Likely running in nature, building software, or gushing about San Francisco. Host of Seven Hills Supper Club 🎙, head of product
@BeInstrumentl
, former founder.
Across my years at Dropbox and Fleetsmith, I’ve screened >1000 resumes, conducted >100 phone screens, and lead >50 onsites for PMs. Both companies have best-in-class product talent 😉
Here’s what top candidates do 👇
When I was 7, my parents set a limit on library books (40/wk) in an attempt to get me to do other stuff. This backfired because I just read all their books in the house including parenting books
After this, I starting giving direct feedback on their parenting & communication 😂
TLDR: I recently made the tough decision to wind down Dayslice and return cash to investors.
A few thoughts on what went wrong and how it feels to return to civilization:
Yesterday, I had an *insane* flying experience
It involved 2 failed landing attempts, a plane full of folks thinking they were going to die, a reroute, and a protest to prevent taking off.
Several passengers called it a "hostage situation"
Strap in, y'all 💺
Their resumes highlight impact of projects rather than just actions
❌Shipped new checkout flow
✅Increased revenue by $5.6m by shipping a new checkout flow that decreased drop off by 6%
IRL, they are thoughtful about attribution & ROI—even though this is often messy & complex
@heyalexfriedman
Sending you love and strength. Currently going through the exact same diagnosis with my dad and it’s hard to articulate how dramatically life, time, and everything else changes with a terminal diagnosis of someone you love.
That's it, that's the story
There's no moral, but I got a frightening glimpse into how preventable disasters can play out: no clear ownership, no critical thinking, blind adherence to process, lack of communication, and fear of financial consequences
/FIN
During whiteboard exercises, they….
🗺Explain how they will approach the problem before diving in
🧠Never pretend like they understand a concept when they don’t — instead they ask questions!
💬Surface the assumptions they’re making
They leverage their “past life” as a PM superpower rather than downplay it
Sales, support, success➡️deep customer empathy, monetization, enterprise intuition
Marketing➡️strategic positioning, telling a narrative
Analytics➡️data driven, experimentation rigor, ML product opptys
They don’t say things like “my” engineers because their worldview isn’t downwards management of resources. Instead, they understand that shipping products is a team sport where the most victorious teams collaborate closely and laterally.
Married
@prescottwatson
yesterday and had a blast gallivanting around San Francisco with the people we love
Highlight was taking
@SFMTA_Muni
with the crew
And on that note, Fleetsmith is looking for our 4th PM! Every product role at Fleetsmith is strategic and there are abundant opportunities for impact, ownership and leadership. Also, you get to work with delightful humans and several office pups 🥰🐶
I’m thrilled to announce that
@DaysliceHQ
has raised $6M from
@upfrontvc
led by
@karanortman
to power solopreneur services businesses!
Quick thread on our mission, our product, and our journey so far 👇🏽
I return in my seat feeling dread, anxiety, and anger.
It feels like we're going to attempt an unsafe landing attempt because of an unwillingness to break chain of command, blind adherence to process, and an airline not wanting to pay a fine.
Instead, she tells me she's also scared, but that we need to trust the pilot and the air traffic control's assessment of whether it is safe
It is literally the least comforting conversation I could have possibly had at that point, but I appreciate her vulnerability
I’ve only missed one flight. SFO ➞ MUC, 10 years ago
I felt so bad because I had to wait another day to get to Munich. But the next night, I got a random upgrade to first class
I reflect on this all the time. So many “missed flights” in life are just upgrades in disguise
As we approach this one, it's just as shaky as the first two, but we make it. We land, and folks around me are crying. This time, tears of joy
I don't even care that we need to sit on the SFO tarmac for another 30 minutes to get off the plane. I'm just grateful to be alive
The job of the CEO is to balance relentless optimism but also confront reality and listen to data.
And once I really looked closely what had and had not worked over the last year, I no longer saw the path to Dayslice being a venture-scale outcome for our investors.
Figma is wild 🤯
We put 300+ people in the same file, at the same time.
Each cursor you see is a Nights & Weekends builder working on nailing the headline + one-liner for the project they're shipping.
Now that I’ve been using it for 6 months, I can definitively say that
@WeCroakApp
, an app that randomly reminds you you’re going to die 5x a day, has radically shifted my perspective on how I allocate time and energy throughout the day
Curiosity is so widely championed but recently I’ve been observing how rare it is. Most people go through life busy collecting signals validating existing beliefs
We’re probably primed to behave this way because most institutions reward immediate correctness over exploration
I do ~3 mentorship calls/month. There's usually no follow-up (which is fine) but I just got an *amazing* email from someone I spoke to in the summer
It was a board meeting-style update for her career.. recent progress, current challenges, specific asks and personalized to me
I've been having a lot of convos on how to tackle early stage exploration w/
@beondeck
It's an exciting stage because of the possibilities but also challenging because you need to create momentum from nothing. Also, when do you re-orient & explore something else?
My tips 👇
Once we get back up in the air, we're told we're being re-routed to Fresno
And let me tell you, I never thought I would be so THRILLED to be en route to Fresno
At that point, I'd take anything over attempting a third landing after what we just experienced
@hailleymari
@joelgascoigne
I used to plan for my work week on Sundays (individual + team priorities, early prep for important meetings, etc), then I moved it to Friday afternoons instead. Highly recommend! Knowing everything is planned for next week *before* I head into the weekend makes it easier to relax
It also makes me think about that saying, “if a tree falls in a forest…” because a lot of the product, business, and cultural details you cared about suddenly vanish into thin air.
Sometimes this feels really eerie.
I’ve often described being a founder feeling like you’re in a forest on your hands and knees, dirt on your face, grasping for user insights and product market fit.
I made a game called Cofounder Quest to find a new collaborator! I'm hiding the game on floppy disks all over the city in places where a software engineer is likely to stumble into it. ⚡️
Enjoy,
Also, I had the rare privilege of having immensely supportive investors—who were there strategically and emotionally through it all.
Thank you especially
@karanortman
@gimmedadeetz
@micahjay1
@starkupnation
for believing in Dayslice & the team.
I debate texting
@prescottwatson
and my parents that I feel like I'm in an unsafe flying situation and that I love them
I'm weighing not unnecessarily alarming them but also not regretting texting them if something did happen
I end up doing it
The flight is AM668 (CDMX —> SFO)
The Bay Area is experiencing intense & unusual weather conditions, specifically, a "bomb cyclone"
I don't know what technically constitutes a bomb cyclone, but it sounds pretty fucking bad. Winds are topping 60 mph, rain is torrential
Spending more time in Bentonville & am enamored by a city that most friends haven't heard of
BTW, the Waltons are pouring billions into making it a cultural epicenter
Below: coffee shop in nature, cheese factory turned concert venue, art museum in nature, wellness & social club
Today was special. I ran my first 20 miler (with more than 1,000 feet of elevation!)
It was also the run that made me feel confident that I can finish the SF marathon four weeks from now 😌
Highly recommend doing SF’s
#CrossTownTrail
— 17 miles & 2400 feet of glorious forests, oceans, sand dunes, dainty neighborhood, ravines, and impeccable views
I ran/walked it this morning and found new spots even as a long term resident
I ❤️ San Francisco
Now, all hell breaks loose
Not a single passenger on the plane wants to get back into the air
People are BEGGING to stay in Fresno and to be let off the plane—even if it means staying onboard for another 7 hours until 10 PM
I also ask what will happen if our 3rd attempt fails. Will we go to a different airport like LAX which has 24/7 customs so we can actually deboard? I'm told we would return to Fresno.
WHY?!
"It's protocol."
Prediction:
@framer
will kill Webflow
Why? Webflow has an ecosystem of experts while Framer makes any designer able to convert designs in Figma to fully functional websites
Our early career designer (0 eng background) maintains & ships redesigns in hours
@Dayhaysoos
@theworstdev
This is exactly why I'm skeptical of technical challenges. We're taking the approach of inviting engineering candidates to work with us on trial basis (1-2 weeks is ideal if they don't have another job) so we can both mutually assess fit. Fully paid ofc!
Hearing the iconic
@arishapiro
(NPR’s All Things Considered) sing alongside
@PinkMartiniBand
was epic tonight
Pink Martini’s casual storytelling (like conversation between friends) between songs makes their shows feel indescribably intimate even when the audience is actually big
@_shankarganesh
@wesleyytian
@Suhail
It's a common thing that basically all founders do (and savvy early employees can do). Google 83(b) election, and you'll find a lot of resources. Here's one to start:
When we try to gain altitude after the almost-landing, the plane falters
In addition to extreme turbulence, the plane drops in the air a couple of times over the course of a few minutes
At this point, everyone on the plane is either screaming or sobbing
Masks are off, infants are crying, a man is throwing up at the back of the plane
It's chaotic, but people are also socially bonding over surviving that landing attempt
I have a habit of sending cold “thank you” emails to writers and chefs whose books and restaurants I really love and based on the near 100% reply rate, I guess it’s rare
When someone has produced an experience or product you really enjoy, it’s worth telling them
Our initial planned departure from Fresno gets delayed because there is chaos in the plane
People just refuse to sit in their seats when we are told we're going to depart
Our new
@DaysliceHQ
website is live today! Check it out at
A quick thread about being scrappy, no-code, and when to invest more/less in different areas of your startup 👇🏽
As we descend (landing attempt
#1
), turbulence increasingly gets really bad. The entire plane feels like it's uncontrollably shaking.
Within 60 seconds of what would have been a landing, the pilots decide it is unsafe and suddenly we are gaining altitude again
After 2.5 incredible, hyper-growth years at Fleetsmith, I’ve decided to leave to embark on figuring out my next adventure. Fleetsmith is a rare place with some of the kindest, smartest people I know — so, needless to say, the bar is *really* high 😌
Here’s what's next …
At this point, no one is concerned. We're just relieved that we're doing whatever is most safe for us. We circle around & then attempt landing
#2
This one is WAY worse. The beginning plays out the same (we almost land but decide at the last moment that the shaking is too severe)
Around 3 hours into us being trapped on a plane on the Fresno tarmac, we get an update.
We cannot de-board in Fresno until 10 PM because there are no customs officers in the airport until then.
Instead, we're going to take off and try (yes, "try") to land again in SF.
“When I founded a startup, I feel like I left civilization. My peers have senior roles at big co’s & I’m in a forest, wandering around on my hands & knees, digging, eating berries off the ground”
A (much more tenured) founder said to me this week & I can’t stop thinking about it
But first, to give you a sense of how truly terrifying that second landing attempt was ...
my plan at this point is that I'm just going to spend the night in Fresno.. HAPPILY
I'm thinking I'll fly back to SF on Monday once the weather has calmed down and it feels safe
I also feel completely out of control. It feels there's nothing I can do to get off the plane, but also not much I can do to prevent it from taking off
I love seeing public spaces designed to facilitate exchange of ideas and human connection.
What if we replaced benches in San Francisco with seats like this? How many more conversations with strangers would we have?
I bet at least one pair of founders would meet this way 😉
Dayslice’s vision was that service businesses should be empowered to focus on what they do best rather than ops.
In the early days of validation, we spoke to hundreds of people selling services through booking links and manually managing a constellation of tasks on the side.
Finally, it is announced that we're going to try again and land at SFO around 5 pm—when winds are supposed to be calmer
We take off, somewhere in the middle of the flight plan, do two confusing loops, and then attempt another landing
@engineering_bae
Highly recommend a redwood grove in Golden Gate Park (for an intimate ceremony) and then a restaurant for the reception near embarcadero — we had forest, city, and ocean as a part of our wedding day which was really special
I get up and go talk to a flight attendant to get a pulse on how the flight crew feels. I'm hoping they'll assure me that what we just experienced is normal to people who 24/7.
There's a rich spectrum of work between "full-time job" and "advisor"
Some examples: org design, vetting "head of" roles, strategy sprints, fundraising strategy, coaching VPs, upleveling planning
You don't always need a full time hire
It’s also a journey I wouldn’t trade for anything because it left me with a sense of unfinished business.
There are other companies to build, more product experiences to obsess over… and as I think about that, I feel the same optimism and excitement I felt in the thick of it.
Although we got a lot of positive feedback and had some signal on willingness to pay, this group also had a large % of folks who saw their income more as side hustle rather than enduring over time—which later revealed they didn’t feel the pain consistently.
A skill I’ve been working on recently is intentionally emotionally resetting every evening
As a founder, it’s easy to accidentally hold on to stuff too tightly
My goal: Great day? No resting on laurels the next. Bad day? Process what’s needed and then leave the emotions behind
Two years ago (!!), I joined a handful of people building
@FleetsmithHQ
out of a house
To celebrate my anniversary, here's a little bit of time travel and takeaways around building early stage teams ✨
Either users were “starters” who had no existing solution so adoption was easy but their pain was not as painful as someone with a full-fledged business.
Or users had an expansive customer base, weren’t too happy with existing solutions, but felt it’d be a headache to switch.
Lastly, I’d be remiss to not mention the best parts of the last 3.5 years: the people.
The teammates alongside I built Dayslice constantly inspired me w/ their customer obsession + grit.
The users who used our product, really loved it, and achieving that is no small feat.
How I feel as an early stage founder filling out a form and putting myself down for literally every contact - the finance contact, the hr contact, and the compliance contact
@engineering_bae
Only in the initial intro call. If it's clear to me that I will not want to continue the interview process, I let the other person know immediately (and with kindness) so neither one of us waste our time. I've done this both as an interviewer and as an interviewee.
@meaganloyst
A question that I’ve had fun asking groups recently is “if you were a micro-influencer in a super niche corner of Instagram, what would be your thing?”
It usually gets people talking about unexpected, wacky things they’re passionate about
📣 for my fellow early stage founders looking for impeccable design talent: working with
@upperstudy
and Linda over the last three months exceeded all my expectations 💫
A common fallacy I encounter amongst non-engineers early in their careers is that working on "strategy" is a way to escape the nitty gritty
In actuality, good strategy requires deep competence across altitudes—from 10,000 feet to the ½ inch view
Embrace the turpentine
Today’s my 30th birthday! So grateful to have had 3 decades on this strange, dazzling planet
I set a theme every decade. A few thoughts on my last decade, what’s to come, and the beauty of long-term personal initiatives—
I’m at a poker night with a few founders + others and as a joke, we decided intros should include: name, company, whether you’ve found PMF
Best answer was actually from the Meta employee, deadpan, “we found PMF and now we’re on our way to losing it” 💀
I am *so* excited to make intros + help her get to the next step in her career
It made me reflect on how a lot of folks ask for mentorship but the most skillful way is inadvertently recruiting mentors by being the type of person who is really easy to support and root for
@briannekimmel
@Rachel_Delacour
@anneraimondi
@mikkelsvane
👏🏽 love this. It reminds me of a quote I stumbled upon recently that resonated with me: “Remember that you once dreamed about being where you are now” especially useful reminder for those of us who are super future-focused and always working towards the next goal
Three offers signed in the last 48 hours.. and just like that, our small but mighty team at
@DaysliceHQ
has doubled 😌
The most energizing aspects of being a founder: the team & your customers 🎁
@GergelyOrosz
Companies definitely need to use a threshold of product engagement to decide when to send these.. I feel like it's almost a reminder of how a product *hasn't* delivered that much value to you over a full year of use
The best part about early stage is the ability to quickly integrate cutting edge tech and impact the customer in a meaningful way
A quick walkthrough of how we integrated AI to solve a real customer need in just a few weeks 👇🏽