A week in the life of a startup CEO (highs and lows)

Here's a look at my life as a startup CEO during the first week in October.

What's happening: The first week of October began auspiciously and ended on a low with me resting in bed for a week afterwards.

So what happened?

Thursday. My wife and I drove from San Francisco to Calistoga for a Tech CEO Retreat hosted by Bridge Bank. The private event was held at the Solage Resort & Spa.

After lunch, I attended "VC Panel: Trends in Technology and Venture Capital."

It was moderated by Dan Primack of Axios with participation from Venky Ganesan, Partner with Menlo Ventures, and Bill Coughran, Partner with Sequoia Capital.

Last year I blogged about it; this year all comments were off the record. 

Later that evening, we enjoyed a delicious meal under the stars, sans roof.

Seated next to me was my new Kiwi friend, Derek Callow (CEO, Swimply). Across the table was another new connection, Ethan Agarwal (CEO, The Coterie). I discovered the term remnant inventory from Ethan that night.

Selfie with Derek Callow and Ethan Agarwal

Friday. Day two of Bridge Bank's Tech CEO Retreat started off with sampling the resort's Olympic-size pool with my wife.

After breakfast, we headed over to Frank Family Vineyards for wine tasting.

We didn't stay long, as I needed to head back to SF for an afternoon event.

It was a solid two-and-a-half-hour drive back to our SF office. I was a few minutes late meeting my cousin and now Executive Assistant, Rich Mansfield.

He'd flown in from Idaho for the day to help me with logistics for our inaugural Paubox Kahikina STEM Scholarship SF meetup.

We picked up pizzas down the street, got some water at Trader Joe's a few blocks away, and tidied up the office. 

Eric Nakagawa and his daughter Chichi were the first to arrive, they got there ten minutes early (love it). Nick Wong and Jada Lee showed up a few minutes afterwards.

We eventually reached quorum when Logan Lau, Landon Choy, and Koa Chang made their way up to the city from Stanford.

The purpose of the meetup was to introduce our scholarship recipients to advisors Eric Nakagawa and Nick Wong. Q&A was encouraged.

A fireside chat with Eric Nakagawa and Nick Wong

Saturday. By the time Saturday morning came, all I wanted to do was sleep. Such was not the case, as we had family in town and I had a flight to catch that afternoon to Las Vegas.

Next stop, the HLTH conference.

I took an Uber from the city to SFO and whizzed thru airport security via the TSA PRE line. 

Also managed to read a few chapters on the flight. 

Upon landing, I check into my room at Hilton Resorts World and promptly crash out.

Sunday. I'm again wanting to catch up on sleep. Feeling exhausted. No such luck.

I meet Dean Levitt at our booth at the Las Vegas Convention Center West by 9 A.M. for setup. 

Dean Levitt

By the time I'm back in my hotel room, there isn't any time to sleep. Our booth officially opens at 1 P.M.

Dean and I are back at the booth for the 1 P.M. opening, as are Greg Hoffman and Jordan Holmes.

Dean Levitt, Jordan Holmes, Greg Hoffman (Let's go sell some software)

Our coworker Rylie Mahoney got the runaround on her flight out to Las Vegas; she joins us later that evening for the HLTH welcome reception party.

Monday. Although it's technically day two, this is game day. We're all early to the booth for the 8 A.M. start. We're now fully assembled, ready for the nine-and-a-half hours of event time.

Greg Hoffman

Selfie with Sal Lo (CEO, Jorie Healthcare Partners)

It's not a healthcare conference without Mike Parisi (Head of Client Acquisition, Schellman)

Enjoying a beverage at the end of day two on the conference floor with Greg Hoffman

Before the day is out, I write a blog post from my bed in the hotel room. 

Still exhausted, but on a natural high from meeting customers and prospects.

Tuesday. Last day of the conference. Another 8 A.M. start, with another 5:45 P.M. ending.

Completely on fumes now. Screw it.

Get up. Dress up. Show up.

Selfie with our trusted HIPAA attorney and friend, Roger Cohen (Life Sciences Partner, Goodwin)

Meeting James Coates (SVP Marketing, TimeDoc Health) IRL

The rest of the day is a blur. Shaking hands, hunting down customers (there were a lot of them), doing my best to add new connections on LinkedIn, engage with them, and remember to follow up afterwards. 

Still managed to get another blog post out that day as well.

Wednesday. Back in SF.  Went to the office to compose my thoughts and compile a Google Sheet of my new connections for follow ups.

Not feeling so great, only worked a half day. Must be the sleep I haven't been getting.

Thursday. Wrong. I have Covid. Can't even process three sentences at a time. 

No one else on the team got it. Go figure. 

Game over (for now). Time to rest up. 

A week in the life of a startup CEO.