with the team and manager. Following her advice, after I received offers I asked for these opportunities. The companies were usually skeptical but open.

Then I found a job description that didn’t precisely fit my targets, but was interesting and was at a company that seemed a perfect fit. I wrote to Anne:

I want this job. It’s the right fit for me. You’ve invested in the company. Could you introduce me to the hiring manager?

Instead of a reply I was copied when she forwarded the email.

It will be a big mistake if you don’t talk to this candidate. See below.

I interviewed, then left for Guatemala. After all I had six months buffer in the bank and it had only been three. I got the offer.

Being in Guatemala, I couldn’t shadow or do a project at this company, so I had to trust my instincts that it was a good fit. It was just as well, since the hiring manager left a few days after I joined. I seem drawn to companies at stages of exciting growth and inherent instability, but I’ve learned to put a buffer between their teetering and my life. Today I have six months in the bank, coffee dates but not as many as I’d like, and a volunteer gig with Anne’s angel investors. I try to submit my expense reports quickly and demand invoices from my consultants on time. I give what I can to my network, knowing that life and careers are built on personal relationships not resumes. I use the skills I learned living abroad to find ways to keep in touch with professional contacts, just as I did when trying to maintain friendships and family ties. And every time an instability presents itself I try to learn everything I can about how it came to be and how it was managed.

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