Internet entrepreneur/advisor: 2 exits & now own a portfolio of 7-figure companies. Sharing deep dives on world class startups, founders & customer experiences
The biggest acquisition no one's talking about is Zillow buying
@followupboss
for $500M in all cash
And they've intentionally stayed under the radar despite being ahead of every trend
Bootstrapped
Profitable
Community
Vertical SaaS
Here's their 12 yr overnight success story ⬇️
Like everyone else, I was moved by Tracy Chapman & Luke Combs at the Grammy's
Tracy's an anti-celebrity:
-uncomfortable in the public eye
-doesn't own a smart phone
-not on social
There isn't a lot of info on her
But here's what I found on her and the history of Fast Car 🧵
8/And at the 2024 Grammy's Tracy and Luke won everyone's hearts and soul, because of
1. The juxtaposition of an unlikely duo
2. A genuine respect & chemistry
3. And most importantly... Fast Car being a universal & unifying song for the human struggle - poverty
Simply beautiful
5/Tracy was scheduled to perform at Nelson Mandela's 70th Birthday Tribute
After Stevie Wonder had technical difficulties & didn't perform, Tracy went on stage to perform Fast Car with just a microphone and her guitar
This propelled the song to the top of the Billboard charts
The last 3 years have been nuts for
@Usher
-Vegas residency: $115M sales
-Super Bowl performer
-New album: Coming Home
-New tour: Past Present Future
But it hasn't been an accident
It's been a strategic masterclass in beta testing, iterating & core product focus
Here's how⬇️
7/Luke covered Fast Car in 2023, because
"My dad had that record & would play it all the time. That was just one of the first songs really that I ever remember hearing listening to... it's always just been one of my favorite songs for my entire life"
It won CMA song of the year
4/Tracy wanted to form a band but instead stuck to being solo, bc "every song was moving, every song meant something — it was all driven by passion"
Fast car was the 1st single off of her debut alum was released on April 6, 1988
And another big break would come 3 months later
2/Tracy played music since the age of 3 and wrote songs since the age of 8
Her high school yearbook said "Tracy Chapman will marry her guitar & live happily ever after”
And that's what happened
Her big break came at Tufts University, where she thought she wanted to be a vet
1/Tracy was born and raised in Cleveland, by a single mom who brought her up to be a free thinker
She loved reading, poetry & music
And she saw education as her "way out of Cleveland, and out of poverty"
At 16, she won a scholarship to a private boarding school in Connecticut
3/Classmate
@briankoppelman
(creator of Billions) saw Tracy performing at Tufts and intro'd her to his dad, who ran SBK, a top indie music-publishing company
He told her: "You know, I never do this, bc I try to be my own person, but I really think my father could help you"
6/Tracy went on to release 7 more albums, but Fast Car was was brought her her most commercial success
She parlayed this to using her platform to support causes she cares about, and has been mostly out of the spotlight ever since her last album in 2008
Until
@lukecombs
...
I think the business of religion is going to explode, because of Gen Z and America's loneliness epidemic.
It already generates more revenue than APPL ($383B), GOOGL ($297B) and MSFT ($211B)…combined
So deep dived and came up w 18 business ideas to capitalize on the trend: 🧵
I’m part of a few founder groups of $1M to $100M+ net worth folks in multiple industries
The common theme of the real killers are
-Speed from idea to execution
-Speed of iteration
-Consistent bias for action over months/years/decades
It’s a daily reminder to just do & level up
Like everyone else, I was moved by Tracy Chapman & Luke Combs at the Grammy's
Tracy's an anti-celebrity:
-uncomfortable in the public eye
-doesn't own a smart phone
-not on social
There isn't a lot of info on her
But here's what I found on her and the history of Fast Car 🧵
5/Usher's 2022 performance on NPR's Tinydesk validated why fans resonated with him
It also created a viral moment that helped add more momentum for his "comeback"
“I went to Tiny Desk and I literally sang my classic records. And people loved it”
Craigslist unbundled in the 2010s
Upwork is unbundling in real time due to
1. Remote work
2. Specialization
3. Quality control
4. Trust/security
And bootstrappers & influencers are starting these companies
Here're 37 disrupters from Accounting to Writing ⬇️
Accounting
1. Paro
@HERMusicx
@Usher
Usher pulled out all the stops and no detail went overlooked
Loved how he reinvented himself and his classics
Did a deep dive of this if anyone’s interested
The last 3 years have been nuts for
@Usher
-Vegas residency: $115M sales
-Super Bowl performer
-New album: Coming Home
-New tour: Past Present Future
But it hasn't been an accident
It's been a strategic masterclass in beta testing, iterating & core product focus
Here's how⬇️
11/My key takeaways from Usher's last 3 years renaissance
1. Identify your competitive advantage
2. Focus on your core audience
3. Start with a small test
4. Iterate > keep testing > validate
5. Double down on user needs
6. Surprise and delight your community
7. Keep compounding
@HarrietEve9
What can't this man do… and at 45 years old!
Love how Usher reinvented himself and his greatest hits in the last 3 years to headline the Superbowl
I did a deep dive on it if anyone's interested
The last 3 years have been nuts for
@Usher
-Vegas residency: $115M sales
-Super Bowl performer
-New album: Coming Home
-New tour: Past Present Future
But it hasn't been an accident
It's been a strategic masterclass in beta testing, iterating & core product focus
Here's how⬇️
7/Usher's show focused on his core fans
“I really wanted to give women something to look forward to, something to come here to Las Vegas with their friends for... They’ve been saving up all year and were able to manage to get away from their kids or get away from their problems”
8/This is a good lesson in listening to your core audience & doubling down on your competitive advantage
For Usher it's his live shows, which is hard to capture on social - the experience, feeling & community
But it also can't be copied by a Soundcloud, Youtube or TikTok artist
12/I've been a big Usher fan since 8701 (middle school)
I also saw his Vegas residency, which was one of the best concert experiences I've ever had
My top 5 songs are:
1. Confessions Part II
2. Burn
3. Nice & Slow
4. U Got It Bad
5. U Don't Have to Call
4/The show brought the ATL to Vegas
-A roller rink
-Magic City's strip club
-A jazz club
-A parade
“No one has ever brought Atlanta culture to Vegas. Roller skating is a major part of the culture in Atlanta. The strip club scene is a major part of the culture in Atlanta”
My wife is a professional baker & always raves about this tiny $200M+ baking company in Vermont
But not just about its quality flours
She LOVES its customer experience and community
So I did a deep dive & King Arthur Baking co is a masterclass that every startup should steal:
2/His newer music hadn't resonated
So he went back to the basics & his superpowers
- Classic R&B hits
- Singing, dancing, performing
-Core female fans
And innovated on his show experience
"I can’t be who I was. I don’t want to be who I was. I want to be better than what I was"
3/Usher used his 1st 2021 Vegas residency as a testing ground
He hadn't done a full tour in 6 years, but it was a success
- Caesars Palace: 4,100 seats
- 20 shows (sold out 18)
- 84K tickets sold
- $18.8M ticket sales
More importantly it gave him insights into what fans wanted
The last 3 years have been nuts for
@Usher
-Vegas residency: $115M sales
-Super Bowl performer
-New album: Coming Home
-New tour: Past Present Future
But it hasn't been an accident
It's been a strategic masterclass in beta testing, iterating & core product focus
Here's how⬇️
@miguelitopty
So many hits he couldn’t get to em all
Loved how he reinvented himself and his classics
Did a deep dive of it here for anyone who’s interested
The last 3 years have been nuts for
@Usher
-Vegas residency: $115M sales
-Super Bowl performer
-New album: Coming Home
-New tour: Past Present Future
But it hasn't been an accident
It's been a strategic masterclass in beta testing, iterating & core product focus
Here's how⬇️
1/Usher's a hit machine with nine
#1
singles and eighteen in the top 10
But his last one was OMG in 2010
Despite making albums & staying relevant, he hasn't had the same commercial success since Confessions in 2004
This was pre Youtube, Spotify, Instagram, Soundcloud, TikTok
I co-hosted a dinner with this week with 10 founders who have collectively sold companies for $500M+ and companies have done $600M+ in revenue
Here are 7 common threads of the 1% founders:
1. More than community, folks are looking for real connection. Founders meet lots of
6/A bigger stage was set for his 2nd residency that ended in 2023
- Park MGM: 6,400 seats
- 80 shows
- 394K tickets sold
- $95.9M ticket sales
Between his 2 Las Vegas residencies
- 100 shows
- 478K tickets sold
- $114.7 ticket sales
- $1.15M ticket sales per show
1st time founders focus on product
2nd time founders focus on growth
3rd time founders focus on team
Here’s everything I’ve learned about hiring and team building since my first startup 15 years ago
- Early teams need more generalists
- As you grow, you need more specialists
-
@girdley
Japan would like a word…
Snow Skiing in the EU vs The USA vs Japan
US: "Go hard. Push yourself. Athletic endeavor!"
EU: "Would you like wine with lunch?"
Japan: "Let's enjoy the harmony of nature and sport."
US: Chicken fingers and frozen fries with a Pepsi. $25.
EU: Homemade
9/This Sunday Usher will be headlining the Super Bowl halftime
Making him the current King of Las Vegas
And culminating 3 years of testing, iterating & reinvention
He's not getting paid, but it'll boost:
albums
streams
concerts
brand deals
investments
Apple Music pays the NFL $50 million annually to sponsor the Super Bowl halftime show.
But Usher won't get any of that money.
Instead, he'll perform for free, leveraging the exposure to gain followers, sell tickets, and increase streaming numbers.
Here's how it works 👇
The CEO of a $75M rev company called me yesterday
She said she was resigning after 1 year as CEO
She had...
1. Risen through the ranks over the last 30 years
2. Went through 3 acquisitions
3. Transitioned from COO to CEO after the last acquisition
The reasons for resigning:
-
I co-hosted a dinner this week with
@sulemanali
for 10 other founders in SF who have collectively built tech companies generating $750M+ of revenue
Here are 12 observations of the 1% founders:
1. SF is home to builders. 9 out of 12 founders moved to SF to start companies.
2.
@franklinleonard
Loved this intimate and detailed breakdown of a unifying moment
Here’s another one on how Tracy Chapman was discovered, the history of Fast Car, and why the Luke Combs collab was magic
Like everyone else, I was moved by Tracy Chapman & Luke Combs at the Grammy's
Tracy's an anti-celebrity:
-uncomfortable in the public eye
-doesn't own a smart phone
-not on social
There isn't a lot of info on her
But here's what I found on her and the history of Fast Car 🧵
I think the business of religion is going to explode, because of Gen Z and America's loneliness epidemic.
It already generates more revenue than APPL ($383B), GOOGL ($297B) and MSFT ($211B)…combined
So deep dived and came up w 18 business ideas to capitalize on the trend: 🧵
Here's the longest Twitter post ever about becoming an "overnight success."
I researched:
1. An A to Z list on how many years it took 105 startups to IPO
2. 23 of the most popular Tweets from business leaders, athletes, and artists on the reality of an "overnight success"⬇️
The avg founding CEO tenure is 6 years
Mark Zuckerberg's 20 year CEO Facebook journey has been a masterclass in social PR & EQ evolution
And Zuck's recent IG glow up is his "EQ Eras Tour"
Relatable
Authentic
Mind blowing
Here're 18 IG post examples⬇️
@Ludacris
@Usher
Your favorite artists favorite artist
Love how Usher reinvented himself and his classics
Did a deep dive of it here if anyone’s interested
The last 3 years have been nuts for
@Usher
-Vegas residency: $115M sales
-Super Bowl performer
-New album: Coming Home
-New tour: Past Present Future
But it hasn't been an accident
It's been a strategic masterclass in beta testing, iterating & core product focus
Here's how⬇️
If you want to read more on Usher's Las Vegas revival check out this article from last year
H/T
@hunteryharris
and
@paridukovic
intimate article and amazing visuals
A tech company that isn't talked about enough is
@builtwith
for bootstrapping to $14M+ year and 0 employees
And their evergreen playbook should be copied by indie or VC backed founders for
Organic growth
Compounding
Focus
Building on your own terms
Here's the 17 year story⬇️
The last 3 years have been nuts for
@Usher
-Vegas residency: $115M sales
-Super Bowl performer
-New album: Coming Home
-New tour: Past Present Future
But it hasn't been an accident
It's been a strategic masterclass in beta testing, iterating & core product focus
Here's how⬇️
@JoePompliano
Every client listed was the leading candidate for the Bama job
What a flywheel
1. Recruit more coaches to rep
2. Have those coaches help him recruit NFL players to rep
3. Use the reputation of NFL players to rep high school NIL kids
4. Help funnel high school kids to his coaches
@gregisenberg
Glad this is on your radar. I’ve worked with and known
@DevInTheLab
when he was just getting started.
Here are some other things I think he did really well:
1. Leaned into the Asian market. His first video training a Chinese kid blew up and took him around the globe while hoops
@oneilgerald_
@studiopixie
100%
And the kicker is that he's doing this at 45 years old!
Love how Usher has reinvented himself and his greatest hits from the nostalgia tour to the Super bowl in 3 years
I did a deep dive on it if anyone's interested
The last 3 years have been nuts for
@Usher
-Vegas residency: $115M sales
-Super Bowl performer
-New album: Coming Home
-New tour: Past Present Future
But it hasn't been an accident
It's been a strategic masterclass in beta testing, iterating & core product focus
Here's how⬇️
@kevinleeme
That’s a great one.
Here are a few for me:
1. Drinking glasses vs glass tomato jars
2. Tupperware vs yogurt containers
3. Reusable shoe storage bags v plastic grocery bags
@ForbesBLK
No surprise there.
The man has reinvented himself with startup like strategy over the past 3 years
Did a deep dive of it here if anyone’s interested
The last 3 years have been nuts for
@Usher
-Vegas residency: $115M sales
-Super Bowl performer
-New album: Coming Home
-New tour: Past Present Future
But it hasn't been an accident
It's been a strategic masterclass in beta testing, iterating & core product focus
Here's how⬇️
@JoePompliano
@stoolpresidente
This has probably already hit your desk, but in the off chance you've been too busy trying to find a Stanley Mug this week, thought I'd help you out...
It's right up your alley:
@UMichFootball
x Business x Media⬇️
It's official.
@HubSpot
is sending me & 7 friends to sit 50-yard-line at the College Football National Championship.
The deal is simple.
They're paying for our seats. We're gonna do some awesome, creative sh*t to market the brand & hopefully go viral.
Much much more to come,
@notgwendalupe
The problem of having too many hits
One of the best halftime shows but still missing out
Though loved how he’s reinvented himself and the classics
Did a deep dive here if anyone’s interested
The last 3 years have been nuts for
@Usher
-Vegas residency: $115M sales
-Super Bowl performer
-New album: Coming Home
-New tour: Past Present Future
But it hasn't been an accident
It's been a strategic masterclass in beta testing, iterating & core product focus
Here's how⬇️
Your Dad with a Handycam
Your Mom by your side
But it's not your 1st day of school
You're 32 y/o
It's your new company's 1st day at the new office
Your family's moving you in
You're about to start the largest SaaS company of all time: Salesforce
What a moment. What a dream⬇️
@Usher
Loved how you’ve reinvented yourself over the last 3 years and moved like a startup to get to this moment
Did a deep dive of it here if anyone’s interested
The last 3 years have been nuts for
@Usher
-Vegas residency: $115M sales
-Super Bowl performer
-New album: Coming Home
-New tour: Past Present Future
But it hasn't been an accident
It's been a strategic masterclass in beta testing, iterating & core product focus
Here's how⬇️
@RealBrittain
One of the best halftime shows and he didn’t even get to all of his hits
Loved how he’s reinvented himself and his classics
Did a deep dive here if anyone’s interested
The last 3 years have been nuts for
@Usher
-Vegas residency: $115M sales
-Super Bowl performer
-New album: Coming Home
-New tour: Past Present Future
But it hasn't been an accident
It's been a strategic masterclass in beta testing, iterating & core product focus
Here's how⬇️
Stanford startup founders raised the most money ($73B) from 2013-2023
But they don't have the most IPOs in the last 3 years
I'm starting an in-depth analysis on recent IPO'd tech founders
Here's what the early data shows from:
63 IPOs
160 founders
87 colleges they attended🧵
I started tweeting daily in 2024
I’ve also developed phone/internet addition & hate the downsides
I’ve talked to social influencers & am part of a founder “phone accountability” group - everyone’s hyper aware of it
Here’re my experiences:
1. Screen time has doubled
2. I
I've observed that a common trait of 10x founders and builders is a strong bias for action
-Talking to the customer
-Shipping the product
-Updating the documentation
-Writing the post
-Sending the email
-Making the call
-Not avoiding the hard things
Here're 20 post examples
@india_regal
What didn't he do?!
Love how Usher reinvented himself and his greatest hits
He was close to staying on the nostalgia tour and then made it to the Super bowl in 3 years!
I did a deep dive on it if anyone's interested
The last 3 years have been nuts for
@Usher
-Vegas residency: $115M sales
-Super Bowl performer
-New album: Coming Home
-New tour: Past Present Future
But it hasn't been an accident
It's been a strategic masterclass in beta testing, iterating & core product focus
Here's how⬇️
@FoundersPodcast
Really good example of the power of patience
I’ve found that a big reason I struggle with this is because I’m trying to compress time and see more results/growth now
But the reality is that you can’t beat time for most enduring things
6/As the number of "religious" organizations grow, so will the number of specific business needs and the spending to support these organizations.
Here are 18 business ideas worth $1M-$1B to capitalize on the Religion 2.0 trend and challenge the incumbent tools and services:
I co-hosted a Hampton dinner in SF with
@shivanisberry
for 12 founders who have IPO’d companies, run $100M+ rev businesses, and built 3M+ social followings.
The crazy part is that none of these “accomplishments” were ever brought up.
Here are 8 topics that did:
1. Community.
@gregisenberg
Here are a few that I'm thinking about:
1. The rise of curation
2. Influencer's being the new Demand Gen role for SaaS/B2B businesses
3. Pooling resources for communal living with friends/family
4. Continuing education for knowledge based professionals
One of my favorite Twitter follows that's blowing up is
@pronounced_kyle
He's the
@BillNye
for deep tech Twitter by making it
- Accessible
- Entertaining
- Approachable
He's also a masterclass in creating for Twitter
Here's how he's done it through his X most liked posts ⬇️
@mikekarnj
Have seen a similar trend.
Other potential reasons…
- cost to start a company has gone down
- … esp w more remote work and no need money for an office to start
- if founder has an audience, their CAC has gone down and the speed to get first 100 customers is faster
@JoePompliano
@TickPick
Wow
Usher’s made all the right moves over the last 3 years to reinvent himself and operate like a nimble startup
Did a deep dive of it here if anyone’s interested
The last 3 years have been nuts for
@Usher
-Vegas residency: $115M sales
-Super Bowl performer
-New album: Coming Home
-New tour: Past Present Future
But it hasn't been an accident
It's been a strategic masterclass in beta testing, iterating & core product focus
Here's how⬇️
Here's how I think SMB & prosumer startups will be built in the future:
Distribution
- Build audience. Then product
- Build social (proactive). Then SEO (reactive)
- Poach existing communities
- Build own community (digital/physical)
- Content 1st (organic growth)
- Content
@drgurner
It's pretty common in Asian families
We intentionally bought a multi-unit "family compound" so my mom could live on one of the units
I've found it to be a major benefit to
- not have to worry about her due to proximity
- have childcare support
- have multigenerational living
I've noticed a trend where SaaS/B2B founders
1. Avoid outbound sales at all costs
2. Then need to accelerate growth
3. So they start outbounding
4. They struggle
5. Then declare outbound doesn't work
But the bigger issue is they miss the first principle of B2B sales: Trust
@markjenney
Spend a night or 2 at a traditional Ryokan w an onsen. You’ll appreciate the experience/hospitality and relaxation as a Airbnb guy.
What cities are you going to?
@KingJosiah54
Dude is the triple threat: singing, dancing and performing
And he's doing it at 45!
Also loved how Usher reinvented himself and his greatest hits
I did a deep dive on it if anyone's interested
The last 3 years have been nuts for
@Usher
-Vegas residency: $115M sales
-Super Bowl performer
-New album: Coming Home
-New tour: Past Present Future
But it hasn't been an accident
It's been a strategic masterclass in beta testing, iterating & core product focus
Here's how⬇️
@FoundersPodcast
1. Identifying A+ talent and recruiting them to your company is tough.
In any field talent spotting is the difference between good and elite.
Think about how many top draft pick in sports never pan out.
2. You really are the average of the people you surround yourself with.
@danielwjones_
lol what can't this man do
Love how Usher reinvented himself and his greatest hits in the last 3 years to headline the Superbowl
I did a deep dive on it if anyone's interested
The last 3 years have been nuts for
@Usher
-Vegas residency: $115M sales
-Super Bowl performer
-New album: Coming Home
-New tour: Past Present Future
But it hasn't been an accident
It's been a strategic masterclass in beta testing, iterating & core product focus
Here's how⬇️
Over the past year, I've advised SaaS startups and talked 50+ founders in the $1M-$15M ARR range
This is the "messy middle" (h/t
@scottbelsky
)
It's where startup's plateau or build the foundation for true scale
Here's why?
- You can brute force your way to $1M ARR
But you
No one is self-made.
There are:
- parents who believed in you
- significant others who paid the bills
- 1st customers who took a chance
- advisors who guided you
- 1st investors who wired money
- college alums who made intros
- teachers who inspired you
- coworkers who supported
The last 3 years have been nuts for
@Usher
-Vegas residency: $115M sales
-Super Bowl performer
-New album: Coming Home
-New tour: Past Present Future
But it hasn't been an accident
It's been a strategic masterclass in beta testing, iterating & core product focus
Here's how⬇️
I started tweeting everyday since January 1, 2024
And just reviewed the first 10 days of metrics
Here's what I've learned after my first:
- 10 threads
- 532 tweets (2 viral)
- 704 followers
- 4.2M impressions
*The is not twitter advice. Please consult with a twitter expert*⬇️
If you're interested in more culture and business breakdowns, here's one I did on how I think religion is going to explode, because of Gen Z and America's loneliness epidemic.
I think the business of religion is going to explode, because of Gen Z and America's loneliness epidemic.
It already generates more revenue than APPL ($383B), GOOGL ($297B) and MSFT ($211B)…combined
So deep dived and came up w 18 business ideas to capitalize on the trend: 🧵
One of my companies is a call center for pizza restaurants. Today is the busiest day of the year
And everyone puts in orders 30 mins before kickoff
Pro tip to help your local pizza joint & yourself: Get your pizza earlier in the day & reheat it in the oven
Here’s why:
1. Pizza
YC is a startup hits machine: 18 IPOs, 38 exits & hundreds of unicorns
And YC's secret sauce: Do things that don't scale
Stripe (YC S09 / $53B valuation) embodied this ethos in every part of their CX in the early days
sales
onboarding
support
user feedback
Here's how⬇️
A trend I've noticed is software companies using human support and implementation as a competitive advantage (especially SMB ones)
I think this is a positive shift away from treating support as a cost center, deflecting customers and 100% AI
Here's why:
1. Reducing friction to
Last week, I had drinks with 2 senior managers of $25M+ ARR startups that I used to advise
They all said that company moral and team output is higher than ever
In 2022, many of these folks were still
- Job hopping for higher roles and salaries
- Negotiating raises <1 year in
@jowyang
$1.625M is a really good investment when you consider the potential ROI of garages in the area.
The range in ROI is 18,461x to 1,846,153x from just 3 examples below.
It's just math.
Apple: $3T Market Cap
Google: $1.76T Market Cap
HP: $30B Market Cap
And today’s deep dive is on a baking company that created something called “The Baker’s Hotline” to create a world class customer experience for bakers
My wife is a professional baker & always raves about this tiny $200M+ baking company in Vermont
But not just about its quality flours
She LOVES its customer experience and community
So I did a deep dive & King Arthur Baking co is a masterclass that every startup should steal:
Fact: The 10 year "overnight" success
Fiction: The overnight success
Here’s how long it took these 105 tech startups to IPO:
Affirm took 9 years to IPO
Airbnb took 12 years to IPO
Alarm took 14 years to IPO
Angie’s List took 16 years to IPO
Appfolio took 8 years to IPO
@schwartzsteins
Very consistent and on-brand with with the formation of the Tunnel Worker's Union and "The Blue Collar Man" since the
@StanfordFball
days.
More on the Tunnel Worker's Union:
"Allow me to reintroduce myself..." for all new and old followers👇
👋My name's AJ. Generalist founder, 2x exits and now own a portfolio of 7-figure internet/agency companies.
Career 🚀
I've built my career growing VC backed and bootstrapped tech start-ups in SaaS, mobile dev