Entrepreneurs
How To Negotiate The Deal Of Your Life
I’m sitting at my computer looking at the email I wrote three days prior. Why is it that I can’t send it? The reason is because it’s the deal of my life. It has the capacity to shape my future and allow me to do something that will make a global impact.
The email I’m about to send only has one sentence. The sentence contains my one line reply to the offer I’m willing to accept. There is a chance I’m being too greedy, or too assertive or too whatever. That’s the risk I have to take because that’s what negotiation is all about.
I hit send on the email, and suddenly I felt a wave of relief. What made the email so hard to send was that it was going to a close friend. This meant the odds of failure became higher. It’s these new high-stake odds of failure that I now thrive on.
In the past, I would have lowered by standards or avoided confrontation, but now I’ve accepted those fears as part of the process of daily growth. Avoiding tough decisions will not make you happy; in fact, it will make you incredibly unhappy.
Getting used to the tough negotiations and the extreme stress that can come with the process is the way you become a better decision maker long term. As you become a pro decision maker, you can get yourself into powerful situations that others can only dream of.
Here is how to negotiate the major deals of your life:
1. Negotiate with yourself first
Above everything else I have mentioned, you have to negotiate with yourself first. You must know the following about yourself before you enter any negotiation:
- What value do you bring?
- What’s the minimum you are willing to accept?
- Is this your version of the deal of your life? If not, then call off the negotiation.
- What does the other side get?
- What can go wrong?
- Is this the best opportunity to achieve your dream?
Once you’ve answered these questions, you’ll be in agreement with yourself. The biggest factor in your success is you. The way you think and the negotiation you have with yourself is where all of your success will stem from. Be harsh on yourself and ask the challenging questions.
“When you’re aligned with yourself, there’s no negotiation you can’t win” – Tim Denning
2. Let the other side make an offer
When the negotiating starts, the first thing you must do is shut up and let the other side make the first offer. The first offer can often be very different from what you expect. Once the offer is out on the table, the negotiation begins, and you have the advantage.
3. Start outlandish
This is your future we’re talking about. I want you to counter the first offer with some stupidly outlandish offer. The idea in negotiating is to reach a middle ground slowly. I’ve had times where I have put a crazy offer on the table, and it’s been accepted first off.
Don’t be afraid to start big and keep your poker face on so they know you mean business.
4. Be 100% honest
Negotiation breaks down when both sides are not being honest. By being honest, you have a much greater chance of getting what you want. Everyone wants to negotiate with people that are honest. If you bullshit to people, then you will get found out, and you’ll destroy the deal of your life.
Being honest allows a negotiation to reach an outcome much sooner.
5. Talk about the fear you have
While offers are going back and forth, talk about the fears you have. Use this as leverage for the other side to reconsider their position. If they present you with their fear, counteract it with the opposite fear to their own.
Where possible, counteract their fear with a solution that makes logical sense. Then renegotiate the offer again which will put you in a much stronger position.
6. Don’t forget your value
Your value can easily be underestimated. Remember what you bring to the table and get good at summarising the key points of your value. Each time you ask for more, circle back over the value you bring before presenting your “ask.”
We all undervalue ourselves far too easily, and we’re talked down from our position. Be crystal clear on why you do what you do, and don’t be afraid to compare yourself with others. You need to speak with vision, purpose, and passion, so that your value can be highlighted.
7. Let emotion shine through
This is the deal of your life we’re talking about. This is the time to demonstrate your emotion and use it to bring everyone you’re negotiating with closer. Tell some powerful stories that set the scene for why you belong in this negotiation.
Wear your heart on your sleeve and be proud of the journey you’ve travelled to get to this point. Talk about all the growth you’ve endured to be where you are today and about the tough times you’ve gone through.
Talk about your failures as much as possible and let them be the education that allowed you to think the way you do. Your emotion is what is going to get people to side with you, and give up some of what they want, to have you take the lead.
In a negotiation, you’ll be amazed how little the other side will settle for when you allow them to experience a mixed range of emotions that end with them feeling good.
8. Show how much you want it
Don’t sit there being half-assed about why you’re there. Make sure that if there is one thing the other side knows, it’s how badly you want this opportunity. Make them understand that you will give everything you have and go broke if that’s what it’s going to take.
If you’re not prepared to say these sort of lines, then you have to ask yourself why you’re there in the first place. Everyone loves to see another human being dedicated to the cause and ready to give it their all. It’s this idea that is the cornerstone of all sport. It can help you negotiate.
9. Demonstrate confidence
Without letting your ego become inflated, be confident with who you are. Know that you’re at the negotiating table for a reason and believe in yourself. You have been picked for this opportunity because, whether you know it or not, it is part of your destiny.
Sit or stand up straight, and take action in a slow and very deliberate way.
10. Allow long pauses
The worst thing you can do in a negotiation is break long pauses of silence. The other side may be in a thought pattern that benefits you and, by you breaking that pattern, you could essentially destroy your success in the negotiation. Silence is bliss.
Silence means you’re making people think. Imagine the negotiation like a chess game. Every move is calculated. If you’re hit with a difficult question, don’t feel the need to answer right away. In fact, don’t be afraid to be excused while you think it over. You can even phone a friend if you need to.
11. Both sides need to win
What you must understand about negotiation is that deals only get done when both sides win. If you’re the only one that can win then the other side won’t agree to a position. Find a way to negotiate where you get what you want, and articulate what the other side gets that is of similar value.
I’ve seen many deals done over my time where one side gets a massively bigger win than the other. These deals don’t last, and someone always ends up breaking the contract or going back on their word.
12. Dust off the anxiety and fear
It’s a nervous thing to negotiate the deal of your life. It takes guts, and most people avoid these decisions. Not you, though. You’re braver than most. Dust off the fear which we all have, and accept that the negotiations may fail.
You’re going to sweat, your hand might shake a bit, and you might need to sit down. That’s cool. Try taking a few deep breathes and incorporate a few minutes of meditation, if you can, before the big moment. Meditation will make all the difference, keeping you cool, calm and composed.
13. Use competitive tension
In all my negotiations, I’m never scared to use leverage. The way you do this is through competitive tension. Almost always, you’ve got another deal on the table, and you need to let the people you’re negotiating with know that.
Tell them about the other offers, and then tell them how you’re prepared to forget all of them because this is the right opportunity for you. Tell them you’re having this conversation because this is the deal you want to get done, not the others. However, always mention that you’re prepared to look at the other offers in the event that an agreement can’t be reached.
This tactic works as long as you don’t come across as a smart ass. The whole idea is to create some urgency and let everyone know where they stand.
14. Cement it in writing (friends can have issues too)
Once you get the deal you’re after, get both sides to sign something so it’s official. If you walk away with no commitment and nothing in writing, you’re leaving the terms of the deal wide open for further negotiation.
Even if you’re dealing with friends and family, this rule still applies. It’s in these circumstances that you need things in writing because emotion is more likely to take over, and make you do something you’ll regret.
15. Be prepared to walk away
This one’s the scariest, but it’s a must. When you’re negotiating the deal of your life, it’s easy to fall into the trap of thinking that another opportunity won’t come around again. It will.
The mindset you need to foster is that even if you mess everything up and the deal falls through, you can always go back later and negotiate from scratch. By being prepared to walk away, you demonstrate to the people you’re negotiating with that you are serious.
The moment you’re deemed as not being serious, all your negotiating power disappears. It’s like when 99% of people are offered a pay rise or a promotion; they just accept what’s told to them. Never accept, always negotiate, and be prepared to walk away.
The result of the email was that I got what I wanted exactly and achieved slightly better results than I expected. In the process, I’ve become credible in the eyes of the other party, and we’ve both come to a position that works overall.
What’s the most critical negotiation you’ve ever been through, and how did it turn out? What did you learn in the process? Let me know on my website timdenning.net or my Facebook.
Entrepreneurs
What Risks Do Entrepreneurs Create When They Turn Personal Expertise into a Paid Service?
Businesses often begin when clients pay for existing expertise. A marketer becomes a consultant, a fitness enthusiast a coach, or a designer a freelancer. Payment creates duties that informal advice never carried. Clients can lose money, suffer injury, expose data, or challenge ownership.
The first task is to define what is being sold and what could go wrong. Suitable insurance for business should support this assessment, but a policy cannot repair unclear promises, weak records, or work performed outside the entrepreneur’s competence. The safest approach combines clear contracts, sound working methods, suitable insurance, and honest marketing.
Expertise Creates a Contractual Standard
Under the Consumer Rights Act 2015, services supplied to consumers must be performed with reasonable care and skill. This does not guarantee a perfect result. It means the provider should work to the standard expected from a competent person offering that service.
For example, a career coach cannot guarantee that a client will secure a £60,000 role. However, the coach should not rewrite a CV using false qualifications, miss agreed deadlines, or give advice without checking basic facts. Problems often begin when promotional language promises outcomes that the provider cannot control.
Entrepreneurs should state the service scope before starting work. A useful agreement should identify these points:
- The exact deliverables and number of revisions
- Deadlines and information the client must provide
- Fees, payment dates, cancellation terms, and refund rules
- Exclusions and limits on the service
Advice Can Cause Measurable Financial Loss
Professional indemnity insurance covers certain claims arising from negligent professional services or advice. It may help with legal defence costs and compensation, subject to the policy wording, limit, excess, and exclusions.
Consider a marketing consultant who schedules a retailer’s campaign after a sales event. The client claims that wasted advertising spend and lost sales resulted from the mistake. Even when the allegation is disputed, obtaining legal advice can cost money.
Common professional claim triggers can include:
- Incorrect advice, calculations, specifications, or instructions
- Missed deadlines that cause a client financial loss
- Accidental breaches of confidentiality
- Lost documents or corrupted client files
- Claims involving copyright or other intellectual property
Professional indemnity policies commonly respond only to claims made while cover is active. The policy normally needs to be in force when the claim is made, not only when the work occurred. Continuous cover and an appropriate retroactive date therefore matter when changing insurer or stopping trading.
Client Contact Creates Physical and Digital Risks
A knowledge business can still cause physical harm or property damage. A client may trip over equipment during a workshop, or a consultant may damage a computer at the client’s premises. Public liability insurance is designed for claims from members of the public connected with business activities.
Digital work creates another serious operational risk. Coaches, tutors, recruiters, and advisers may store addresses, health details, payment records, or confidential business files. Sending information to the wrong recipient, losing an unencrypted laptop, or suffering a ransomware attack can create a personal data breach. Reportable breaches must normally be reported to the Information Commissioner’s Office within 72 hours of the business becoming aware of them.
Cyber insurance may cover investigation, restoration, notification, and liability costs. Entrepreneurs should still use multifactor authentication, encrypted devices, restricted file access, secure backups, and a written breach response process.
Contracts Must Address Ownership and Responsibility
Intellectual property often causes expensive client disputes. In the UK, an independent creator usually owns the intellectual property in commissioned work unless the contract transfers those rights. Paying for a logo does not automatically settle questions about ownership, modification, resale, or portfolio use.
Contracts should specify whether the client receives ownership or a licence, when rights transfer, and whether materials from others are included. Entrepreneurs must also confirm that fonts, photographs, templates, software, music, and research can legally be used for the intended commercial purpose.
Business Structure Does Not Replace Protection
A sole trader has unlimited liability, meaning business debts are legally personal debts. A limited company is a separate legal entity, but incorporation does not remove every exposure. Directors can still face personal consequences for guarantees, unlawful conduct, regulatory failures, or their own negligent acts.
The trading structure, contract, and insurance policy should work together. Hiring staff introduces another important legal duty. Most UK employers must hold employers’ liability insurance of at least £5 million for employee injury or illness connected with work.
Checks before Accepting Paid Work
Before signing a client, an entrepreneur should:
- Confirm that the work matches their training and experience
- Record the agreed outcome, assumptions, and exclusions
- Check policy limits, excesses, activities, territories, and exclusions
- Avoid guarantees where results depend on outside factors
- Keep dated advice, approvals, revisions, and delivery records
Turning expertise into income can be rewarding, but payment changes the relationship. A dependable service needs more than talent. It requires defined boundaries, evidence of decisions, secure information handling, and insurance matched to the work being performed.
Entrepreneurs
How to Think Like a Billionaire: 7 Blueprints for Asymmetric Success
Having breakfast with billionaires isn’t just about the coffee; it’s a front-row seat to a masterclass in wealth creation. When you spend enough time around the top 0.001% of the economy, you quickly realize that their success isn’t just a byproduct of hard work or extreme intelligence. It’s the result of operating on a completely different framework than the rest of the world.
These aren’t secrets reserved for the elite. These are actionable strategies you can apply today to accelerate your own financial trajectory. Here are seven distinct ways billionaires think and act differently to achieve crazy high levels of success.
1. They Don’t Wait for Luck; They Engineer the Odds
Most people view luck as an on/off switch—you either get a lucky break or you don’t. Billionaires view luck as a dimmer switch. They understand that while you cannot control the lucky break itself, you are in complete control of the odds of it happening.
If you sit on your couch doom-scrolling, you have reduced the odds of a lucky encounter to zero. If you go to a networking event, pitch your business to a new investor, or launch a new product, you’ve instantly increased the odds of luck finding you.
Take Richard Branson. He frequently attributes his success to “lucky timing” and “lucky breaks.” But what people overlook is that Branson started over 400 companies and signed hundreds of artists to his record label. Most failed, but a few became wildly successful. He didn’t just get lucky; he put so many irons in the fire that mathematical probability guaranteed one of them would strike hot.
The Takeaway: Are you putting yourself out there enough to get lucky? Increase your pitch volume, product launches, and networking interactions to artificially inflate your odds of a lucky break.
2. They Invent Their Own Currencies
The middle class trades time for dollars, euros, or pounds. It is a very basic, low-level way to view currency. Billionaires create alternative currencies and use them as leverage.
- The Currency of Equity: If a founder sells 10% of their startup for $10 million, the entire company is now valued at $100 million. They can now use their remaining shares as a currency to acquire other businesses or attract top talent, without spending a dime of actual cash.
- The Currency of Reputation: A highly respected billionaire can join an advisory board, and their mere association will double the valuation of that company. They treat their name as currency and trade it for equity.
- The Currency of Distribution: If you have an email list of 600,000 engaged buyers, or 50,000 highly targeted LinkedIn followers, that is a currency. You can use that distribution power to negotiate equity stakes in other businesses.
3. They Reverse-Engineer the Future
Most entrepreneurs forward-engineer the past. They look at what they did yesterday to figure out what to do tomorrow. Billionaires reverse-engineer the future.
They project themselves three years forward and create a vivid, highly detailed picture of their company. They know their exact revenue, profit margins, team size, and intellectual property. Once that vision is locked in, they work backward:
- If this is true in 3 years, where must we be in 2 years?
- If that is true in 2 years, where must we be in 1 year?
- If that is true in 1 year, what must I do this week?
Because they have such a clear vision of the future, they become master storytellers. They can walk into a room, pitch an investor or a top-tier CEO, and say, “This is exactly where we will be in 36 months, and here is the exact role I want you to play.” They don’t care about their past; they only care about assembling the resources to meet their future.
4. They Are Master Enrollers, Not Doers
A great business is simply a collection of exceptional people aligned toward a common goal. Billionaires rarely do the actual “work” themselves because they understand that a single visionary cannot execute a 500-person vision alone.
Their full-time job is identifying, recruiting, enrolling, and aligning top-tier talent. As one billionaire noted, “A thousand good musicians cannot write a single symphony. But Beethoven wrote nine of them.” The difference between good talent and great talent is exponential.
Billionaires are constantly hunting for four types of people to enroll in their vision:
- Distribution Masters: People with massive audiences or traffic.
- Leadership Talent: Elite executives who can drive teams (CFOs, COOs).
- Elite Practitioners: The best-in-class engineers, sales reps, or artists.
- Capital Providers: Angel investors and VCs who can fund the vision.
5. They Harness the Dark Side of Motivation
Millionaires motivate their teams with carrots—vision boards, bonuses, and big goals. Billionaires know how to use the stick. They understand that while human beings are motivated by positive outcomes, they are ferociously driven by negative ones.
Billionaires intentionally create a common enemy to rally their team against.
- Richard Branson made British Airways the enemy.
- Steve Jobs famously made IBM the enemy in 1984.
Whether it is a rival company, an outdated political system, or a local competitor across the street, giving your team a tangible enemy to vanquish unlocks a level of gritty, relentless motivation that positive reinforcement simply cannot touch.
6. They Only Play Games of “Value at Scale”
A private tutor or a nurse provides immense value, but their impact is limited to the physical room they are in. The modern economy does not reward pure value; it only rewards value at scale.
Billionaires build systems that deliver value to millions of people simultaneously. There are four primary levers they use to achieve this scale:
- Intellectual Property: Patents, books, media rights, and franchise manuals.
- Distribution Channels: Owning retail chains, massive email lists, or media platforms.
- Armies of People: Training massive workforces to execute a standardized service globally.
- Software/Code: The ultimate scaler. Code written once can be accessed by billions of people instantly.
If your business relies on complex, bespoke solutions, it will hit a wall. Simple scales; complexity fails.
7. They Build to Exit
We often hear the romanticized stories of founders building their companies from the ground up, but we rarely hear the most important part of the billionaire playbook: The Exit Event.
Almost every ultra-wealthy individual built their fortune through a series of exits. They build a company, sell it, and take the cash.
But an exit provides something far more valuable than just liquidity—it provides time and consolidated learnings. When an entrepreneur sells a business, they clear the deck. They can look back at their 5-year journey, analyze their mistakes, and launch their next venture with capital, free time, and elite experience.
Many entrepreneurs hold onto their first business far too long. Your current business is based on the best thinking you had five years ago. An exit allows you to launch your next empire based on everything you know today.
Daniel Prestley the Aussie entrepreneur nails the top points of what makes the Top 0.1% do to be successful:
Entrepreneurs
Why Successful Entrepreneurs Break Every Rule (The 6 “Counter-Conventional” Mindsets)
In 1995, a graphic design teacher named Lynda Weinman just wanted a digital sandbox. She needed a place online where her students could upload their work and play around with new tools like Photoshop and Illustrator. She bought the domain Lynda.com, put the site together, and gradually moved her teaching online.
Years later, she sold that little digital sandbox to LinkedIn for $1.5 billion.
Or look at Elon Musk, who managed to generate half a billion dollars in cash for Tesla before a single Model 3 ever rolled off the assembly line.
How do these founders pull off such massive feats? According to John Mullins, a professor at the London Business School, successful founders don’t follow the “best practices” taught in corporate boardrooms. They operate on a completely different psychological wavelength. They possess what Mullins calls a counter-conventional mindset.
If you want to build a thriving startup in today’s fiercely competitive market, you have to unlearn corporate logic. Here are the 6 rule-breaking mindsets that will completely change how you do business.
1. Say “Yes, We Can” (Even If You Don’t Know How)
Corporate strategy 101 tells companies to “stick to their knitting” and focus entirely on their core competencies. If a customer asks for a service outside that narrow scope, the corporate answer is always, “No, we don’t do that here.”
Entrepreneurs say “yes,” and figure out the “how” later.
Arnold Correia ran a highly successful event management business in Brazil. One day, a major client asked if Arnold could build a satellite uplink to broadcast training videos to 260 stores across the country. Arnold knew absolutely nothing about satellite technology. His response? “Yes, we can do that.” Later, Walmart asked if he could put screens on their sales floors to run targeted advertisements. Again, he said yes.
By refusing to be boxed in by his current skillset, Arnold reinvented his multi-million-dollar business four separate times.
The A2S Takeaway: Don’t let your current limitations cap your growth. Commit to the opportunity first, and acquire the skills second.
2. Obsess Over Problems, Not Products
Big corporations are obsessed with product tweaks. They take the blue specks out of their laundry detergent, turn them green, and call it “breakthrough innovation.”
Entrepreneurs don’t care about shiny products; they care about solving painful problems.
Jonathan Thorne invented a silver-nickel alloy for surgical forceps to stop human tissue from sticking to the metal during surgery. He originally targeted plastic surgeons, but sales were sluggish. Instead of changing his product, he looked for a worse problem. He found neurosurgeons. When you are operating on a human brain, sticky forceps are a literal life-or-death disaster. Thorne targeted this massive pain point, scaled his business rapidly, and eventually sold it to medical giant Stryker.
The A2S Takeaway: Nobody cares about your shiny new product features. They care about their own headaches. Find a bleeding-neck problem, and cure it.
3. Think Narrow, Not Broad
Corporate giants want massive total addressable markets (TAM). If a market doesn’t appeal to the masses, they won’t touch it. But true entrepreneurs know that to go big, you have to start narrow.
When Phil Knight and Bill Bowerman founded Nike, they didn’t try to make sneakers for the general public. They focused on a tiny, extremely specific niche: elite distance runners. At the time, running shoes were made for sprinters on smooth tracks, leaving marathoners to deal with sprained ankles and shin splints on dirt trails. By designing a wider, cushioned shoe exclusively for distance runners, Nike built a rabid, hyper-loyal fan base that eventually gave them the leverage to conquer the global athletic footwear market.
The A2S Takeaway: Niche down until it hurts. Dominate a small group of highly passionate users before you try to sell to the world.
4. Ask for the Cash Upfront (Ride the Float)
Big companies have billions in cash reserves to fund their R&D. Startups don’t. But instead of begging venture capitalists for money, brilliant entrepreneurs get their customers to fund their operations.
When Elon Musk took over Tesla, the plan wasn’t to take on massive debt to build a factory. Instead, they hosted a roadshow for wealthy, eco-conscious buyers who wanted the “next big thing” in their driveways. Tesla pre-sold 100 Roadsters for $100,000 each. That meant they had $10 million in cash sitting in the bank before car #1 was even built. Years later, they did the exact same thing with the Model 3, taking 500,000 deposits of $1,000 each—generating half a billion dollars in pure cash to fund their engineering and tooling.
The A2S Takeaway: Cash is the lifeblood of your startup. Can you pre-sell your idea and get paid before you build it?
5. Beg and Borrow (But Please Don’t Steal)
In business school, you are taught to carefully analyze the ROI of buying heavy assets. Entrepreneurs operate differently: they don’t buy assets if they can borrow them.
When Tristram and Rebecca Mayhew wanted to start Go Ape, a treetop adventure business in the UK, they had a major problem: they didn’t own a forest. Instead of buying land, they approached the UK Forestry Commission, which owned millions of trees and desperately wanted to increase park visitor counts. The Mayhews pitched a win-win partnership: let us use your trees, parking lots, and bathrooms, and we’ll bring you massive foot traffic. Today, Go Ape has dozens of locations globally, all because they leveraged assets that already existed.
The A2S Takeaway: You don’t need to own everything to monetize it. Partner up, leverage existing infrastructure, and keep your startup overhead near zero.
6. Don’t Ask for Permission (Just Get On With It)
In the corporate world, every new idea has to be sanitized by compliance, legal, and HR. Getting a “yes” takes months.
Entrepreneurs understand that permission is the enemy of progress. When Travis Kalanick and Garrett Camp founded Uber, they didn’t go to the San Francisco transit regulators and ask, “Excuse me, can we start a taxi company with zero actual taxis?” The regulators would have crushed them immediately to protect the local monopoly. Instead, they just launched the app. While some of Uber’s later corporate tactics crossed ethical lines, the core lesson of their launch is undeniable: when digital innovation outpaces slow, ambiguous regulations, you can’t wait for a green light.
The A2S Takeaway: If you wait for permission from the gatekeepers, you’ll be waiting forever. Act first, apologize later.
Are You Playing By The Right Rules?
To change the world—or even just your own financial future—you have to break the conventional norms. You don’t need a perfectly polished product, infinite VC funding, or permission from the establishment.
Look at the biggest roadblock in front of your business today. Which of these 6 counter-conventional mindsets can you adopt to smash right through it?
Stop waiting. Get out there and just get on with it.
Entrepreneurs
How Lucy Guo Built a Billion-Dollar Tech Empire By Breaking All the Rules
At an age when most people are just trying to figure out their career path, Lucy Guo unseated Taylor Swift as the world’s youngest self-made female billionaire.
She co-founded Scale AI (recently valued at a staggering $25 billion), launched the creator monetization platform Passes, and became a relentless angel investor with a portfolio of over 100 companies. But her path wasn’t paved with perfect grades and safe corporate ladders. It was paved with rebellion.
Guo got suspended in kindergarten for telling the teacher the curriculum was dumb. She dropped out of Carnegie Mellon University with only four classes left to graduate. She walked away from millions of dollars in unvested equity at Snapchat. Every time society told her to play it safe, she did the exact opposite.
If you want to scale a massive business and operate at the top 1% of the tech world, here is the unfiltered playbook from one of the most prolific founders of our generation.
1. Optimize for Learning Over Stability
Most people make career decisions based on risk and salary. Guo makes decisions based on a single metric: Am I maximizing my learning?
When she was a year away from graduating with a computer science degree from Carnegie Mellon, she realized she was learning more practical skills at weekend hackathons than in the classroom. So, she dropped out to dive headfirst into the startup world. Everyone—her parents, her friends, even strangers—called her an idiot.
Later, she walked away from a highly lucrative position at Snapchat to build her own company. To the outside world, these look like massive, irresponsible risks. To Guo, the math was simple: if a decision guarantees you will acquire highly valuable new knowledge, it is not a risk. Your knowledge will always be worth money.
2. The “Three-Task” Founder Routine
It is incredibly easy for founders to get distracted by busywork. Guo subscribes to the famous Y Combinator philosophy that a founder should only be doing three things:
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Working out
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Talking to customers
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Building the product
Her daily routine is brutally efficient. She wakes up at 5:30 AM, rolls out of bed, and immediately goes to a grueling fitness class. She bought her house specifically because it was a 5-minute walk from the gym and a 5-minute walk from the office, entirely eliminating her commute.
By refusing to sit still—cutting out TikTok scrolling, TV, and aimless internet browsing—she funnels all of her energy into execution. Working out tests your discipline; if you can force yourself to train when you feel terrible, you will have the energy to dominate your industry for the rest of the day.
3. Ship at 90% (The Innovation Rule)
When Guo worked at Snapchat, she learned a massive lesson from CEO Evan Spiegel about product development: stop agonizing over user research and just get the product into the wild.
If you spend three years going back and forth on a design trying to make it perfect, you will lose. The market moves too fast, and frankly, consumers rarely know what they actually want until they can touch it.
The rule is simple: Get it to 90% and ship it. Spend two weeks designing it, launch it, and see if it gets traction. People will eagerly use a buggy product with a terrible user interface if it actually solves their problem. If it gets traction, double down and fix the bugs. If it falls flat, you only wasted two weeks instead of two years.
4. Never Outgrow the “Grunt Work”
As companies scale, many founders retreat to their corner offices and stop doing Individual Contributor (IC) work. Guo believes this is a fatal leadership flaw.
You cannot effectively judge your team’s performance if you refuse to do the job yourself. When Scale AI landed a massive new pilot customer, Guo didn’t just delegate the work—she sat in the war room alongside her engineers, manually labeling data to ensure it was perfect. If a creator finds a bug at 2:00 AM on Passes, she and her team are awake fixing it.
As a leader, nothing is below you. If you aren’t willing to jump into the trenches and handle customer support tickets yourself, you have no right to critique how your reps are handling them.
5. Hire for Grit Over Pure Genius
When building a team, pure intelligence is heavily overrated if it isn’t backed by relentless hard work.
You can hire the smartest engineer on the planet, but if they refuse to put in the effort when things get difficult, they will have zero impact on the company. Guo explicitly hires for grit. Startup culture requires a 24/7 mentality. You don’t necessarily have to work every weekend, but when the building is on fire, the team needs to know you will show up and grab a bucket.
6. Stop Complaining and Start Cheerleading
When asked what advice she would give her 20-year-old self, Guo’s answer had nothing to do with code, venture capital, or marketing.
“I would stop complaining about some of the people I work with and just start really getting to know them better and uplifting them.”
Toxic, gossipy work environments drive away top talent. The most profitable and innovative companies are built in positive environments where the leader acts as the ultimate cheerleader.
Surround yourself with wildly positive people, focus intensely on the upside, and relentlessly uplift the people building your vision. When you protect your energy and support your team, the financial success becomes a natural byproduct.
Here’s a great interview with Lucy Guo:
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