Life Update: April 2021

“The muse may have more than one job for us over our lifetime.”
—Steven Pressfield, The War of Art, (p. 95)

Last week, we announced that paperback and hardcover copies of my book, The Holloway Guide to Raising Venture Capital, are available on Amazon here.

It was an exciting day for all the obvious reasons. Holding a physical copy of something I worked on for years, the thing looks and feels beautiful, and the beaming pride from Mom and Dad didn't hurt.

But it was also a strange, confusing day. We set out to write this book for two reasons:

  1. We were starting a book publishing company, and we wanted to learn what it took to write, edit, and publish a book.
  2. We felt like all the other "how to raise VC" books were written by VCs, and I wanted to take everything I learned outside of books and put it in a book.

I think we accomplished both of those goals. But we published the digital version almost a year and a half ago. And since then, I've kind of … moved on. I'm no longer the CEO at Holloway. On top of that, through writing the book, I came to the conclusion that the allure of venture capital and all the trimmings of "startups," lure (intentionally or unintentionally—it's probably a mix) bright-eyed founders into a model for business building that puts people on a treadmill toward unlikely success.

When people ask me today how to raise venture capital, I respond, "Are you sure you need to?"

In the end, yesterday was strange because I can't shake the feeling that I wrote a book on something I'm not that interested in being an expert on anymore.

What a sales pitch, right?

I'm still very proud of the book. Thanks to Rachel Jepsen's nudging, we addressed the issue of whether to raise venture capital or not in a chapter of the book. I think the book will continue to be very helpful to a ton of entrepreneurs.

Short Updates

  • Moving to Denver: On April 29th, movers will come and pack Kate and I up. We're moving to Denver. It's a fun homecoming of sorts. I was born in Denver and lived there until I was eleven. My family has moved on, but I'm excited to begin a new chapter with Kate there. If you know good people, good restaurants, bars, things to do, please reply and share!
  • Leaving San Francisco: Leaving during a pandemic is strange. If you know me well, you know that I love to throw a good party. Over the years in San Francisco, I've hosted Ocean Beach bonfires that got so big the police had to break them up, monthly backyard BBQs with the Rahmans, and many glorious days in Dolores Park. But this year: no parties. I feel a bit like I'm sneaking out the back door. My best friends know I'm leaving, but I haven't been able to bear telling the owners of my local pub, Shotwell's. For some reason, I don't want to admit I'm leaving.
  • David Whyte: Thanks to Jonny Miller, I found myself 20 minutes before a coaching session with a client crying in my office listening to David Whyte talking with Sam Harris about friendship. I chalk it up to leaving San Francisco and reflecting on the amazing friendships I've gained and maintained here, particularly Samiur Rahman and the wonderful Carrie Phillips (who moved here with me almost nine years ago to start a company!). After that, I finally finished Crossing the Unknown Sea: Work as a Pilgrimage of Identity, in which my favorite line was something along the lines of "Don't fuck with the poet!" You can be sure I'll be reading more David Whyte in the coming months.  
  • Between: For the new folks, Between is a podcast I'm working on where I'll be interviewing people about the relationships behind companies and products we love. The wonderful Hamish Smyth recently shared his first cut at the art direction (see here), and I'm working on a "trailer" of sorts (see here). I'm hoping to have first episodes out this summer.
  • Reading: You can always follow along with my reading here (under the books heading). This year, my reading skews heavily toward books on coaching, as I train as a coach. But these books are fascinating, and every time I open one of these books I know I'm going to be a different person at the end. I now read for about 1-2 hours every morning, and the feeling of being a student because I want to be not because I'm supposed to be is extraordinarily liberating.
  • Ask Jerry: A month or two ago, I decided to move on from writing Ask Jerry. After some reflection, I realized I wasn't really writing as much as I was editing Jerry. And that's not what I wanted to do. I also had to reflect on my own desire to be associated with someone I admired as I made a career switch. I'm glad I worked on it while I did, but some things just need to be experiments.
  • Editing: Rachel Jepsen edits almost everything I write. Except she didn't edit this. Because she's working on editing a big piece on coaching I'm working on, and I wanted to get this sucker out there. So if there are typos, it's on me.

How You Can Help

  • If you or anyone you know are interested in working with me as a coach. Reply to this email and let me know so we can set up some time!
  • Buy a copy of my book here!
  • How was this email? What did you like? What should I keep doing? What should I stop doing?

Looking forward to what’s next,


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