Jess Chan
@jjesschan
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Diary Of An Entrepreneur | Built @longplaybrands & now @heybackbone . $300M+ generated for DTC. Tweets on building a Retention Ecosystem & the journey to SaaS
Toronto
Joined January 2023
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Pinned Tweet
Been thinking about starting a "Diary of An Entrepreneur" series for a while & figured the best way is to just pull the trigger.
In the spirit of Building In Public, I want to start a conversation around the actual day-to-day emotional & psychological journey of being an
15
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155
My screen time is getting out of control. I can literally feel my brain chasing dopamine hits multiple times a day.
Any tips for breaking this habit?
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2K
We wanted to break the internet. And we did.
@AaronOrendorff
,
@AndrewDurot
& I put together THE most comprehensive collection of everything you need to nail down EVERY. STEP. OF. YOUR. FUNNEL (and beyond).
1) Beyond The Funnel LTV Playbook by
@longplaybrands
- 91 pages
-
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988
Hey, I'm Jess👋
I've spent 8+ years helping DTC brands with retention marketing. Then I built
@longplaybrands
&
@heybackbone
.
We've generated $300M+ for 7, 8 and 9-figure brands like Dr. Squatch, oVertone, Dr. Harvey's, iRestore & Boxed Water.
We've helped brands accomplish
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How can I improve customer retention and increase LTV?
That's the
#1
question we get from generating $300M+ in revenue through retention marketing for DTC brands.
And what I can tell you is...
Email & SMS marketing isn't enough.
Our
@longplaybrands
team has refined our
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VIP behind-the-scenes look at how I ended up here ft. a classic
@thesamparr
savage backhanded compliment about my face 🤣
.
@jjesschan
- Owns an ecom and saas biz
- Double blackbelt in taekwondo (god dam)
- Toronto based
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Drinking water is the daily habit I've been trying to start for 10+ years and have failed miserably.
What're some tips to drink water regularly?
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5
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One of the biggest mistakes ecom brands make?
Small brands trying to emulate big brands without realizing that a lot of their tactics only work now BECAUSE they're big.
What are the most common tactics you've seen brands trying to copy that don't work until they're big enough?
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Anyone have a recommendation for a freelance designer that can do basic designs to illustrate concepts (eg. marketing funnels, graphs, venn diagrams etc.)
Don't need crazy creative designs, I'm talking napkin-sketch style with simple lines/shapes.
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wow ironically I was away from my phone for like 5 hours & this blew up 🤣
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2016: DTC Ecom is magical
2017: DTC Ecom is the best business
2018: Everything we touch turns to gold in Ecom
2019: Ok we have to try a little harder
2020: We're good but scared
2021: I'm a genius & we're 1000% up YOY
2022: nvm, turns out everyone was making money
2023: ecom is
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Diary Of An Entrepreneur Series continued...
Day 72:
- got a spine tattoo today ✌️I've wanted a piece from this artist for ages & he's usually impossible to book. And he literally did the entire design from scratch AND tattooed it in < 3 hours. Mastery is so f*cking incredible
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went back & forth on whether it was a good idea to share this cus Twitter/X isn't exactly the best for nuanced conversation lol but f*ck it 🤷🏻♀️
I have so many mixed feelings on this. So here goes...
On the other hand, I have fully felt this sentiment as a female entrepreneur,
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After 4+ years of running an agency, tracking our MRR is probably the lowest on my list of "important metrics to know" when it comes to actually making strategic decisions.
These are the 8 metrics you should be monitoring that have been most important for me 📈
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I’m so tired of hearing about how everyone scaled to a bajillion $ in a second.
Tell me about the weirdest quirk about you.
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9-figure brands aren't built on just the single silver bullet of "a great ad creative".
There's a whole engine behind-the-scenes to make the acquisition costs, first-order & LTV economics make sense.
We ran retention marketing
@longplaybrands
for Dr. Squatch for years & while
Dr. Squatch really built a 9-figure business business selling $7 bars of soap. That still blows my mind. The game must have been so different 2-3 years ago.
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I absolutely hate these "entrepreneur misery stories" that perpetuate how the idea that if you're not suffering, you're not working hard enough.
Sure, there are hard times.
But I don't want to suffer for my business. I wanna thrive alongside my business.
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Every entrepreneur goes through a period of intense loneliness.
When you've outgrown your childhood friends & you don't have anyone around who understands the challenges you're dealing with every day.
It's a rite of passage.
Mine was rough, but then you find your community 👇
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WOOOOT, so excited & honored to have shared this absolute "no holding back" deep dive with the
@HamptonFounders
community!
I haven't been nervous for a talk for a while, but definitely got some butterflies for this one just because of the sheer calibre of this community 🔥
Our member,
@jjesschan
has driven $300m for DTC clients via retention marketing in the last few years.
This week, she opened her team's playbook, including:
-Their audit process
-Crucial email/SMS flows
-Benchmark performance data
-and more...
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Diary Of An Entrepreneur Series continued...
Day 56:
- Wow so wild day LOL. Didn't know
@thesamparr
's tweet was going live today but it's all fun and games 🥳 I literally don't even do dating apps so I was unprepared for the social anxiety spiral I went down 😂
- TBH I don't
Been thinking about starting a "Diary of An Entrepreneur" series for a while & figured the best way is to just pull the trigger.
In the spirit of Building In Public, I want to start a conversation around the actual day-to-day emotional & psychological journey of being an
15
3
155
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Email & SMS aren't dead.
But they ARE the bare minimum.
And in this day, the bare minimum can't scale a DTC brand to 7, 8 or 9-figures.
You need the Retention Ecosystem for:
- Multiple Channels
- Repeat Purchases
- Customer Insight
- Word Of Mouth
Here's a breakdown (🧵):
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Incredibly excited to announce the launch of our
@longplaybrands
X
@socialsnowball
collab on Mastering The Customer Lifecycle
We've put together the most in-depth course on retention marketing including:
1. Retention Marketing 101
2. Understanding The 4 Pillars Of Retention
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I wrote an article for
@HamptonFounders
recently on the journey from agency to SaaS.
TL;DR - It's hard & I was wrong about most things
Good News: That's entrepreneurship 🤷♀️
5 hard lessons so you can avoid them👇
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@ShaneAParrish
1. Don't care about the opinions of people you wouldn't take advice from.
2. Everything is working FOR you - but only if you can figure out how.
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Remember when you wanted everything you have now.
Because one day, you’ll have everything you want now.
And you’ll feel the same.
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This was my first year on Twitter/X and I decided to commit to posting regularly to give it a shot
And then started my
#diaryofanentrepreneur
series
I was hesitant for a while because I'm soft & I cry easily 🤣 and didn't know if sharing publically & openly would be too
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I used to love the adrenaline rush of hearing how someone scaled to $10M in 12 months.
Now I'm way more interested in people who've been able to run their business for 12+ years.
I'm going all in on playing the long game 🥳
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Y'all, life is so f*cking great. I'm happier than ever & its all in the little things like only having calls 2x per week, going on impromptu walks with badass entrepreneur friends, hosting dinner parties & being able to buy everyday things that were "luxury" years ago 💗
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How many times did you think "we're so royally f*cked & this is the end" in the first year of starting your business?
It was at least 3 times a week for me.
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Anytime I meet an entrepreneur who's still super protective of their ideas, my main thought is...
"You're super new to this game, aren't you?" 😂
Ideas are easy. Execution is the hard part.
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Every founder walks this path at some point.
I walked mine last year. And it led to the greatest 6 months of business growth we've ever had (and still going!).
Here's a blog post I wrote for
@hamptonfounders
on all the mistakes I made 👇
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Buying cut mangoes at Whole Foods is still the ultimate form of luxury to me.
What're your little "I made it" moments?
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I've wanted to start a "Things I Was Wrong About" blog series for a while and SO excited to launch the first one with
@HamptonFounders
🔥
It's the next phase of sharing the real journey of entrepreneurship as part of my Diary Of An Entrepreneur Series!
Here I'm sharing all the
Founders, here's an exercise you can use to diagnose problems in your company
It comes from Jess Chan, who has a background in theoretical calculus and bootstrapped her agency to 7-figures in it's first year.
Something not working in the biz? Ask yourself these 5 questions 👇
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Entrepreneur Life Update:
Getting to casually decide to live in Lisbon for 2 months
... having my parents fly in for a week
....then stepping out for 2 weeks to travel with my love when he arrives
... all while coming off the best growth period for
@longplaybrands
and
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I find it 10x more irritating to book a call through someone's assistant, than through a calendar link.
Is it just me?
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wowowow I'm maximum-level excited to share this podcast with
@iamjennkamara
🥹 this was one of my favorite podcasts to record ever.
It was so beautiful & rare to get to share the honest human side of the entrepreneurial journey and SO in alignment with the conversations I
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Every agency owner discovers this...
Your lowest paying clients are always the most difficult.
Why?
Here's what I think:
Small budget clients are often limited in their mindset which has kept their business small and is why they don't have the budget.
Large budget clients
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i finally have a coffee shop where they ask me if I want "the usual" & if I got my tattoo yet
& a cute old construction worker named Steve that says good morning to me every day
and it's these little bits of human-ness that make my day & make life great ✨
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Remember when you wanted everything you have now.
Because one day you'll have everything you want now.
And you'll feel exactly the same.
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Is it just me or does buying a physical copy of Hormozi's $100M Leads feel wrong?
Some books just have "ebook energy" you know?
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Diary Of An Entrepreneur Series continued...
Day 25:
- it was my turn to be in the hot seat on our monthly
@HamptonFounders
cohort call today and it was 🔥
-
@dwilliamriggs
and
@foreplayzach
dropped some 💣 insights on how to think about positioning and cross-selling between
Been thinking about starting a "Diary of An Entrepreneur" series for a while & figured the best way is to just pull the trigger.
In the spirit of Building In Public, I want to start a conversation around the actual day-to-day emotional & psychological journey of being an
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155
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Leaning into the people pleaser in me was the best for launching an agency.
Killing the people pleaser in me was the best for scaling it.
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One of the best parts of an agency is seeing a LOT of ecom brands, from pre-launch to $500M+ in revenue.
We've seen which ones scale, stagnate, implode, go bankrupt & everything in between.
Here's my list of the 5 biggest "difference-makers" for long-term success 🧵
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Diary Of An Entrepreneur Series continued...
Day 59:
- Spent all day at our booth at
@CollisionHQ
for their Alpha Startup program with
@RachylNeidecker
- Not gonna lie, the introvert in me is absolutely dying right now. 10 hours straight of pitching & took a short break before
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My best advice for anyone thinking of being an entrepreneur...
Don't start a business, unless you can't NOT start a business.
Being an entrepreneur is never the "rational" move... it takes a level of irrational dedication to get through to the good part.
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I'm pretty introverted.
Humans drain me. I love 'em. But too much interaction & I'll want to hide in a cave.
But meetings, calls & relationships are part of being an entrepreneur.
Here are 6 introvert energy management tips I've learned over the years 👇
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Our new homepage for
@longplaybrands
is finally liiiiive 🥳
4 years ago, I started
@longplaybrands
to specialize in email marketing for e-commerce brands.
At the time, there weren't many email marketing agencies. As an ecommerce brand owner, you had 2 options:
1. hire a
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You're starting an agency, pick 2:
Have 2 business influencers plugging your stuff
3 big name clients to start
No pain-in-the-ass clients
5+ year LTV
Massive organic traffic source
Scalable paid acquisition channel
Team that can fulfill on work without you
50% cross-sell rate
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The one phrase that has been running through my mind non-stop for the last 30 days is...
Do. Not. Be. Out-Executed.
Vision is great, but execution is everything.
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If you want your business to grow 50% year-over-year...
It means YOU need to grow 50% year-over-year.
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How I landed 2 marketing assistant jobs at 20 (w/ no experience), got a CMO + equity offer at 20 (which I turned down) and became a CMO by age 21:
Do the work before you get the job.
Don't be scared to do work without pay or "isn't worth the effort". It's your ticket.
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I've come to the conclusion that
... I'm pretty good at being an Entrepreneur
... half decent at being a Founder
... & just now learning how to be a proper CEO.
And that they're totally different roles.
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0% of this year has gone according to plan.
But it has hands down been the best year ever.
10/10 across the board: personal, business, community, friendships, relationships...
Just goes to show, sometimes life can be better than you can imagine 😊
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I scaled
@longplaybrands
to 7-figures in its 1st year.
Then I spent the 2nd year overhauling everything.
We're coming up on year 5 soon. That's wild.
Here's the breakdown of each year in my journey of building a 7-figure agency...
The good, the bad, the ugly (a 🧵)
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Hard truth to face as an entrepreneur...
Anything you're not happy with, you created.
Don't like your team? You hired 'em
Don't like your customers? You picked 'em
Industry having a tough year? You chose it
If you're not in love with your business, it's up to you to change it.
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Diary Of An Entrepreneur Series continued...
Day 62:
- I'm reminded this week how much of business is just relationships... with partners, customers, team members etc.
- I've learned over the years that when my social battery is running super low, I start getting hyper critical
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I'm all in on playing the long game now.
I'm optimizing for an amazing 50 years, not a great 5 months.
And I want to have a f*cking amazing time along the way.
And the
#1
mantra top of mind has been...
"Slow is smooth. Smooth is fast."
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(shouldn't be that hot) take 🔥
Experience = time x depth x intensity
"25 years experience" means nothing, if I don't know the depth and intensity you worked at.
That's why 1 year of entrepreneurship can give you more experience than 20 years in a business analyst role.
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@thesamparr
@ShaanVP
I like that the only design lever pulled on this first pass is typography orientation 🤣
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I'd attribute at least 50% of my entrepreneurial success to masterminds like Baby Bathwater,
@Mastermindtalks
@HamptonFounders
&
@MavDNA
.
& I get a lot of questions from friends around how to get value out of them.
Here are my 4 tips to getting 100x ROI out of masterminds 🧵
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One of the biggest lessons I’ve learned as a leader is that you need to repeat yourself, often multiple times, in multiple different ways.
Culture is built through repetition.
Repetition in training, onboarding, 1:1s, systems, all-hands calls, & more.
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Retention marketing can get complex & overwhelming.
You gotta figure out:
- email & sms
- campaigns & flows
- tools (upsells, repeat purchase)
- programs (loyalty, affiliate, subscription)
etc.
Here's the 3-step process to quickly prioritize your retention marketing efforts 👇
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Day 1:
- Been having some minor depression the last day & really didn't want to get out of bed today
- Found myself spiraling & feeling like a failure that we don't have back to back demos lined up right at launch
- But had one demo call w/ portfolio company today that was
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The
#1
thing to know when building a new business:
It's straight up just hand-to-hand combat. Every day. Non-stop.
You gotta be willing to get your hands dirty. For at least the first little bit anyway. And it's unavoidable no matter what people say.
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What are your little day-to-day "I made it!" moments in your life?
Mine are:
1. Just ordering what I want without needing to consider the price
2. Buying cut fruit & butcher store meat
3. Everytime I walk into my condo. (It was my dream building when I was in college)
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Business Fail Story 📉
A 🧵 on how I almost tanked my agency
@longplaybrands
with a bad business model before we barely got off the ground 👇
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I basically run my life from 3 principles & it has been working great:
1. F*ck yes, or no
2. High standards, low expectations
3. Make my outsides reflect my insides (alignment)
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OK seriously. WHAT is up with Twitter's search/tagging function?
If I don't know the exact handle of whoever I'm trying to tag, it's basically impossible to find them.
Is this not irritating the crap out of anyone else?
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Entrepreneurship mostly comes down to keeping up the momentum & continually moving forward.
Even if you're crawling some days & sprinting other days.
Just keep going.
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Diary Of An Entrepreneur Series continued...
Day 276:
- Met
@AaronOrendorff
for the first time on Zoom today as we're in the middle of launching a rocket that is gonna break the DTC internet with
@AndrewDurot
🚀
- I haven't sprinted this hard than in the last 48 hours to
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The sales process isn't over just because the contract is signed.
The sales process isn't over just because the customer checked out.
Customer retention means continuing to "sell' your customer with value, support & delight -- at every stage of their customer journey.
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Me: Panic texting about the responsibilities of what being a good leader means & feeling guilty for enjoying life
@thedanielokon
: 👇
🤣 this is why I don't know how people get through entrepreneurship without the best friends
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Entrepreneurship is an art, not a science.
Marketing is an art, not a science.
Ecommerce is an art, not a science.
There is no perfect metric, formula, tactic or playbook that exists.
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Your reputation is what people say about you when you're not around.
Protect your reputation at all costs.
Not by caring what people think, but by acting in integrity even when no one's around.
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While you're building your business, don't forget that you're also building a life.
Your business is only an (important) part of a bigger thing.
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Entrepreneurship gets "easier" over time.
Not because the challenges become any easier.
But because you gain trust for the process & yourself.
Situations now that have you wondering if your business is going under...
Become natural parts of the business cycle to plan for.
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Strong opinions, loosely held
Those are my favorite types of people to be around.
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What's the appropriate amount of "business planning" a new entrepreneur should do?
And at what point does it just become a waste of time?
I'm a fan of having a super clear 6-12 month plan, and then a 5+ year direction.
Everything in between seems like it's just make believe.
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The last few months has really reminded me that I work best with my back up against the wall.
A lil' pressure is good.
Constraints create bigger thinking & unlocks a higher level of operating by necessity.
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Diary Of An Entrepreneur Series continued...
Day 150:
- damn, I've done 150 of these huh? That's pretty cool!
- Slept at midnight & body woke up at 5:30 AM just ready to go again so not sure what's up with that. Focusing on the positive side of sleepness with "getting more
5
1
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Diary Of An Entrepreneur Series continued...
Day 85:
- Wall of calls from 11 AM - 6 PM, and now prepping for the
@HamptonFounders
dinner happening in an hour at my place 🥳
- Had an awesome Audit & Strategy call & discovery call for two potential clients for
@longplaybrands
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You know Calendly is losing serious market share because people now say "Do you have a calendar link?" instead of "Send your Calendly?"
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What's the most cheap thing you'll continue doing out of principle, no matter how successful you are?
I'm gonna keep stealing hair ties from gym bathrooms until I die 😂
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Did 4 days of no food, no water recently. It was challenging & incredible.
Highly recommend. 10/10 will do again.
Did it for self-development & spiritual growth reasons, more so than the physical detox.
Here's how a 4-day dry fast made me a better leader & entrepreneur🧵
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Enough of the marketer talk...
Your Welcome Flow isn't there to "introduce or indoctrinate email subscribers to your brand".
It's to drive them to make a first purchase.
Here's what to do & not do👇
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You know how they say, "If everyone's an asshole, you're the asshole"?
Well, if you're always complaining about how much your team sucks, you suck.
Leadership is earned, not given. A team is created, not found.
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Biggest trap for new entrepreneurs?
Trying to scale too fast.
It's not just about speed.
It's about ensuring every piece of your business can handle the growth.
Sustainable growth > Speed
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If you're asking for "guaranteed ROI", you're not doing your job as an entrepreneur.
Literally the whole job is to find where to put resources when there is no guarantee of a return of investment.
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Let's talk about post-purchase nurturing for a sec.
What does "nurture" even mean?
Here are 10 tangible goals you should have for an effective post-purchase nurture strategy 👇
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THIS. If I got $1000 for every time we lost a lead during our discovery/audit process because they went with someone who did 1 call & could 10x their revenue in 90 days with a 1 week onboarding time...
Only to have them return 3-6 months later in a way worse position + now even
If a agency or vendor offers you a deal without having deep-dived into A) what you need, B) what you’re currently struggling with, and C) what business goals you’re trying to achieve.
Run away 🚩🚩🚩
Immediately
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Diary Of An Entrepreneur Series continued...
Day 174:
- Podcast episode with
@wmharris101
has dropped 🔥 Link to episode below! We covered everything from the personal to the professional, from:
1. My journey from panic attacks/anxiety to actuarial science to starting
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Diary Of An Entrepreneur Series continued...
Day 66:
- Gonna be speaking at
@affiliatesummit
east in NY July 31 - 1 🥳 who's in town?!
- Gonna be doing a talk on building & executing on the retention marketing stack DTC ecom brands need (email, sms, direct mail, subscription,
Been thinking about starting a "Diary of An Entrepreneur" series for a while & figured the best way is to just pull the trigger.
In the spirit of Building In Public, I want to start a conversation around the actual day-to-day emotional & psychological journey of being an
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At
@longplaybrands
, we've lost 6 clients in the last 9 months due to bankruptcy/going under.
With all the challenges going on in DTC, it's been a reminder that you gotta get the foundations right for sustainable, profitable, scalable growth.
It's the only way to survive.
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LIVE UPDATE:
✅ Finished recording the
@socialsnowball
course on retention strategies at each stage of your customer lifecycle
✅ Finished recording the
@LiveRecover
course on personalization & segmentation in retention marketing
✅ Cranked out a bonus course for
@amped_io
on
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A big reason entrepreneurs are unhappy, despite (or because of) their success is that they've forgotten...
That money is a means to an end.
It's a currency. It's literally useless on its own. Its usefulness comes from being traded for something else.
Peace, time, freedom,
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The Layering Approach is the way to build your Retention Ecosystem.
It's the way to scale your DTC brand to 7, 8, and 9-figures.
Methodically. Systematically. Effectively.
Here's the step-by-step breakdown on how to do it yourself (a 🧵)
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@AnthonyVicino
PEMF mat, the right desk setup (not that expensive but 🤷🏻♀️), butcher store meat
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