50 Best Tweets About Entrepreneurship (2026)

Explore the best tweets about entrepreneurship, covering ideas, execution, customers, risk, resilience, hiring, capital, and lessons from building companies.

Firsthand entrepreneurship lessons about customers, execution, risk, teams, capital, failure, and building durable businesses.

Creators
44
Updated

What 50 top Entrepreneurship posts reveal

The evidence frames entrepreneurship as a trade-off between autonomy and uncertainty. Customer orientation, focused execution, incremental progress, and risk tolerance are recurring lessons. Posts about AI commonly describe faster, cheaper building alongside intensified competition and a continued need for customer understanding and sound judgment. The evidence also presents a tension between long-term company commitment and low-cost experimentation.

Dominant tone
Positive

50% of posts

Median score
19.9

All-time engagement

Leading format
Announcement

66% of posts

Recent posts
48%

Published in 90 days

Conversation map

The themes creators return to

Founder psychology and resilience

The emotional demands of entrepreneurship: independence, uncertainty, sacrifice, discipline, endurance, meaning, and learning to perform through pain and volatility.

40%

Execution focus and iteration

Making decisions quickly, avoiding tool paralysis, prioritizing the highest-leverage problem, building systems, and compounding small wins through consistent action.

32%

Risk, capital, and ownership

The trade-off between entrepreneurial upside and downside, financial volatility, runway, debt, VC versus profitability, and wealth created through ownership or exits.

22%

Idea selection and business strategy

Choosing markets, finding differentiated angles, pursuing latent demand, balancing innovation with proven models, and designing businesses for durable economics.

20%

Hiring, teams, and leadership

Selecting early talent, developing culture, delegating, managing growing organizations, leading through setbacks, and bringing people around a mission.

18%

AI-enabled entrepreneurship

How AI lowers startup costs and accelerates building while increasing competition, shortening product cycles, and changing the viability of solo companies.

14%

Tone and stance

Sentiment Positive leads
Author posture Supportive leads

Performance benchmark

Median likes
60
Median reposts
6
Median replies
8
Median views
4.7K

Posts with media make up 46% of this collection. Their median all-time score is 15.6, compared with 23.9 for text-only posts.

Format mix

  • Announcement 66% · score 17.7
  • List 16% · score 71.3
  • Story 16% · score 10.8
  • Question 2% · score 68.0

Where creators agree, and where they do not

Shared view

Focused execution and incremental progress are recurring advice

Posts emphasize choosing the highest-priority problem, making decisions rather than remaining stuck, and pursuing achievable milestones that can build momentum over time.

Shared view

AI may accelerate building without removing business challenges

Posts describe AI as lowering barriers to creating products and enabling faster work, while arguing that customer conversations, decision quality, and differentiation remain important in more competitive markets.

Open debate

Long-term company commitment versus frequent low-cost bets

One post favors pursuing customer-focused, mission-driven work, while another argues that AI can make a portfolio of inexpensive, short-lived bets rational. A third advocates operating a proven model consistently over time.

Open debate

Reinventing markets versus operating proven models

One post distinguishes very large ambitions from selling into latent demand, while another advises choosing a favorable existing business model and operating it better than competitors.

Open debate

Solo building versus building with teams

Some posts present bootstrapped solo companies as increasingly viable with AI. Another argues that durable, large-scale impact still requires the ability to bring aligned people into the organization.

Patterns behind standout posts

Customer and strategy themes had comparatively high supplied medians

The supplied theme analytics report median all-time scores of 50.697 for customer discovery and market validation and 55.7 for idea selection and business strategy.

Text posts had a higher supplied median score than media posts

The supplied analytics report a text median all-time score of 23.927, versus 15.613 for media posts. Media appeared in 23 of 50 posts, or 46%.

Statistical standouts

  1. View standout post 1 Score 573.4 · 28.81× median
  2. View standout post 2 Score 419.2 · 21.07× median
  3. View standout post 3 Score 397.9 · 19.99× median
  4. View standout post 4 Score 220.2 · 11.07× median
  5. View standout post 5 Score 217.6 · 10.93× median

Who shapes this conversation

The five most represented creators account for 20% of the selected posts.

  1. 1. Big Brain Business

    @BigBrainBizness

    2 posts

  2. 2. Dilip Kumar

    @kmr_dilip

    2 posts

  3. 3. Nicolas Cole 🚢👻

    @Nicolascole77

    2 posts

  4. 4. Startup Archive

    @StartupArchive_

    2 posts

  5. 5. Nick Huber

    @sweatystartup

    2 posts

  6. 6. Sylvia

    @sylviahchannel

    2 posts

The conversation is distributed across many creators

The evidence set contains 50 tweets from 44 creators. The supplied analytics report a 20% top-five placement share.

Cited creator posts span principles, operating advice, and personal accounts

The selected posts include founder-selection criteria, customer-focused strategy, an account of incremental company building, and a personal account of business setbacks and recovery.

Firsthand accounts supply concrete entrepreneurial situations

Personal accounts in the evidence describe debt and a failed product, client concentration and team leadership during a loss, and the operational challenges that emerged during rapid growth.

Since the previous snapshot

What changed since Aug 12, 2026

  • 80% of the selected posts remained.
  • The creator count changed by -1.
  • The leading sentiment remained stable.
How this analysis was made

Themes, sentiment, stance, and post format are classified per tweet. All counts, shares, medians, creator concentration, freshness, and performance comparisons are then calculated directly from the published snapshot.

Xholic's all-time score compares engagement while accounting for reach, post age, and creator consistency. It is used for relative comparisons within this collection.

This report analyzes the exact 50-post snapshot shown below. AI identifies editorial categories and drafts explanations; all statistics are calculated from the snapshot, and every narrative claim is checked against cited posts before publication.

Top Entrepreneurship tweets from 44 creators

Ranked 01–50

  1. 01

    @kmr_dilip ·

    Entrepreneurship only makes sense if is you are unusually independent and can tolerate long stretches of irrelevance. You don’t need permission, praise, or certainty and you would regret not trying more than failing. Otherwise, the rational move is to work with talented people,

    • 102 Replies
    • 266 Reposts
    • 1.9K Likes
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  2. 02

    @ruchirjajoo ·

    While growing Amazon from $1M to $1.6 trillion, Jeff Bezos wrote 23 letters to shareholders spelling out his plan each year. I printed and read them. In them, he wrote 'Amazon' only 430 times but 'Customer' 506 times. Nothing has changed my view of entrepreneurship more...

    • 44 Replies
    • 211 Reposts
    • 2.3K Likes
    • 556K Views
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  3. 03

    @aporia9n ·

    Gen Z entrepreneurship increasingly looks like running a portfolio of asymmetric coups rather than betting everything on one serious, long-term project. One month it’s an AI wrapper. Then a TikTok Shop product, a viral food trend, or buying scarce inventory during a shortage and

    • 46 Replies
    • 89 Reposts
    • 1.8K Likes
    • 623.4K Views
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  4. 04

    @Tancrededib ·

    Early founder signals I trust more than resumes S tier: >gets in rooms they weren't invited to >fails often but wins big >people follow them without a title >has a weird specific obsession nobody else has A tier: >builds for fun >sold stuff online >creates > consumes

    • 30 Replies
    • 23 Reposts
    • 481 Likes
    • 37K Views
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  5. 05

    @StartupArchive_ ·

    Jeff Bezos’s two pieces of advice for aspiring entrepreneurs “The advice that I would give entrepreneurs is don't chase the hot new thing. It's so hard to catch something that everybody already knows is hot. Instead, position yourself and wait for the wave to come to you.” The

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    • 27 Replies
    • 80 Reposts
    • 584 Likes
    • 61.2K Views
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  6. 06

    @Founder_Mode_ ·

    This 2003 Stanford lecture by Elon Musk will teach you more about business than a 2-year MBA program: Key Takeaways: 1. Viral marketing was critical to PayPal’s explosive growth, showing the power of customer-driven referrals without traditional advertising. 2. SpaceX’s

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    • 5 Replies
    • 106 Reposts
    • 385 Likes
    • 41.1K Views
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  7. 07

    @gregisenberg ·

    I actually think the whole "permanent underclass" narrative is wrong. I think we're about to see the largest EXPLOSION of entrepreneurship in human history. I get why the fear exists. Jobs are getting cut. AI researchers are privately saying most people are screwed. The models

    • 223 Replies
    • 62 Reposts
    • 673 Likes
    • 60.9K Views
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  8. 08

    @thisisgrantlee ·

    Stripe is worth $159 billion now. Like Bezos and Buffett, the Collison 'way of building a business' will create trillions in value and is worth studying. 800-word post on: 1. Craft & Beauty 2. Humility 3. Hiring 4. Culture 5. Decisions 1. On craft & beauty, You can work on

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    • 103 Replies
    • 129 Reposts
    • 971 Likes
    • 1.1M Views
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  9. 09

    @Codie_Sanchez ·

    Hard truth: Quitting your job to go all in on entrepreneurship is in most cases dumb. • 50% of startups don't make money for the first 3 to 5 years • 34% of entrepreneurs make less than $50k a year • Only 9% of businesses hit $1M in revenue It's perfectly fine to work for

    • 151 Replies
    • 93 Reposts
    • 1K Likes
    • 117.3K Views
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  10. 10

    @StartupArchive_ ·

    Paul Graham on how to get startup ideas “The way to get startup ideas is not to try to think of startup ideas… The way to come up with good startup ideas is to take a step back. Instead of trying to make a conscious effort to think of startup ideas, turn your brain into the type

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    • 4 Replies
    • 29 Reposts
    • 216 Likes
    • 14.7K Views
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  11. 11

    @wickedguro ·

    > Age 21, released from the army, got a job building WordPress websites at $2,025 per month. > Age 23, moved to another job with a higher salary, working with PHP and Laravel at $3,037. > Age 25, moved to another job working as a dev team leader with JS, routing-controllers,

    • 93 Replies
    • 6 Reposts
    • 483 Likes
    • 36.6K Views
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  12. 12

    @andruyeung ·

    There’s an emerging wave of solo entrepreneurs who are building $100k - $1m software businesses. No VC raised, completely bootstrapped, often starting on the side while they’re still employed. The old path to building consumer businesses used to be to identify demand first by

    • 104 Replies
    • 28 Reposts
    • 312 Likes
    • 18K Views
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  13. 13

    @BoringBiz_ ·

    I genuinely wish more people understood what they were getting themselves into when they set grand ambitions for their life Being a successful business owner or entrepreneur sounds glamorous until you realize just how painful the process is Instead of having one boss, you

    • 28 Replies
    • 33 Reposts
    • 510 Likes
    • 30.1K Views
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  14. 14

    @jayvraavi ·

    i made a 2M user / $2M ARR social app as a first time bootstrapped solo founder they told me first time founders never succeed they told me social apps are tarpit ideas they told me i needed a non-tech cofounder they told me i needed to raise but there are no rules in

    • 42 Replies
    • 7 Reposts
    • 336 Likes
    • 15.5K Views
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  15. 15

    @frederickjames ·

    $15,000 in 77 days. Here's 23 things I've learnt: 1. Achieving this makes you scared of losing it. 2. Sleep, diet & exercise are more important. 3. Need emotional self regulation $500/day spend. 4. Paid ads are indistinguishable from gambling. 5. Do not prioritise profit at

    • 33 Replies
    • 4 Reposts
    • 157 Likes
    • 7.6K Views
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  16. 16

    @kmr_dilip ·

    There’s a strange problem in entrepreneurship that people who’ve never built anything feel very confident telling founders what to do. Most advice comes from people who haven’t earned the right to do that. They haven’t failed or risked their savings. Never hired or fired, never

    • 43 Replies
    • 33 Reposts
    • 335 Likes
    • 19.6K Views
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  17. 17

    @emollick ·

    Math gets a lot of attention for its unsolved problems, but there unresolved & important problems in many fields that could potentially be addressed empirically, if AI truly got good enough. Problems that, if solved, would bring large value to society. For example, I study

    • 51 Replies
    • 25 Reposts
    • 386 Likes
    • 39.7K Views
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  18. 18

    @JamesonCamp ·

    If you want to build a $100B company you need to reinvent the wheel If you want to build a $10M company you need to sell into latent demand For 99% of businesses the formula is embarrassingly obvious, but the execution breaks most people 1. Find a validated market Look for

    • 18 Replies
    • 6 Reposts
    • 164 Likes
    • 15.5K Views
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  19. 19

    @BigBrainBizness ·

    Kevin O'Leary on why hunger for money is a guaranteed path to failure: He sold his company, The Learning Company, for $4.2 billion and the morning after, he went straight back to work. As one of the founding members with founders shares, the night before closing one of the

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    • 10 Replies
    • 39 Reposts
    • 200 Likes
    • 40.8K Views
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  20. 20

    @lukaivicev ·

    Here are the most important books for company building. I spend 1h every morning reading. Reading is equivalent to working and it’s also the cheapest advice you can get from those who have done it. Many of the books/articles/blogs I’m recommending are not business orientated.

    • 3 Replies
    • 4 Reposts
    • 44 Likes
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  21. 21

    @BigBrainBizness ·

    Philosopher Jonathan Bi on the dark motivations that actually drive the world's greatest entrepreneurs: He identifies three types of people who make up the best of them: those driven by autism, megalomania, and revenge. "The best parts of society are built by the worst parts of

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    • 5 Replies
    • 7 Reposts
    • 53 Likes
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  22. 22

    @gkbalogs ·

    One of the best things that happened to me as an entrepreneur was working a 9–5. I imported the structure, order, and lessons from that experience into my business from day 1. From the very first draft of our employment letter (even though my first employee lived in my house, she

    • 2 Replies
    • 21 Reposts
    • 57 Likes
    • 1.7K Views
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  23. 23

    @galileowilson ·

    entrepreneurship at the top level is basically champions league. when you actually start doing good numbers, building out a team, having something to lose, the whole game changes. every other founder/company in your space turns into a club coming for your position. they watch

    • 14 Replies
    • 2 Reposts
    • 152 Likes
    • 3.8K Views
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  24. 24

    @sweatystartup ·

    Stop buying into the hype that you MUST invent something new. Success in entrepreneurship isn’t that complicated. Pick a good business model with favorable odds, low risk and moderate rewards. Don't innovate. Just operate a little bit better than the competition. Don’t master

    • 27 Replies
    • 6 Reposts
    • 103 Likes
    • 8.9K Views
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  25. 25

    @sweatystartup ·

    Trying to go big in entrepreneurship with zero experience, zero capital and zero network is one of the best ways to end up with a JOB! Let me tell you a secret: You have to crawl before you can walk and eventually run. Business is all about momentum. If you set big, exciting,

    • 23 Replies
    • 12 Reposts
    • 98 Likes
    • 14K Views
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  26. 26

    @Nicolascole77 ·

    entrepreneurship is the daily challenge of realizing there are 100 things broken inside your business, but you can only fix 1 at a time, which means building the skill of applying focused effort wherever it matters most without getting distracted by the other 99 fires

    • 23 Replies
    • 3 Reposts
    • 53 Likes
    • 1.6K Views
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  27. 27

    @deedydas ·

    This man dropped out of high school in Ukraine, taught himself English, forced his way into America and started 2 huge companies by 33. Here's the incredibly inspirational never-before-shared story of my friend, Dan Mishin: > be me > 11yo Ukrainian kid > family trip to Europe,

    • 14 Replies
    • 13 Reposts
    • 220 Likes
    • 23.7K Views
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  28. 28

    @dan__rosenthal ·

    In just 1 month, my co-founder and I 2X'd our business. We: - Went from 0→17 full time team members - Are working with multiple YC-backed companies. - Signed our first Fortune 500 client in February. These things are all great... But nobody tells you about the sh*tty part of

    • 5 Replies
    • 1 Reposts
    • 16 Likes
    • 796 Views
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  29. 29

    @AdewaleYusuf_ ·

    I did a personal wealth audit recently, and I realized something uncomfortable: many founders will never become wealthy, not because they failed, but because they chased the wrong goal. Somewhere along the way, we started believing that entrepreneurship only counts if you’re

    • 7 Replies
    • 4 Reposts
    • 39 Likes
    • 1.2K Views
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  30. 30

    @Nicolascole77 ·

    You can't have upside without volatility. The reason most jobs don't have upside is because they don't have volatility. That's the trade. You make "less" because what you make is consistent. If you want to make more, you have to build the skill of managing your own psychology

    • 21 Replies
    • 1 Reposts
    • 39 Likes
    • 1.9K Views
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  31. 31

    @Clara_Gold ·

    I’ve done a lot Ayahuasca. I’ve done a lot of 5-MeO-DMT. But nothing has taught me more about who I am than entrepreneurship. Being a founder drags you to the bottom of your soul. You question who you are, who you trust, what you actually care about, what you can endure. You

    • 8 Replies
    • 0 Reposts
    • 63 Likes
    • 10K Views
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  32. 32

    @aaditsh ·

    The fact that YC and Jensen can fill an arena with 6,000 ambitious founders is getting me so freaking pumped. I truly feel like it's the best time to build a company today. AI is levelling the playing ground. You can build faster than ever. You can also build the wrong stuff

    • 12 Replies
    • 5 Reposts
    • 88 Likes
    • 17.1K Views
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  33. 33

    @richardker ·

    Entrepreneurship is restraint and delayed gratification. It’s the part no one talked about. It’s when clients don’t pay on time, but your team still needs to be paid. It’s showing up after a slow week, a quiet month or a plan that didn’t work. Every day, you wake up knowing

    • 4 Replies
    • 12 Reposts
    • 28 Likes
    • 2K Views
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  34. 34

    @maruthisandeep ·

    Sent the below note to my team in December after spending 2 weeks in SF. Sharing it here as it is still true after a quarter of the year in 2026. ——— hey all concluded my 2 weeks in San Francisco, here are few things I have observed & learned: Company building: 1. The company

    • 2 Replies
    • 3 Reposts
    • 18 Likes
    • 2.3K Views
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  35. 35

    @rohanpaul_ai ·

    Why Jensen Huang would choose not to start a company if he had to relive the whole journey “Building a company and building NVIDIA turned out to have been a million times harder than any of us expected it to be. And at the time, if we realized the pain and suffering and just how

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    • 6 Replies
    • 3 Reposts
    • 31 Likes
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  36. 36

    @SergeGatari ·

    Yesterday I talked about the sales mechanism that lets me collapse time. Before I get into the how, I want you to internalize the why. So let me ask you this: why aren't you able to make 10 times more money today, this week, this month? Let me guess. It's because your entire

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    • 4 Replies
    • 0 Reposts
    • 9 Likes
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  37. 37

    @Bill_Gross ·

    What was I thinking? 30 years ago this week I started a “1-year experiment” to build a startup factory based loosely on Thomas Edison’s laboratory in Menlo Park, New Jersey. It was early 1996 and the Internet was growing like crazy after the Netscape IPO, with a whopping 30

    • 7 Replies
    • 6 Reposts
    • 35 Likes
    • 3.7K Views
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  38. 38

    @siddharthwv ·

    Underrated entrepreneurship lesson: Market before you start building. If no one cares, you just saved yourself 6 months.

    • 4 Replies
    • 0 Reposts
    • 7 Likes
    • 47 Views
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  39. 39

    @tannerdripjobs ·

    There are two types of business owners that I've come across: The first type is the ones that are constantly complaining and always looking at cost instead of value. Their first question whenever presented with something new is, "How much is it going to cost me?" Or, "How much

    • 1 Replies
    • 0 Reposts
    • 13 Likes
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  40. 40

    @remoteoliver ·

    Legit think gaming helped me to make my first $1m (I'll have to tell my parents the xbox phase was worth it) Because when I was younger I genuinely thought I was going to be a professional gamer. I'd spend weeks going all in on the sticks.. watching videos, playing in

    • 2 Replies
    • 0 Reposts
    • 15 Likes
    • 631 Views
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  41. 41

    @rohitdotmittal ·

    The United States has entrepreneurship on a scale unlike anywhere else in the world. It's so exceptionally high that we often fail to appreciate just how rare and powerful it is. Because we see entrepreneurs and builders deliver massive wins decade after decade, we forget how

    • 2 Replies
    • 1 Reposts
    • 10 Likes
    • 384 Views
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  42. 42

    @heystevetan ·

    Tool paralysis is the greatest enemy of founders of our time. It's the business equivalent of gear acquisition syndrome. It's like falling in love with running, but even before you ever go on a light stroll, you spend your entire time debating which is the best shoe to buy.

    • 0 Replies
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    • 13 Likes
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  43. 43

    @7Saturdaysaweek ·

    4 years ago, I launched 7 Saturdays Financial. That's about as long as a college degree takes. But running a business taught me things no classroom could. How it's going: Growth has been excellent. We're nearing capacity, with room for only 8 more clients. And that's forcing

    • 1 Replies
    • 0 Reposts
    • 12 Likes
    • 815 Views
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  44. 44

    @MikeHoffmann ·

    1.6M people just saw my Mike Leach post. Most of you don’t know me. Here’s the short version: - I started my career as a college strength and conditioning coach. Loved the guys/work. Hated the pay. - Got my first rental while coaching - Couldn’t afford 20% down on every

    • 1 Replies
    • 2 Reposts
    • 19 Likes
    • 4K Views
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  45. 45

    @sylviahchannel ·

    One of the big ideas from the popular business book The Lean Startup by Eric Ries is that your first product should help you learn, not simply prove your original idea was right 💨 Many founders keep adding features and polishing the design before real customers interact with it.

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    • 4 Reposts
    • 14 Likes
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  46. 46

    @sylviahchannel ·

    For the employee-turned-entrepreneurs, entrepreneurship does not just place you in the same game with more responsibility. It places you in a different commercial game altogether 🤯 👇 Inside this week's article - https://t.co/7fglY4sjxJ, I break down: → Why you can be highly

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  47. 47

    @thefernandocz ·

    This completely changed the way I think about scaling businesses... It takes the same amount of effort to build a 1x multiple business as it does to build a 50x multiple one... Some businesses trade at 1x gross revenue, some trade at 5x, and some trade at 40 or even 50x. The

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  48. 48

    @jspujji ·

    We were spending $75M a year for our biggest client when they called and told us "We don't need you anymore". At my first business Ampush, Uber was 20% of our business. One day they called and said they loved the work, but they were big enough to take it in-house. I got the

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  49. 49

    @H0wie_Xu ·

    "If you want to go fast, go alone. If you want to go far, go together." AI is rewriting this ancient wisdom however. Garry Tan, CEO of @ycombinator, said on March 29 that "The unit of software production has changed from team-years to founder-days." Garry is basically saying

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  50. 50

    @theraleighwill ·

    We all love origin stories. Go to dinner with a new couple and you ask “how did y’all meet?” Listen to an entrepreneurial podcast and it’s all about how the idea first came into being The problem in entrepreneurship is that the financial and lifestyle freedom we all want has

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