How To Play To Win | Alex & Leila Answer Your Questions Live
In a Nutshell
The core message is that most entrepreneurs play to play rather than play to win—they create excuses and acceptable failure instead of obsessively solving their single constraint with ten different approaches. Winners identify the bottleneck limiting their business, then apply disproportionate effort and volume toward that one thing until it breaks, rather than spreading effort evenly or defaulting to comfortable activities. Success requires accepting that no one cares about your excuses—only results matter—and being willing to make bigger bets, increase violence of effort, and focus aggression on the constraint rather than what feels good.
These notes were generated by AI and may contain inaccuracies.
Many entrepreneurs do not play to win. They play to tell themselves they are playing, giving themselves an excuse and reason to make failing acceptable.
A friend played for Don Shula, the famous football coach. What was interesting about playing for Don Shula compared to any other coach was that every single play in the playbook had a way of becoming a touchdown. When thinking about business moves, the question becomes whether every move ultimately helps accomplish overall goals, rather than just moving the ball forward. There is value in consistent yardage, but there are times when big moves must be made.
Small business owners have limited resources, requiring bets that have the highest risk-adjusted return. The goal is to move the ball forward the most for the least effort, repeated over time. Unlike football, business has unlimited downs but limited energy to execute them.
When entrepreneurs claim they cannot grow their HVAC business without hiring more tradesmen, they often have done only one or two things to solve the problem. The response reveals they have not hired headhunters, gone into forums for tradesmen, offered relocation bonuses, looked at poaching from competitors, run ads, attended trade shows and conferences, or established agreements with trade schools for internships.
People who want to win do not have just one way to win. The approach is to identify the single constraint limiting the business, then solve it 10 different ways. This reconciles the apparent contradiction between "do more" and "do less" - the constraint is singular, but the methods to solve it are multiple.
The constraint represents a bottleneck in the business, whether needing more leads, converting more leads, or having more delivery capacity. Once clear on the constraint, the vast majority of time should be dedicated toward that one thing. The analogy involves a piece of paper that must be burned through. The sun's energy alone will not work, but focusing it through a magnifying glass will burn through the paper. This represents focusing aggression, violence, and unreasonable action on the single constraint.
Many entrepreneurs play so they can have excuses to tell their spouses and others that they are fighting the good fight and trying hard, but it is not easy. The reality is that no one cares. At the end of the day, either you won or you did not. No one remembers how tough the referee's calls were, what the weather was like, if it was windy, if the gloves were wrong, or if there was tendonitis. People remember only who won the game.
The question is whether you are turbo bombing the constraint. For needing more tradesmen, seven different approaches can be employed. For needing more leads, options include going to trade shows, finding affiliates who already have customers, running ads on different platforms, making content on different platforms, and more content overall.
When the constraint is identified, the vast majority of time must be dedicated toward that one thing. Under one million dollars per year, focus on one thing and go aggressive with volume. If making content, make a large amount of content. If doing ads, make a large amount of ads. If doing outreach, do a large amount of outreach and stay specific on that channel.
At ten million dollars, the same level of effort used to reach one million will not reach thirty million. Adding one million dollars in revenue at ten million represents only ten percent growth. To go from ten to thirty million requires changing the leverage, which means increasing the amount of violence employed and the bet size.
If accustomed to spending one thousand dollars a day on ads to reach one million dollars, that bet size must be demolished to reach higher levels. Spending ten thousand dollars a day on ads requires making more creative, making better creative, and cracking different platforms. The constraint represents the point in the business where the highest returns on effort are achieved.
The constraint is typically not the place you like most or are most comfortable. The part of the business you enjoy most is probably not the limiter because you already work on it when having fun. At some point, the weak link becomes so weak that it does not matter how strong the strong links are.
If only one person is selling, only so many sales calls can be taken. If only one channel exists in a local business, only so many people are searching for that service locally. Another way to generate leads must be found.
A significantly larger level of violence with effort must be directed toward accomplishing the objective. Play to win, not play to play. Playing to play is acceptable if enjoying the game, but winning also brings enjoyment, and wins can make playing easier.
The question is whether you are playing to win, turbo bombing the constraint, figuring out the one thing limiting the business and then finding ten ways to win, and finding ten different ways to score a touchdown. While attribution is useful to know what worked, it is better to know that something worked rather than why it worked.
To get cheaper leads, options include changing the offer, improving the landing page, improving the quality of creative, improving the messaging, and improving the targeting on ads. When wanting to become more efficient over time, one approach can be peeled back to see if anything changes, then resources can be trimmed and redeployed.
When having conversations with founders and entrepreneurs, it is more common that they are not trialing nearly hard enough, not doing nearly enough volume, and not playing to win.
When prospects say "let me think about it" and ghost afterward, the pain is not high enough in the sale. The response to "let me think about it" should be "Awesome, what's your main concern?" The question asked most frequently in these situations is "What are you most afraid of? What are you afraid of having happen?"
Two elements feed into the sales motion: qualification and education. Qualification means talking to the right people who meet BANT criteria: budget, authority, need, and timing. If the correct avatars meet BANT criteria, then it is an education issue requiring more friction prior to the conversation.
Sales at the micro level locally increases the value of an outcome. The goal is to elevate the relative importance of one thing in prospects' lives more than others. This involves both carrots (how much better life will be with this thing) and sticks (how shitty life will be without it). Future pacing pain means asking what life will look like a year from now if nothing changes.
When someone says they need to think about it, the response should not be to back away from the sale. Instead, assert that decisions take information, not time, and position yourself as the source of information. Asking "What's your main concern?" serves as a triage question that gets back into the conversation.
When someone says they are busy after being asked on a date, asserting dominance by questioning whether they are really busy shows confidence. Prospects want to feel that the salesperson is confident and certain. Backing away from the sale too easily causes prospects to leave.
A listener overheard a sales conversation at a bar where a seller offered 10 tons of 6061 aluminum at $400 per ton, negotiated down to $385 per ton for immediate pickup with one-page paperwork and cash on delivery, sealed with a handshake. This exchange represents traditional commodity sales where the only variable negotiated was price, with the seller emphasizing 30 years of business experience in the same manner.
Commodity sales operate on a race to the bottom because margins are thin and differentiation is difficult. The speaker prefers selling intangibles around commoditized products, such as speed of delivery, risk reversal, service quality, and brand value. Without these elements, sellers remain stuck with commodity margins that are not sustainable.
A listener raised prices by 40% after three years of undercharging, lost 30% of clients, saw revenue increase, but questions whether the increase was too steep. When the speaker tripled gym membership prices from $99 to $299 monthly while transitioning from large group boot camps to semi-private training (one-on-six or one-on-eight), they also lost 30% of customers but doubled revenue while reducing delivery costs by one-third.
The point of maximum profit is not the point of maximum yeses. Only one entity in any market can be the low-cost leader. If pursuing that strategy, the entire business must be designed around minimizing costs from day one, similar to Walmart's approach. For service businesses in developed countries, being the low-cost leader requires AI implementation and offshoring to maintain margins.
When prospects compare pricing to competitors, use the cheap comparison close: Ask which option they would choose if prices were identical. When they select your offering, ask why, allowing them to articulate the value differences. Respond with "That's why we're more" delivered with light laughter rather than stone-cold seriousness to maintain rapport.
Selling low-priced items requires minimal sales skill because price itself becomes the justification. Higher-priced offerings demand actual sales aptitude to articulate value without the crutch of being the cheapest option.
The number one leadership tip is defining what good looks like. Without clear definition of expectations in terms of desired outcomes and the methods to achieve them, feedback cannot be given, coaching cannot occur, and standards cannot be upheld. People cannot model behaviors they cannot identify.
Communication requires describing desired outcomes in observable, measurable terms that can be seen with eyes or performed with hands. Instead of requesting someone "stop being lazy," specify "respond to Slack messages faster." Observable metrics eliminate misinterpretation and create concrete understanding between parties.
The couple sacrificed health, vitality, friends, time, living preferences, fun, drinking, and socializing to focus exclusively on work. They lived in locations they disliked because moving would consume time better spent working. They avoided activities common in Austin such as LSD experimentation. The disproportionate outcomes resulted from disproportionate input over an extended period, made more tolerable by doing it together.
The couple explicitly states this approach is not recommended for everyone and that outcomes may not replicate for those following identical paths. Uncertainty exists about whether different choices would have produced different results.
A developer built a successful skincare product for climbers that received positive brand and messaging feedback but struggles with sales. Brand appreciation does not translate to purchases. The measurement of brand resonance is whether people feel compelled to buy.
Finding customers represents the primary challenge in a niche-of-a-niche market. Two approaches exist: locate the small subset of climbers already dissatisfied with current skincare options, or create problem awareness among climbers and outdoor sports enthusiasts who may not recognize their skincare issues.
When selling products, focus on articulating problems customers experience rather than listing ingredients or technical specifications. For climber skincare, mention issues like product getting in eyes or affecting grip, then state the product solves these problems specifically for climbers. Low-stake purchases increase likelihood of trial when problems are clearly articulated.
Start with climber influencers for product placement and promotion, then move to direct-to-consumer sales and advertising. Products that succeed in extreme niches can expand outward because customers assume if it works for demanding conditions, it will work for their less extreme needs. Patagonia exemplifies this progression from hardcore outdoor users to mainstream adoption.
Good writing ensures someone understands the content. Good copy makes people feel understood.
When prospects respond that they're busy, the core issue is that the salesperson is not giving them a reason to listen. The ask is too high relative to the benefit being offered. Cost is measured by how much time prospects believe they'll need to give, while benefit is the reason being presented. To improve outcomes, strengthen the reason and reduce the ask.
Asking for 15 minutes is typically too much; instead, request 60-120 seconds to get a foot in the door. Once engaged, the conversation can expand naturally. Oz the mentalist used this approach during street performing by asking "30 seconds?" and promising the most amazing trick in the world. The low time commitment made prospects agree, after which he would retain them for 10 minutes.
A medical practice experiencing 13 no-shows per month, representing 25% of slots, needs to implement a deposit system despite owner concerns about appearing rude in a small town. A deposit is standard practice, comparable to hotel reservations, especially when provider time has significant value.
Four levels of friction can be implemented:
- Lightest approach: No card required, but use an integrity tie-down after confirming the appointment time by asking if they are a person of integrity who keeps commitments, then explaining that no-shows cost real money
- Next level: Request a card on file with a stated $200 no-show fee for cancellations within 24 hours, framed as standard business practice to respect provider time
- Higher friction: Charge for the consultation upfront and apply it to any future services purchased
- Maximum friction: Charge for the consultation independently of whether the patient proceeds with treatment
Losing 25% of slots directly impacts revenue. At 10% margins, capturing that lost capacity could result in a 3.5X profit increase, making it highly unlikely that implementing deposits would reduce overall earnings.
When two high-performing salespeople cannot work together effectively, address the issue directly by bringing both into a room for structured conflict resolution. The process involves:
- Having each person describe what happened and how it felt
- Asking each to identify something positive about the other person
- Having each person acknowledge what might be true about the other's perspective
- Practicing active listening where each repeats back what they heard and commits to specific actions to address the situation
- Requiring each person to make one concession or compromise
If the conflict persists and requires additional intervention, both individuals should understand that continued mediation will not be provided and their positions may be at risk.
Being perceived as aggressive during sales conversations typically stems from talking too much rather than listening. People believe almost nothing about what salespeople say and nearly everything about what they themselves say. The goal is to ask questions that allow prospects to reach conclusions themselves, since questions cannot be disagreed with in the same way statements can.
Statements should be minimized during sales conversations. When statements are made, they should either compliment the prospect on an inference or decision, or address purely logistical matters. The pitch itself should typically consist of a statement followed by an analogy rather than detailed feature descriptions.
No one cares about the full scope of what a business does. Prospects care about their own problems and whether solutions exist. Detailed descriptions of processes either sound like work the provider will handle (which prospects don't care about) or work the prospect must do (which they want to avoid). Analogies bridge this gap more effectively than comprehensive explanations.
For sales agencies working on contingency where clients pay only upon closing, a 10% fee charged to the client for a $2,000 course ($200 per sale) with 50/50 split between agency and salesperson requires evaluation based on supply and demand dynamics.
Compensation must reflect the skill level required to attract capable salespeople. More skilled professionals may require higher percentages due to the activity volume needed to generate results. Customer pricing follows similar principles: established businesses with strong demand can charge more, while those seeking business may need to adjust rates downward initially.
Service-based business pricing should increase over time as providers accumulate reviews, case studies, and word-of-mouth referrals, shifting supply and demand in their favor. Price serves as a strong quality signal for service providers.
For outsourced sales arrangements, agencies typically take 20% rather than 10%. A 50/50 split with the salesperson makes sense only when additional compensation structures exist beyond per-sale payments, such as continuity payments or activation fees. Total cost of sales for in-house teams should target 12% or less, including management, software, and compensation.
When team member performance declines due to personal circumstances, the amount of slack extended depends on their prior track record and goodwill accumulated. Long-term high performers (3-4 years) who have demonstrated consistent results deserve significant empathy and grace during difficult periods, with the expectation they will recover.
However, extended accommodation becomes problematic when declining performance compounds into additional issues like tardiness, disengagement, or unreliability that affects team dynamics. At this point, leaders must have direct conversations about expectations and timelines for improvement.
The distinction lies in whether someone is experiencing a temporary setback with eventual recovery, or whether they are developing a new negative pattern. Some individuals spiral from one difficulty into broader life disruptions including job loss, relationship problems, and health decline. Leaders must assess whether the situation represents a blip or the beginning of a sustained trajectory that will continue harming the business.
Documentation of accommodations made for struggling employees protects the organization by demonstrating reasonable efforts were made before taking more serious action, while also signaling to remaining team members that the work environment provides appropriate support.
When acquiring a franchise location where the previous owner had been collecting customer payments without fulfilling orders and voiding invoices to conceal the activity, resulting in approximately 60 businesses filing lawsuits, the location's reputation may be permanently damaged.
This situation illustrates why due diligence is a critical step in mergers and acquisitions processes. Such fraudulent behavior tends to occur during one-time transactions with high stakes and irreversible consequences, which precisely describes business acquisitions. The pattern has been observed multiple times across different transactions.
Acquisitions of businesses or real estate create huge incentives for short-term players to act unethically. The amount of money that can be made from short-term thinking can sometimes be enough to set someone up for life. When dealing with fraud or being taken advantage of, the bad news is that even if you sue, you only get money back if that person has the money, and the amount divided by other people suing them is enough to make you whole, which is unlikely. Suing takes a minimum of 2 years and requires sustaining legal fees. The recommendation is to take your licks, learn from the lesson, and commit to being bigger so the loss becomes inconsequential in the future.
The legal system is not a justice system. You will not get justice.
Companies often pay money in settlements because it costs less than fighting, and the strategy for those with resources is to out-sue others by making legal fees more expensive for the opposing party.
A sales manager is dealing with a VP who is sleeping with a new junior sales rep who has generated zero qualified meetings or sales in 5 months. The VP defends keeping her despite lack of experience and communication issues, citing the economy and a culture of "cultivating" talent. The manager witnessed them in a hotel bar and overheard the VP bought tickets to an industry conference in Dubai for prospecting.
There are four potential approaches when facing this type of workplace conflict:
- Go to the superior of the VP or HR to report the situation, which creates an enemy of the VP
- Ignore the ineffective rep and continue working to advance within the company
- Leave the company for a better culture
- DM the CEO or owner directly, requesting anonymity, to explain that the VP is blocking firing decisions due to a personal relationship, creating an authority-responsibility mismatch where the manager has responsibility for numbers but lacks authority to make personnel decisions
HR investigations would require pulling in the VP and conducting formal sexual harassment investigations.
The strategy for increasing sales while maintaining anonymity involves building a lifestyle personal brand that shows your face while hiding the actual product behind a paywall. The principle is that once customers have access to the product ("the milk"), they no longer need the source ("the cow"). Creating a branded experience around the content allows for marketing without revealing identity.
Customers use in-store sizing services then purchase the same items online at lower prices. Some admit this upfront while others attempt to hide their intentions. The fundamental issue is that if customers can buy identical products elsewhere, the store functions as a commodity middleman.
The recommended approach is to emphasize manufacturing variance even within the same brand and size - a size 10 shoe from the same manufacturer may fit differently across batches. Position the in-store selection as a "one of one" rather than "one of many," highlighting that online purchases may not match the exact fit achieved in person.
Small retailers face inventory challenges with carrying extensive size selections compared to online competitors with unlimited warehouse space. Some stores strategically avoid carrying certain sizes like XL to manage inventory.
Additional strategies include making shopping experiential and providing positive reinforcement during the fitting process to encourage impulse purchases, provided no direct charges are made for sizing services.
A salesperson who lost their wife of 10 years after 6 years in sales is experiencing panic attacks when attempting to make dials. The person who motivated their daily performance is gone, and they're considering leaving for a less stressful career.
It's unrealistic to expect immediate performance at pre-loss levels, especially right after returning from bereavement leave. Many people, particularly men, put pressure on themselves to prove they're the same person, but major loss changes you. Performance may actually improve after 1-2 years of processing the experience.
Steven Hayes developed acceptance commitment therapy after experiencing panic attacks. The key insight is that panic attacks are perpetuated by anticipating them and attaching negative meaning to the experience. The fear of having a panic attack becomes worse than the attack itself.
A practical technique involves confronting the fear directly - when someone was about to have a panic attack, the response was "Let's do it. Let's have the panic attack," which stopped the cycle by removing the fear of the emotion.
The cycle of anxiety occurs when people fear the emotion itself and attach meaning like "Now that my wife isn't here, I'm not going to be able to perform anymore." Backing away from dials allows the fear to win.
When experiencing major loss, changing feelings and thoughts is extremely difficult, but changing actions is possible. Even without believing it will work, acting as if you can overcome the situation allows the mind and emotions to eventually align with the actions.
Steven Hayes' perspective: if having a panic attack in front of colleagues, "that's their problem, not mine. I'll be fine, but they got to deal with whatever occurs in their head."
Three additional approaches for managing grief while maintaining performance:
- Distraction through work is valid - there's nothing wrong with not spending all time grieving, and no judgment should be placed on how someone processes loss
- Get back on the horse immediately to prevent misattribution of fear to the activity itself
- Reframe the motivation: instead of dialing for your wife who has passed, dial to make her proud, maintaining the same purpose with a different temporal relationship
The principle is that the deceased would likely want continued action rather than stopping, and distraction with meaningful work provides a healthy processing mechanism.
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