I’m feeling ready to get back in the swing of blogging, and generally dialoguing with people around the world about ideas, products, and (eventually) another startup. In order to do that, I feel like a little recap of 2018 is in order. Overall, it’s hard to simplify it down to an “awesome” or “challenging” year because it was both, and much more. We moved to Denver in December 2017 coinciding with the sale of Mattermark to FullContact and spent Q1 just settling in and working a lot. After 10 years of apartment life in which we moved 8 times we didn’t have much stuff, and in our new 3-story 3-bedroom townhouse we were awash in empty square footage. Our puppy loved it!

Initially I thought I would take it a bit easier on myself after the M&A slog, and we had even discussed 3 months off before stepping into the full-time gig, but my role ended up being much more central to the company operations as I stepped into the shoes of a departed VP Product. Despite how it was reported in the news, Mattermark was very much operating and there was a long integration checklist to complete.  set myself back into the rhythm of endurance, Navigating a couple legacy product shutdowns, GDPR, and shoring up process around roadmap and requirements writing was beyond a full-time gig but thanks to the incredible PM team and the relationships we formed, it happened and for the first time since early 2012 I was back on the exec team of a startup rather than running it, and had hit all my OKRs. That felt great.

At the end of Q1 I also started to work through my list of neglected relationships with a trip to Disneyland with Kevin’s family, including my two adorable nephews and spunky niece, and then headed to Austin to visit my sister and meet her newborn baby son (my 3rd nephew!) for the first time.

As Q2 began, I prioritized re-connecting with the women in my life, friendships that have been incredibly durable and sustaining the face of my crazy founder life. In early April I hosted the first partner meeting for XFactor Venures at my house in Denver and then headed out on a two-week birthday trip, planned over 6 months in advance, to cook in Julia Child’s home in the South of France and explore romantic spots on the French Riviera with my husband (and former cofounder/CTO). When I returned to Colorado I was tan, relaxed, and ready to make the leap into the unknown. My last day at FullContact was May 4th, and we enjoyed some Frozen themed cupcakes to say goodbye to the working world for awhile.

After ~20 years of uninterrupted work (with over 10 of those years in startups), I embraced the freedom to do whatever and be whoever I wanted with enthusiasm. I pierced my belly button, I got hair extensions and dyed them various shades of pink and rainbow, I spent 2-3 hours a day working out and walking my dog, I (gasp!) didn’t worry about who was looking at my social media posts of concerts, clubs, trips, and other fun. I also got a marriage counselor we love, bought myself a nice car, got a Peloton, lost 20 pounds, had more sex, slept like a baby, and lost track of time. For Kevin’s 40th birthday in May about 20 of our friends came to Vegas and we saw David Guetta perform an incredible set, honoring Avicii, from the best table in the club. We saw the final show in Paramore’s tour at the beautiful Red Rocks Amphitheater and watched Brendon Urie of Panic! at the Disco float above our heads playing a white baby grand piano for his stadium show at the Pepsi Center. I spent all of my 20s married, working hard, happily being a nerd… and I’d just turned 33. It was time to live a little, so I decided to live a LOT.

I addition to playing hard, I also worked quite a bit on my inner life and personal projects. I read over 100 books in 2018 spanning science fiction, popular fiction, philosophy, relationships, business, biographies, history, and many more titles that were queued up in the backlog. I took a significant step back from posting on Twitter and Facebook, and archived and deleted my entire history of tweets (I’ve since started tweeting again, but far far less). I outlined a handful of book ideas (2 fiction, 4 non) and began playing around more seriously with the personal CRM startup idea as well as a recruiting one, and also worked with my husband to curate a new newsletter of startup links called BuriedReads. I re-watched every single episode of Star Trek – The Next Generation with Kevin. I made a few angel investments and lead my 3rd deal for XFactor (not yet announced) and continued to deepen my interest and knowledge in aerospace and space exploration investing.

Also, life just kept happening… which meant weddings, visiting family in the Pacific Northwest, visits to Denver from friends (thank you so much, you helped with my homesickness immensely!), helping my sister with her family’s move back to our home town, health issues, managing day-to-day chores which I had pretty much forgotten how to do for myself while working (we had 2x-week help as married cofounders to eliminate any risk of tension, now we’re back down to every other week). The “errand paralysis” Anne Helen Petersen writes about in “How Millennials Became The Burnout Generation” began to ease up, just a little bit, as I started to build my days out of a series of more simple tasks like hanging the outdoor lights or assembling a piece of furniture (I still don’t have a Colorado driver’s license though).

While all this was going on, I was also quietly scouting around for things I might do next. A handful of venture capital firms had reached out immediately upon the sale of the company with partnership openings, and I explored those leads but the timing wasn’t right. A non-profit I’ve long wanted to improve reached out about an executive role on their team. Several of my angel portfolio companies let me know I’d be welcome to get more involved in day-to-day operations. Long-time friends who had started new companies offered challenging and deeply interesting roles. But I kept saying no, not yet, because nothing felt quite right…

Right now the life of an employee is still not something I yearn for. I’m a creator, an artist in my own way, and a maker of things and ideas. So far, this is what I have planned for 2019:

2019 curriculum is shaping up to be about how to build a good life 1) in a new city 2) making adult friends 3) maintaining long distance friendships 4) starting to lean into child free lifestyle as I turn 34 5) starting a new company outside the Bay Area

— Danielle Morrill (@DanielleMorrill) November 5, 2018

Happy New Year!

We are so excited to have the fourth issue of our new independent newsletter live, and you can subscribe here. 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 editor@daniellemorril.com

This is Kevin here writing this week. Danielle and I are back from Hawaii and adjusting to the Fall temperatures in Colorado. While we’re both taking time off between startups, it’s been noticeable how work pulls you back in even though you know you need a break. It’s been mostly me writing the past 2 weeks, so let me know if we’re doing a good job of keeping the quality bar high and the writing on point.

Engineering Newsletter Update: last week we previewed an upcoming newsletter focused on engineering content. Several of you are interested, and I’m working on v1, but want to make sure we can keep the quality high. Right now I’m culling together a list of 100+ feeds to pull the best content from, but we may need even more since great engineers tend to write infrequently. If you have anyone you know who’s written great posts in either startups or engineering, just reply to this email and let us know.

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From the Operators

Justin Jackson of Transistor.fm takes a sobering look at how long it will take to grow from $781 MRR to a living salary, and questions whether venture scale critics like Jason Fried of 37signals have misled bootstrapped founders in “Bootstrapper’s paradox”

Ammon Bartram and Harj Taggar of Triplebyte recently guided CTOs through the recruiting journey that is ahead of them. They took a comprehensive look at the recruiting ecosystem without overly selling their own service. You can learn from their hard earned lessons in “Building an Engineering Team”

Rand Fishkin of SparkToro points out that highly trafficked sites like Google, Facebook, Reddit, Instagram have become insular and shouldn’t be blindly relied upon to send you traffic in “The Powerhouses of the Internet Are Turning Hostile to Websites”

Amjad Masad of Repl.it gets a last minute YC interview, even after Rick Rolling the entire partnership in “Rejected Then Recruited: Our Journey into Y Combinator”

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From the Investors

Fred Wilson of Union Square Ventures celebrates 15 years of publishing his blog this week. He also sat down with Chris Dixon from a16z for a far reaching conversation on AI, crypto, and where we are in the history of the software industry. Easily one of the more thought provoking podcasts I listened to this week.

Hunter Walk of Homebrew cautions founders seeking bridge financing to expect the possibility of a flat round in “Second Seeds: The New Normal But Know This…”

Joanne Wilson of Gotham Gal Ventures recounts the an early career story of standing up to a bad manager in “Be Tough but Be Yourself”

Barry Eggers of Lightspeed Venture Partners shares his recipe for fund construction, sparing many first time VCs from mistakes that will come to haunt them when they raise fund II, in “VC Firms — How to Build an LP Base for the Long-term.”

Martin Casado of Andreessen Horowitz urges founders who are raising to preemptively calibrate their phase of growth for investors in “Aligning Startup Metrics with Stage of Maturity (Beyond Labels for Fundraising Rounds)”

Sammy Abdullah of Blossom Street Ventures outlines how to hire an investment banker for M&A, something too few founders proactively learn about, in “Negotiating with your investment banker”

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This Week’s Picks

Last week I recommended the Internet History Podcast, but I could tell from the click through count and my own hasty writing I didn’t do a good job describing it. When I first discovered this great work by Brian McCullough, I was glued to my earphones for days catching up on old episodes. It is an incredible trip down memory lane if you grew up in the 90s, and often gives you an “aha” moment as you see what was really going on behind the curtains. I hope you give it a listen if you haven’t already.

Connections by James Burke – anyone that works in tech and hasn’t read this book is in for a surprise. Each chapter of the book starts out at the dawn of civilization and follows a chain of an invention taking you all the way up to modern day by the end of the chapter. For example, the Jacquard loom of 1804 was an inspiration to Charles Babbage who built one of the first mechanical computers in 1822. American inventor Herman Hollerith came across Babbage’s difference engine later that century, and build a machine for tabulating the 1890 census. His company would be acquired by a conglomerate that would become IBM. The in depth story in series of inventions is more interesting than anything I can summarize here.

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Thank you so much for reading our 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 by emailing editor@daniellemorrill.com

Much Love, Danielle & Kevin

What a week! Kevin and I are starting to get the hand of co-editing, though I think we might have pushed the editorial tasks to the end of the week a bit too aggressively. We have more technology helping us with the reading process now, thanks to Kevin’s coding and an awesome startup called Retool (also one of our angel investments) that made it super easy to build the UI. We are able to go through ~50 posts per day in the course of just 1-2 hours and quickly score them as on topic and graded the quality of the content. We’re following ~430 feeds right now, and looking to identify more.

At week’s end we take the top scoring content and whittle it down further based on our editorial perspective on what’s most relevant to readers. Someone has suggested we could turn this into a newsletter-as-a-service business but we are a little early for that… this is still a mostly manual process. However, we are toying around with the idea of starting a second newsletter focused on software development tools, hiring, and practices. Is there another topic you’d love to see us focus on? Hit up the comments!

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 editor@daniellemorril.com

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Danielle & Kevin’s Newsletter With No Name #2

This newsletter is curated by hand with love from Denver, Colorado by Kevin Morrill and Danielle Morrill. You can reply to editor@daniellemorrill.com with any feedback. If you love what you read today, please consider forwarding it so others can subscribe. Thank you

Woo hoo! It’s week #2 of our newsletter that still needs a name (read the 1st issue here). Thank you to everyone who has forwarded this newsletter on to friends and colleagues. If you have open jobs at your startup, just wrote a blog post you’d like us to consider, or have a cool “Request for Startup” idea for the new section we are going to start running please drop us a note with a short blurb no more than 30 words and a link. We can’t promise to include everything, but we’d love to hear from you! 

The Best Thing We Found This Week

Peter Thiel is one of the most interesting vocal personalities in the technology ecosystem, and this interview brings together thoughts on his investing strategy, experiences serving on the board at Facebook for the entirity of its existence (14 years), and our personal favorite: a lot more detail around the founding story of Paypal. “Peter Thiel on Trump, Gawker, and Leaving Silicon Valley”

The headline of the interview is salacious with mentions of our current Cheeto in Chief, a blockbuster celebrity lawsuit, and his move to Los Angeles — but we think the other tidbits we mentioned are the real meat of the conversation.   

From the Operators

Carl Tashian of Nerd Coach digs into startup postmortems, finding founder communication and underlying passion deserve more attention in “What Really Kills Most Startups”

Rand Fishkin of SparkToro reminds us that great marketing doesn’t start with optimizing ad campaigns, but rather understanding what the people you want to reach pay attention to in “You’ve Got Product/Market Fit… What About Marketing/Market Fit?”

Mathilde Collin of Front emphasizes the value of building relationships before you raise in in “Fireside Chat with Founder and CEO of Front, Mathilde Collin”

Patricia Aas of TurtleSec lists “Survival Tips For Women In Tech” (isn’t it sobering that such a list is even necessary?) and Knut Melvaer of Sanity follows on with 23 tips we can all do to help make tech better for women in “Making tech survivable: What Can Men Do”

Russell Smith of Rainforest doesn’t think your startups tech stack needs to be a special snowlake in “5 Foolish Reasons You’re Not Using Heroku”

From the Investors

Congratulations to Austin Clements on his promotion to Principal at TenOneTen Ventures

Kyle Poyar of OpenView lays bare the metrics you need to hit to raise a Series A all the way up to Series D in “What Does It Take To Raise Your Next Round In 2018?”  The full report is also available.

David Beisel of NextView Ventures shows early stage companies how they’re being compared to their peers in “Seed Stage Startups Are Now Graded on a Curve” Founder mental health is on the radar this week

Mahendra Ramsinghani of Secure Octane is now cowriting a book with Brad Feld on Depression, and shares his early observations in “Investors are waking up to the emotional struggle of startup founders”

Felicis has decided to carve out 1% of all checks for exec coaching and therapy

Michael Seibel of Y Combinator details “How to Email Early Stage Investors” and maybe the era of signaling prestige by getting a warm intro is finally over, at least at the angel stage

Diego Rey of Y Combinator claims that “over the last two years, YC has made more seed investments in bio companies than any other investor in the world.” More over, “the percentage of bio companies in each batch has been increasing linearly since 2011.” in “There Are Now 141 Bio Companies Funded by YC”    Are these bio companies getting financing downstream? LifeSci VC breaks down the stats in “Biotech Venture Deal Terms Are More Startup Friendly Than Ever”

Ali Hamed of CoVenture challenges the investing advice of Warrent Buffett and LPs should take notice in “Investing on an 0–2 Count”

Working at a Startup? It’s Time to Learn About Equity Compensation

Our dear friend and Mattermark cofounder Andy Sparks is working on a new startup, Holloway, building tech to help people find, consume, and improve tactical knowledge. Their first guide came out a few weeks ago, offering a comprehensive overview of stock option compensation.   To learn more, check out “The Holloway Guide to Equity Compensation”

This Week’s Book Pick

“The Information: A History, A Theory, A Flood”by James Gleick

Do you know the surprising story of how the Information Age got underway? The Information tells the story from early African tribes and their own form of Morse code, to how England’s need to dominate the seas led tinkerer Charles Babbage on a journey to build the forerunner to ENIAC as early as the 1800s, to information theory pioneer Claude Shannon. After 20 years in software industry, Kevin was surprised to finish the book wondering, “How did I come this far knowing so little about what got our industry going?!”

In last week’s newsletter we featured Scale: The Universal Laws of Life, Growth, and Death in Organisms, Cities, and Companies by Geoffrey West as our book recommendation of the week.

TL;DR 

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.

While building Mattermark I spent the past 5 years studying how companies grow, and exploring how we might detect this growth and describe it using data exhaust that is publicly available online. This cross-disciplinary study, embarked on by theoretical physist West, connected some new dots for when it comes to what growing companies have in common with other scaled up entities. From our thousands of sales conversations, we knew ancedotally that of all the signals we were tracking at Mattermark the most significant (and hardest to get) was employee count. Seeing how the size of a company changes over time is a leading indicator of it’s ability to metabolize capital into revenue. But what can the 8 person version of a startup tell us about the 80 person, or 800-person, version of the future?

This is one of many questions explored in “Scale”

I also loved West’s observation that there is far less written on the death process than on the origins of life and growth (read Ernest Becker’s “The Denial of Death” for one theory on why this is), which reminds me how much less we know about how companies die (or exit). Crunchbase works harder than most data-driven private company platforms to update their “Deadpool” of companies and it’s still incredibly difficult. The knowledge of how to sell companies is also tribal and hard to find, though I am currently reading “The Magic Box Paradigm” by Ezra Roizen and hoping it will become a go-to recommendation for me when founders ask about this in the future. I’ll report back in a future review!

Reading Notes: This book was fantastic as an audiobook on Audible, read at 1.5X speed at is about ~13 hours of listening.

Further Reading: “On Growth and Form” by D’Arcy Wentworth Thompson — West gushes about this book as beautifully written, and it only comes in paper/hardback. It just arrived, and it is loooong. Perfect for the cold Denver winter just around the corner.

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 editor@daniellemorril.com

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!

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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.  — Danielle

I’m excited to write this newsletter alongside Danielle. In order to find, organize, understand the best writing on startups across the web I am using machine learning 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.  — Kevin

From the Operators

Adora Cheung of Y Combinatorinterviews Ooshma Garg of Gobble about the evolution of her prepared meal kit delivery company and 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 “Saved by Zero — Surviving Cancer, Discovering Fasting, and Turning It Into My Next Career Journey   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 “Is the Lean Startup Dead?”   Harj Taggar of Triplebyte provides a hands on guide with actionable advice for “Convincing Engineers to Join Your Team”   Kevin is a moderator for 30 companies in Y Combinator’s Startup School, and this week’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 the story of Weebly’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 can’t wait to see what she invests in next! Arlan Hamilton of Backstage Capital launched the firm’s startup accelerator program this week, and offered commentary on claims that comments to the press were “calling out other accelerators” for their lack of diversity, in a tweetstorm on Thursday evening. Peter Brack introduces his new venture firm Hypothesis 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 Suennen 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 “What’s Next?! A Plan in Progress”   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 ”The NextView Ventures Manifesto”

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 they’re hiring several Software Engineers to solve complex challenges.   Treasury Prime is transforming banking. The company is based in San Francisco, and they are hiring engineers to build modern banking infrastructure for 21st Century.   Enzyme is building FDA compliance and quality systems as a service. The company is based in San Francisco, and they are hiring a Director of Engineering.   * we are angel investors in this company

This Week’s Book Pick

“Scale: The Universal Laws of Life, Growth, and Death in Organisms, Cities, and Companies” 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.

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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 editor@daniellemorrill.com   Much Love, Danielle & Kevin

A friend recommended I read “Ten Arguments for Deleting Your Social Media Accounts Right Now” and while I was initially turned off by the title (see what they did there!) I read it. I don’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 “engagement” (manipulation?) of a large Twitter following. Was I a narcissist? I still don’t know, but what I do know is I dislike who I am when I’m on Twitter and to a lesser extent on Facebook.

It also explores a lot of feelings I’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 I’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. It’s been 24 hours, and I don’t think anyone has really noticed. I’ve been liking some friend’s posts from the web interface when I log in to see what the reaction is to my empty account (nothing). I’m pretty sure hitting publish on this blog post is going to auto-tweet, and I can’t figure out where the heck I set that up so I’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. It’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 didn’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.

I’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 don’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 Kevin’s immediate family to let them know I was taking a break from social media, so not to worry if they didn’t see posts from me and to reach out for 1-on-1 communication by phone, text, or email.

Of all the arguments in “10 Arguments”, the most compelling is the last one — about religion, specifically AI heaven or the singularity. In our race to fulfill this fantasy, we’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 can’t unsee what the author has made clear.

“AI 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 terms—and that is so because AI has no objective criteria for success.”

As someone evaluating companies for angel investment who claim to be building “AI” 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 — this rings so true. I am wearing an old Mattermark shirt that says, “building the basilisk since 2013” and the irony is not lost on me.

In dreams begin responsibilities.

I just discovered this week that I didn’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 let’s backtrack a bit, what is this prototype anyway? It’s a series of Google Docs and Google Sheets chronicling my backlog of personal life crap, recurring stuff like the dentist and habits I’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 I’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. It’s actually too personal for me to share (!!) unlike Facebook. It’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 haven’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 I’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 wasn’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 we’ve all heard this complaint about CRMs before. The sales manager asked the reps why they’re not updating the records, taking notes, logging calls, and really only putting in closed won deals and the answer is usually “I don’t have time” or “there are too many fields to fill in that don’t mean anything to me” or some other flavor.

My mind jumps from here to integrations. If this wasn’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 I’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 API 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. It’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 won’t lie, it’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. I’m really sorry, I don’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.

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. You’d be surprised by how many do! Denver people are the nicest.

I’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 McDonald’s-style “university” 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

In this podcast interview on “Founders Talk” with Adam Stacoviak we talk about the decision to sell my startup 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

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If you’ve been following along on social media, you might have heard me say “I’m on sabbatical” lately. It’s true, I’m no longer an employee anywhere and this break is self-funded (some folks pointed out saying sabbatical sounds like something that I’d negotiated as part of the acquisition), so I’m not sure what to call it. Yesterday was the start of my 9th week of this new phase, and I’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. I’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 I’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 “landed the plane” and I’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 Mattermark’s acquisition in December certainly wasn’t the kind of ending I’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 I’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 tone in an email to common shareholders (I said “I have great news!” before telling common holders they’d been wiped out — not my best choice ever, but also not deserving of so much of the Internet’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, “You have to respond and defend your reputation! Your fans deserve to know the truth! Perhaps a mea culpa?”

After my head stopped spinning I puked in the sink, rinsed it down, and texted my board for advice. “Time to get off the Internet” they said. I focused my last dregs of energy on completing the deal (it closed the next day) and did just that. I’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 company’s strategy. I’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 we’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 I’m a free agent.

I’d love to engage with readers who  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? It’s all on the table.

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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.