The First Issue of Our Newsletter is Live!
We are so excited to have the first issue of our new independent newsletter live, and you can subscribe here. If you think this is awesome, I hope you will help us spread the word by forwarding the email, Tweeting, etc. For now, we are going to consume feeds throughout the week and recap the best content coming from startup operators and investors through the week, and send it out to you on Saturday mornings.
If you’d like to recommend a piece of content, suggest a job post, or sponsor the newsletter please get in touch with us at firstname.lastname@example.org
Also, a big thank you to long time startup friend Tony Blank from SendGrid for generously offering to sponsor our email sending so we could get this entirely bootstrapped effort out the door without breaking the bank!
Danielle & Kevin’s Startup Newsletter with No Name – #1
For those who subscribed awhile back, this is the DanielleMorrill.com newsletter, where my husband Kevin and I are exploring a new weekly (and maybe someday daily) newsletter about startups, investing, our new life in Denver after selling Mattermark, and exploring how to bootstrap a new business around this content.Â â€” Danielle
Iâ€™m excited to write this newsletter alongside Danielle.Â In orderÂ to find, organize, understand the best writing on startups across the web I amÂ using machine learningÂ to find hidden gems that could have been easily missed. Beyond startups, I have many intellectual interests including the history of invention and philosophy. I’m exploring how this technology could generate other topical newsletters.Â â€” Kevin
From the Operators
Adora Cheung ofÂ Y CombinatorinterviewsÂ Ooshma GargÂ ofÂ GobbleÂ about the evolution of her prepared meal kit delivery companyÂ andÂ endurance through The Struggle
Mike Maser of Big Sky Health shares his journey from user to CEO of Zero Fasting App, which was originally created by serial entrepreneur Kevin Rose in â€œSaved by Zero â€” Surviving Cancer, Discovering Fasting, and Turning It Into My Next Career Journey Â Retired serial startup founder, author, professor and investors
Steve Blank comments on the return of a late 90s startup trend: high profile founders raising huge amounts (like, 3 commas huge) of capital with nary a product in sight in â€œIs the Lean Startup Dead?â€ Â
Harj Taggar of Triplebyte provides a hands on guide with actionable advice for â€œConvincing Engineers to Join Your Teamâ€ Â
Kevin is a moderator for 30 companies in Y Combinatorâ€™s Startup School, and this weekâ€™s theme is Product Market Fit with two helpful founder accounts:
* Peter Reinhardt tells the story of Finding Product Market Fit at Segment
* David Rusenko tells theÂ story of Weeblyâ€™s long fight to capture product market fit
From the Investors
Congratulations to Angela Tran Kingyens on her promotion to General Partner at Version One Ventures. Angela joined the firm 5 years ago, and we are proud to have worked with her through that entire time as portfolio founders at Mattermark. She is one of the few investors we now who can make an API request, and we canâ€™t wait to see what she invests in next!
Arlan Hamilton of Backstage Capital launched the firmâ€™s startup accelerator program this week, and offered commentary on claims that comments to the press were â€œcalling out other acceleratorsâ€ for their lack of diversity, in a tweetstorm on Thursday evening.
Peter BrackÂ introducesÂ his new venture firm HypothesisÂ on the belief that great companies can and should be built everywhere in “Hypothesis: The Next Wave of Transformative Companies Will Come From Outside of Silicon Valley”
Lisa SuennenÂ formerly of GE Ventures reflects on the wisdom of Winnie the Pooh as she says goodbye to her role at the corporate venture firm in “Whatâ€™s Next?! A Plan in Progress” Â Venture Capitalist
Brian Laung Aoaeh shares his story of deciding to disband KEC Ventures in “#ProofPoints: An Ending + A Beginning”
Semil Shah of Haystack opens up a conversation about whether VC need to “go all in” to demonstrate their commitment in “Conviction, Diversification, and Portfolio Construction”
Rob Go of NextView Ventures ends a busy summer with a thoughtful post outlining the core beliefs of his firm in â€The NextView Ventures Manifestoâ€
Startup Jobs to Check Out
FlexPort is revolutionizing global trade and disrupting an industry that touches every person on earth. The company is based in San Francisco, and theyâ€™re hiring several Software Engineers to solve complex challenges. Â
Treasury Prime is transforming banking. The company is based in San Francisco, and they are hiring engineersÂ to build modern banking infrastructure for 21st Century. Â
Enzyme is building FDA compliance and quality systems as a service. The company is based in San Francisco, and they areÂ hiring a Director of Engineering. Â * we are angel investors in this company
This Week’s Book Pick
â€œScale: The Universal Laws of Life, Growth, and Death in Organisms, Cities, and Companiesâ€ by Geoffrey West
Ready to geek out on power laws, fractals, and connections between the natural world and the man-made? This book took our curiosity soaring several times and is a relevant read for those navigating the growing pains of a startup going from a two person team to 200, or VC firm going from 2 partners and $25M to a second or third fund 10x that size.
Thank you so much for reading our very first independent issue of this newsletter. We still have a lot to figure out, including the name, sections, business model(s), and more. Your feedback is welcome, and will reach both of us when you reply to this email or send a message to email@example.com Â Much Love, Danielle & Kevin
Commenting Like Itâ€™s 2009
Iâ€™ve been going back and forth on how, when, why, and how much to use social media. Part of my struggle is that I moved away from San Francisco in December after 10 years (most of my adult life), so I donâ€™t want to lose touch with my friends and sometimes I get really lonely. Part of my struggle is that I do get a lot out of engaging with intelligent, interesting, thought provoking people and I donâ€™t want to miss that.
To satisfy this need, and to explore something I remember loving, I started commenting on the blogs Iâ€™m reading and enjoying. I am such a blog lurker, powering through 50-100 posts per day without saying a word. I remember how much I used to love commenting on blogs and meeting new readers and friends that way. Iâ€™ve been blogging since the days of mydiary.net, Livejournal, Xanga etc. and in those ~20 years since the late 90s it feels like commenting has died out a bit. Notoriously, people will give the advice â€œdonâ€™t read the comment sectionâ€ to new bloggers. I was never able to follow that advice. Who am I writing for, if not the readers? How wonderful to get to engage, and tools like Disqus provide excellent moderating powers.
On the other hand, there is a lot of content (especially on Twitter) that I just find myself totally distracted by where reading the threads of mentions and replies can send my mood into a tailspin. I emerge hours later wondering where my morning went! I am a big believer that one needs to be very thoughtful about what they let into their mind, because it keeps working on you in a subconscious way. I started by deleting most of my old tweets so there wasnâ€™t such constant stream of spamming of likes and comments picking up old threads out of context. That has been great. I feel like a traitor to the original ethos of Twitter, which was to not delete any tweets (not even for typos!) and I am sad to have lost some of the collaborative â€œperformance artâ€ that was so fun to create. I also have begun to actually block people, which also feels against the original community ethos of engagement but truly makes a huge difference in the experience. Twitter is the closest to a true addiction for me, I open it when I have a moment of standing in front of the mental refrigerator between tasks. I am playing with different approaches to training this out of myself and Iâ€™ve tried several strategies including deleting the app from my phone or limiting myself to only reading while I am exercising, and only posting on Sundays.
Facebook is easier to quit. I donâ€™t care so much about the data tracking, perhaps because the ad form factor on FB is so crappy there is really never a risk of me buying anything. I rarely see weird political shit and when I went to download my profile of how Facebooks â€œseesâ€ me I discovered it was somehow grouping me in the 65+ year old man category. LOL! Fine by me, my feed is mellow. As to people, curating my friends into real friends and acquaintances has been helpful. My default post mode excludes my acquaintances, which removes a lot of the awkward commentary. At this point, I prefer Facebook for the features that help with handling life coordination like EVENTS. I think a lot of the stuff Iâ€™d like to get done inside a personal CRM is semi-possible with Facebook. I donâ€™t have FB on my phone, just my iPad, which means it is not a time killer for me.Â
Instagram is my favorite place to be when I have a few minutes free because it is beautiful, and I actually see ads for products I want and buy. I recently made my account private, but I have maybe ~150 people who are regularly looking at my story and ~20 people who are giving me likes regularly. These numbers feel much more reasonable and closer to real life and real friends than my 72,000 followers on Twitter. I donâ€™t have notifications on for Instagram, which is good because it keeps me from getting addicted to the little dopamine droplets. Instagram feels like a place where Facebook can actually get me to do things: I have bought shoes, bikinis, and household decor because of ads on Facebook and have a collection called â€œBuyâ€ that I actively curate so I will have ideas for gifts all the time. I feel like the ads there are really tailored for me, not crap.
In the spirit of commenting Iâ€™d love to hear your thoughts in the comments here. How are you engaging with the writers, thinkers, bloggers and other sources of good and useful stimulation online these days?
Taking a Break from BUMMER (Twitter, Facebook, and Instagram)
A friend recommended I read â€œTen Arguments for Deleting Your Social Media Accounts Right Nowâ€ and while I was initially turned off by the title (see what they did there!) I read it. I donâ€™t know about boycotting anything, but on a personal level it dovetailed nicely with a journal entry I had written last week, reflecting on how much my ego used to feed off of media hits and the dopamine hits I got from â€œengagementâ€ (manipulation?) of a large Twitter following. Was I a narcissist? I still donâ€™t know, but what I do know is I dislike who I am when Iâ€™m on Twitter and to a lesser extent on Facebook.
It also explores a lot of feelings Iâ€™ve experienced regarding my use of social media, but had a hard time giving a name before. This goes back to the times of bulletin boards, and many of the much older platforms… but now we are beyond the earlier adopter stage, and the vibe has changed.
I like to test these things out, and Iâ€™ve been living a little differently since I went on sabbatical in mid-May. Why not? Would these things be deeply missed, or simply go the way of my accounts on MyDiary.net, Livejournal, MySpace, Flickr, Photobucket, Xanga, Svbtle, and so many more? Barely missed, hard to even remember the names and proper spellings required to construct that sentence.
Earlier this week, I deleted Facebook and Twitter mobile apps from all my mobile and tablet devices. The withdrawal has come in waves, and I have started keeping a journal to jot down random thoughts I would have tweeeted in the past. Often, these are turning into 500-1,000 word journal entries.
Then, yesterday I archived and deleted all my tweets. Itâ€™s been 24 hours, and I donâ€™t think anyone has really noticed. Iâ€™ve been liking some friendâ€™s posts from the web interface when I log in to see what the reaction is to my empty account (nothing). Iâ€™m pretty sure hitting publish on this blog post is going to auto-tweet, and I canâ€™t figure out where the heck I set that up so Iâ€™ll just have to go an manually delete it.
Today, I took what for me will be the hardest step yet, and removed the Instagram mobile app. Itâ€™s the one I am the most addicted too, and I had rationalizeed it was not a source of low self-esteem or time suck, and that I didnâ€™t actually get many ads there. Then a pair of His and Hers slippers for my husband and I arrived in mail that I knew I had found on Instagram through an ad. Then I saw the same ad again today (and told Instagram I was seeing it too frequently). Then I wasted 45 minutes looking at my feed of Instagram models and vacation lifestyle accounts. Ok… maybe this is actually more of a problem than I thought.
Iâ€™m not ready to delete my accounts outright. I have some big questions about identity on the Internet, and I fear someone would take my username and then manipulate people who thought it was me. I also might come to regret this whole experiment, or decide to just go back to using these services like normal. I donâ€™t know what will happen yet. I am also still trying to figure out what I am going to do with the accounts for my dog Emo, who is a source of sweetness and happiness to a couple hundred people and one of the best things in my life. TBD.
I emailed my immediate family and Kevinâ€™s immediate family to let them know I was taking a break from social media, so not to worry if they didnâ€™t see posts from me and to reach out for 1-on-1 communication by phone, text, or email.
Of all the arguments in â€œ10 Argumentsâ€, the most compelling is the last one â€” about religion, specifically AI heaven or the singularity. In our race to fulfill this fantasy, weâ€™ve built a hierarchy that places machines above humans and formed a religion that evades the responsibility of consciousness. What we build is a choice, and the point of the book is to advocate for different choices. I am certainly pondering this as I contemplate what I build next, given I canâ€™t unsee what the author has made clear.
â€œAI has become a fiction that has overtaken its authors. AI is a fantasy, nothing but a story we tell about our code. It is also a cover for sloppy engineering. Making a supposed AI program that customizes a feed is less work than creating a great user interface that allows users to probe and improve what they see on their own termsâ€”and that is so because AI has no objective criteria for success.â€
As someone evaluating companies for angel investment who claim to be building â€œAIâ€ and turn out to have very basic technology that trains and classifies on some set of UGC I see this fiction re-written in decks daily. As someone who just spent 5 years leading a company that leveraged machine learning in a meaningful, and sometimes meaningless, way â€” this rings so true. I am wearing an old Mattermark shirt that says, â€œbuilding the basilisk since 2013â€ and the irony is not lost on me.
In dreams begin responsibilities.
Prototyping a Personal CRM: Lessons Learned So Far
I just discovered this week that I didnâ€™t have product/market fit with my own prototype. How do I know? After using it every day from April 22nd – June 29th I just randomly stopped for over 2 weeks. But letâ€™s backtrack a bit, what is this prototype anyway? Itâ€™s a series of Google Docs and Google Sheets chronicling my backlog of personal life crap, recurring stuff like the dentist and habits Iâ€™m trying to establish, trip planning (often shared with others), a long list of dates to plan with Kevin, family members with big stuff going on and reminders to send notes or flowers, and a jumble of other personal activities, aspirations and ideas that come up throughout any given day of stuff Iâ€™d like to do if I were a more organized woman, wife, sister, daughter, businesswoman, human being. It has some goals for each month across the top, mostly to do with budget adherence and planning ahead for big stuff like our 11th wedding anniversary next month. Itâ€™s actually too personal for me to share (!!) unlike Facebook. Itâ€™s got a running list of birthdays, and I started transcribing fitness goals that I normally track in Apple Health apps.
Basically, the data entry of my own prototype started to kick my ass. It is looking more like a personal assistant to guide me through my days, like Google Assistant perhaps (I havenâ€™t used it) without any UI. The best part about using it is looking out into the future and thinking ahead to things I want to plan, organize, prioritize etc. and feeling a sense of greater foresight and control in my life. I did this frequently for my business, but applying it to my personal life is new. Since Iâ€™m on sabbatical and have a dearth of hours for personal life stuff, this might be a bit of an artificial environment.
And yet with all this, I stopped using it for 2.5 weeks. If I wasnâ€™t working on it as a gentle prototyping activity for one of my more compelling startup ideas I might not have even come back to it.
In part, I was pushed away from using it as my life became less structured with my break and I started to settle into a less planned existence. Yay! But the other side of it is that it became too much work, and weâ€™ve all heard this complaint about CRMs before. The sales manager asked the reps why theyâ€™re not updating the records, taking notes, logging calls, and really only putting in closed won deals and the answer is usually â€œI donâ€™t have timeâ€ or â€œthere are too many fields to fill in that donâ€™t mean anything to meâ€ or some other flavor.
My mind jumps from here to integrations. If this wasnâ€™t a Google Doc could it be software with all the integrations needed to automatically generate the same thing I have wanted (basically a bulleted day planner connected to goals and deeper context than one usually puts into calendar events)? So Iâ€™m back on the wagon, and using some crazy color coding to highlight the integration types that would be required. This is leading me down the path toward what RelateIQ was great at: extracting valuable information needed to update the CRM from email. What I really need is integration with email, text messages, Facebook, Twitter, etc… and this starts me thinking about how to leverage a unified inbox like Front to do the heavy lifting. A quick search reveals they do have an APIÂ https://frontapp.com/api
Building that inbox from scratch is really not the point of this personal CRM, so I wonder if I could bootstrap something simple… but I see my thoughts are running toward software implementation. Itâ€™s not time for that yet… I need to prove out the value of the integrations with my duct tap and bubble gum version first.
I wonâ€™t lie, itâ€™s fun building something just for myself. Many, many, MANY people have followed up from my tweets asking if I have something they can use yet. Iâ€™m really sorry, I donâ€™t and even sharing with you what I have is just too personal. Which is the true victory so far… I am really using this for my real life, but only when I remember to log in.
Request for Startup: Subscription Car Wash a la WeWork
Here in Denver I subscribe to a monthly car wash membership for my black SUV which allows me to bring the car in as many days as I want for the same price. Since I have a black car I use this a lot, especially in the winter months when the car is constantly getting splashed with dirty slush. I rent my car out on Turo, so year round I use this service quite a bit (after each transaction) and also let my passengers know they are welcome to take the car in anytime they like. Youâ€™d be surprised by how many do! Denver people are the nicest.
Iâ€™m fascinated with subscription business models (I just got an unlimited monthly subscription for my eyelash extension fills!) and this one seems ripe for a WeWork-style startup to score real-estate and create a consistent U.S.-wide (or even global) car wash experience BRAND. They could buy up existing car washes. They could partner with them and provide McDonaldâ€™s-style â€œuniversityâ€ to help franchise owners maximize the value of their property with best practices. They could use collective bargaining to get better deals on equipment, supplies, etc.
Does this startup exist? Are you building it? How would you start?
Update: Thanks to Sachin Agarwal for pointing me to Spiffy, who recently raised $8 million in Series A financing
Iâ€™m Taking Self-Funded â€œSabbaticalâ€ for the Rest of 2018
In this podcast interview on â€œFounders Talkâ€ with Adam Stacoviak we talk about the decision to sell my startupÂ Mattermark, the process of getting the deal done, managing psychology and explore the many choices along the way.
Listen to the full interview here or download and listen on iTunes
If youâ€™ve been following along on social media, you might have heard me say â€œIâ€™m on sabbaticalâ€ lately. Itâ€™s true, Iâ€™m no longer an employee anywhere and this break is self-funded (some folks pointed out saying sabbatical sounds like something that Iâ€™d negotiated as part of the acquisition), so Iâ€™m not sure what to call it. Yesterday was the start of my 9th week of this new phase, and Iâ€™m not planning to work for the rest of 2018 (more on what I am up to coming in a future post).
This interview with Adam is my first deep dive into the process of selling Mattermark, and I hope it will be helpful to other founders who might find themselves in similar circumstances. Iâ€™ve tried to present the story with as little spin as possible, both on the positive side and also on the negative side. The truth is that Iâ€™m not devastated by this outcome and it is certainly still much better than that typical startup result (a total shutdown without any sale at all). I am proud to have â€œlanded the planeâ€ and Iâ€™m sure I was not the perfect CEO, but believe I have acted with high integrity at all times and generosity wherever it was possible. There is certainly a grieving process as I shed the roles, rituals and perks of being a startup founder and CEO but I am starting to see things in a more balanced light.
The coverage of Mattermarkâ€™s acquisition in December certainly wasnâ€™t the kind of ending Iâ€™d hoped for after an exhausting process, but by that point so many other things had happened that it was really just another thing to survive. I was living life day-to-day, just waking up and putting one foot in front of the other, and I needed a break from the hyper-transparent life Iâ€™ve been leading on the Internet. Instead of the typical crappy acquisition fluff post TechCrunch tends to do, our deal details were leaked and the media angle was primarily a criticism of my toneÂ in an email to common shareholders (I said â€œI have great news!â€ before telling common holders theyâ€™d been wiped out â€” not my best choice ever, but also not deserving of so much of the Internetâ€™s asymmetrical ire in the Twitter outrage machine). It sucked.
When the story broke, I was so sleep deprived standing in my furniture-less rental house in Denver with the deal less than 24 hours from closing I could barely stand. Friends had a variety of pieces of advice, â€œYou have to respond and defend your reputation! Your fans deserve to know the truth! Perhaps a mea culpa?â€
After my head stopped spinning I puked in the sink, rinsed it down, and texted my board for advice. â€œTime to get off the Internetâ€ they said. I focused my last dregs of energy on completing the deal (it closed the next day) and did just that. Iâ€™m proud of that, I knew I was strong but this was definitely the most I had been tested since some of the most stressful moments at Twilio… and the stakes were much higher.
I resumed work 3 weeks later and in total spent 6 months not only transitioning Mattermark but also running the Product organization at FullContact as a member of the exec team, professionalizing the Product org, establishing process and training, eliciting input from across the organization and establishing a roadmap aligned with the companyâ€™s strategy. Iâ€™m proud of the work I did there and truly believe I left things better than I found them. I loved getting to know my team and weâ€™ve formed friendships that will last a long time, and we never would have been able to accomplish so much in just two quarters without their commitment and tireless engagement. Mattermark has been successfully transitioned, and continues to operate as a revenue-generating part of the FullContact product portfolio.
Now Iâ€™m a free agent.
Iâ€™d love to engage with readers who Â been through acquisitions, life and career resets, and other major transitions as I figure out what I would most like to do next. Start a company? Join a startup? Join a larger company? Switch industries? Become a full-time investor? Become a full time writer? Itâ€™s all on the table.
P.S. I am still actively angel investing in startups and funds, and you can learn more about how we are supporting female founders at XFactor Ventures. As reported by Forbes last month, we have big plans to raise a larger second fund.
Thank You Mattermark Daily Readers, Contributors and Editors
After many years, the newsletter that was the genesis of my former startup, Mattermark Daily is sending its final missive today. It was such a pleasure to read the Internet and scour for posts to share 4 days a week with more than 100K readers, 60K of whom opened the Mattermark Daily each day at the peak of her awesomeness.
I started the Daily and wrote it for the first 18 months, and then it was the labor of love and dedicated efforts of many subsequent Editors in Chief who made it fantastic (and also made sure it published on schedule!). My deepest gratitude goes to Kevin Morrill, Andy Sparks, Sam DeBrule, Wade Vaughn, Nick Frost, Alex Wilhelm, Jonathan Kressaty, and Ashley Lozito for scrolling through thousands of articles to bring readers the best hand curated startup reading over the years. I am especially proud of adherence to our editorial standards, never-ending search to find more female authors, occasional wit, inside jokes, and exposure of new and up-and-coming startup blogs.
Below are a selection of links covering the Mattermark Daily, a wonderful product I am proud to have built and that brought happiness to many people. R.I.P.
- Ryan Hoover: Blog First Startups
- ValueWalk: Hereâ€™s What the Most Iconic Tech Investors Read Each Morning
- Fast Company: 5 Successful Startups That Started as Blogs
- Next View Ventures: Inside the Mattermark Daily, Principles & Process
- Teamwork.com: How to Turn Your Boring Newsletter into a Customer Acquisition Machine
Thank you to everyone who tweeted, blog commented, Hacker News commented, Quora posted, and otherwise spread the Mattermark Daily organically through word of mouth.
If you are looking for something new to read, I am sorry to tell you I am not starting another newsletter (the editorial schedule is grueling â€” much respect!) but Product Hunt does have 6 alternatives to the Mattermark Daily listed, and it would be awesome if you submitted more to them!
Did I miss a great press clip about the Mattermark Daily? Let me know in the comments so I can save it in the archive. This will be fun to look back on in 5, 10, 25 years 🙂
Reading List for Making Relationships Better
At FullContact, our vision is to “make relationships better” and I’ve spent the last few months wrapping my head around what this *really* means in the context of profiles of people and linkages between their different online identities. The fundamental idea behind this vision is that more data is better for decision-making, and that customers can craft advertising. marketing, and product experiences that are deeply human when they make decisions about what to say, do, offer, etc. with the full richness of understanding a person.
This is a significant departure from my day-to-day obsession with companies, financing events, mergers and acquisitions. To help me explore this head space I’ve embarked on a reading syllabus that encompasses neurobiology, psychology, sexual education, parenting, and much more. Here’s what I’ve been reading lately:
- The Science of Trust: Emotional Attunement for Couples by John M. Gottman
- Achtung Baby: An American Mom of the German Art of Raising Self-Reliant Children by Sara Zaske
- Your Brain on Love: The Neurobiology of Healthy Relationships by Stan Tatkin
- The Seven Principles for Making Marriage Work: A Practical Guide by John M. Gottman
- How to Stop Time by Matt Haig
- How Dogs Love Us: A Neuroscientist and His Adopted Dog Decode the Canine Brain by Gregory Berns
- NeuroTribes: The Legacy of Autism and the Future of Neurodiversity by Steve Silberman
- How to Talk So Kids Will Listen & Listen So Kids Will Talk by Adele Faber & Elaine Mazlish
- Wired for Love by Stan Tatkin
- The Body Keeps the Score: Brain, Mind, and Body in the Healing of Trauma by Bessel van der Kolk
- Come As You Are: The Surprising New Science That Will Transform Your Sex Life by Emily Nagoski
- How to Create A Mind: The Secret of Human Thought Revealed by Ray Kurzweil
- The Neurobiology of ‘We’: How Relationships, the Mind, and the Brain Interact to Shape Who We Are by Daniel J. Siegel MD
“This Storm Is You” and Other Thoughts After a Year in M&A Limbo
I spent the last 9 months working on selling my previous startup, Mattermark, and now it’s finally done. This blog is more than 10 years old, and I’ve been blogging for nearly 20 years now… so the break from writing and sharing my life has been strange, but good. Now I’m ready to get back to it, and I find myself transformed by life (this is always happening, but it’s often so gradual you don’t notice it) and having a hard time recognizing my old voice, my old “face” in the digital sense. Writing here again, logging into the WordPress console and skimming hundreds of stubbed out potential posts I haven’t touched in quite awhile, is like looking into a mirror after spending a year shipwrecked.
I love Japanese author Haruki Murakami’s construction of surreal metaphors for transformation, and in many of his books he builds up real storms toÂ unleash a metaphor of lasting change in the course of his character’s lives and selves. From his novel Kafka on the Shore, this passage has stuck with me and is a way of conveying what I know about what has happened to me in the past year:
“Sometimes fate is like a small sandstorm that keeps changing directions. You change direction but the sandstorm chases you. You turn again, but the storm adjusts. Over and over you play this out, like some ominous dance with death just before dawn. Why? Because this storm isnâ€™t something that blew in from far away, something that has nothing to do with you. This storm is you. Something inside of you. So all you can do is give in to it, step right inside the storm, closing your eyes and plugging up your ears so the sand doesnâ€™t get in, and walk through it, step by step. Thereâ€™s no sun there, no moon, no direction, no sense of time. Just fine white sand swirling up into the sky like pulverized bones. Thatâ€™s the kind of sandstorm you need to imagine.
And you really will have to make it through that violent, metaphysical, symbolic storm. No matter how metaphysical or symbolic it might be, make no mistake about it: it will cut through flesh like a thousand razor blades. People will bleed there, and you will bleed too. Hot, red blood. Youâ€™ll catch that blood in your hands, your own blood and the blood of others.
And once the storm is over you wonâ€™t remember how you made it through, how you managed to survive. You wonâ€™t even be sure, in fact, whether the storm is really over. But one thing is certain. When you come out of the storm you wonâ€™t be the same person who walked in. Thatâ€™s what this stormâ€™s all about.â€
I could write a whole book about selling the company and still not convey what is captured in this quote. There are the logistical details on doing a M&A deal, but the more interesting part to me is the psychological journey of spending years of one’s life creating something, and then realizing it is time to let it go.
In 2017 faced the true finitude of my own life, of my time here to do the things I find personally meaningful. I read everything I could get my hands on to help me make good decisions about what matters, and while I love philosophy there is no single guidebook for effectively bargaining with our finite time on Earth. There is quite a bit of startup mythology to lean on, but when I had been recommended to read The Hard Thing About Hard Things for the tenth time I realized no one really knows what they’re doing, and there is more to it than just how to “do a startup”.
2017 was about taking control of my story, and I just kept re-learning something I had already figured out in January 2016, when I wrote Overcoming the Tyranny of â€œShouldâ€:
“There are a lot of articles telling us what we should do to be good, often formulated to demonstrate how to be more like whoever the hero CEO is. Wake up early. Time block your calendar. Raise now. Get that big valuation so it will be easier to recruit. Everywhere I turn on Medium someone has advice for what I should do, and I tell myself to listen because I want to be open to feedback and I want to learn. But sometimes when I am able to quiet that story down, I catch myself listening because it is just so much easier to have someone else figure out what I should do.
â€œIâ€™m tired. Could you bargain with fate for me please? Thanks.â€
What I’d already learned, but had a hard time holding onto, is that you can’t delegate these big decisions to someone else’s checklist of “10 Ways to Know It’s Time to Sell Your Startup”.
What I’m Doing Now
While I dearly miss my friends and my City I’ve loved spending time outside the Bay Area, because it is giving me the mental space to quiet a lot of the noise I was letting in before.
We’ve rented a house in Denver and been here almost 3 months already, we have a 6 month old black Lab puppy named ‘Emo’ who loves to nap and play, we’re working on what our marriage can be now that we’re not running a business together, and also taking much more time for our health and fitness.
Instead of taking a year off, as I had originally planned to do to write a book, I’m working full-time for a mid-stage startup where I am running Product without having to simultaneously run the entire company (which is what I was doing before). I’m reading at a pace of 1-2 books per week, and you can check out my library on my Goodreads profile.
I hope to keep writing, both on this blog and possibly to restart that book project I mentioned, but I’m not ready to commit to publishing every day. There’s just so much living to do, and so much more time to do it now that I am forcing myself to work normal 40-50 hour weeks! I have 1,000 square feet of finished basement to set up as an art studio, another 20 pounds to lose, a bunch of tickets to concerts (including Emo Nite, Sam Smith, and Odeza!) and several trips planned in the coming months including Disneyland, the French Riviera, and Kevin’s 40th birthday extravaganza in Vegas.
I’d love for you to follow along with those adventures on my Instagram.
To my friends, family, team, and others reading this who showed me love and support through this process in 2017 and throughout this crazy startup life — thank you so much for everything, I love you too. I’m ready to move on now, and start creating things again and sharing my life on the Internet like I always have done. I’m also so ready to hang out again, sorry I’ve been a hermit!
Checking On Predictions & Fantasy VC Portfolios
On June 8th, 2017 I made a list of 20 companies that looked ripe for Series A… it has been nearly 4 months and I just checked to see how my predictions are going. 1 out of the 20 has announced their Series A so far:Â ClearMetalÂ announced a $9M Series A fromÂ Innovation Endeavors and Prelude Ventures.
I love to publish picks and then see what happens, and back in February 2014 I shared my fantasy VC portfolioÂ of 7 companies, and then updated it in February 2015Â showing a nearly 9.1x* increase in total funding (*excluding the Uber pick) from my initial selection. This group is now at 14x* total funding since my initial selection date, with 2 exits.
Ugh, nothing like embedding a Google Docs spreadsheet to make me wish I was still working on GitSheet!
I’ve made enough different prediction posts at this point, not to mention actual investments, where it seems like a good idea to start wrangling them all into one place. Eventually, one spreadsheet. But for now, let’s continue to time travel…
In June 2013 I flagged 10 Pre Series A Companies to Watch in New York, which included my initial call for Digital Ocean (who had not yet announced any outside funding). Of these companies, 3 raised a Series A, 3 were acquired, 2 shut down, and 2 are still going strong.
To be continued… there are definitely more of these posts hanging around.