Business

I’ve Heard Hundreds of Pitches Running a 9-Figure Company — Here’s What Makes Me Say ‘Yes’

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Opinions expressed by Entrepreneur contributors are their own.

I’ve been in the hospitality industry for over 20 years, and it’s evolving today more quickly than ever. Like many CEOs, I am approached by vendors who are eager to show me the latest product or service they believe will revolutionize my business. And I get it — they are passionate about their solutions. Their teams pour time, energy and expertise into creating something they believe will change the game for restaurant brands. But here’s the truth that many of my peers and I agree on: not all pitches are created equal.

Over the years, I have chosen partners that align perfectly with my company’s goals, helping us grow and thrive in ways that benefit both parties. As more vendors come onto the scene, my teams have also been on the receiving end of pitches that were a waste of time for both us and the solution provider.

Time is one of our most valuable assets, and the right timing could also be the ultimate difference maker. Here are my tips to set yourself up for success and make your outreach count.

Table of Contents

1. Find the right person to pitch

Take the time to find the appropriate person at the organization to contact. It is most likely to get into the right hands if you do, and if they are interested, they can elevate it internally. If you’re marketing an AI solution, do some digging and find a tech leader. If it’s a marketing platform, find the CMO or the primary user of the platform.

CEOs are sometimes treated by a switchboard and asked to redirect vendors to the right person within our organization. It should go without saying that this method is unlikely to be effective. When I receive a real referral from a trusted contact at another organization who has vetted the product and seen value for their brand, I’m much more inclined to listen. Genuine referrals always beat cold outreach, and if your product is compelling, the genuine referral will come naturally.

2. Do your homework on our business

Many pitches we receive show the vendor knows nothing about our company. If you don’t understand our business model, challenges or where we are headed, how can you position your solution as the answer? There are common challenges in our industry, but that doesn’t mean there is a one-size-fits-all product that will address them. Personalize your pitching instead of a generic, scattershot activity that makes prospects feel like a number.

Vendors may be tempted to name-drop their biggest clients, but if you are trying to appeal to mid-sized or smaller companies, that can backfire. A better scenario would be a mutual connection reaching out to me on their behalf who thinks they could be a good fit, and recommending we connect.

Show relevant case studies that demonstrate how your solution has helped companies similar to mine. I want to see proof that you can help me succeed, not that you’ve landed Fortune 100 clients.

3. Get your company’s name out there beyond sales

Find ways to get in front of prospective customers, whether that’s media coverage, trade show presence, or other creative marketing tactics to build general awareness. Trade shows can be a goldmine for showcasing your expertise if you do it right. Attend sessions and use those nuggets to connect with other attendees or speakers. Refrain from aggressively pitching anyone who walks by your booth; instead, engage in a normal conversation to make a connection. That real connection you make can come back as a call to want to learn more.

One great recent example is a kiosk technology vendor that my company started working with last year. Our technology leader noticed the company at trade shows even before we were actively looking for a provider. We knew they worked with smart brands, similar to our size, we trust, not just industry giants. In our initial conversations, the company CEO and salespeople took the time to understand the nuances of our business and were clear about how they serve a range of company sizes. We found them to be a flexible provider that was super innovative and could bring great ideas to our business. They were honest that some of the capabilities we want are still in beta, and we could collaborate and grow together. That kind of transparency and flexibility is what builds trust and sets the stage for long-term partnerships. They continue to provide great support, and we have been learning together to make the kiosk experience for our operators and customers.

4. Be thoughtful with your outreach and avoid spammy tactics

Speaking of solutions providers, there are many ways to send mass emails. It’s not a bad thing to have email lists, but don’t overdo it on frequency, especially for cold outreach. Also, as more people use cell phones rather than office lines, your sales team should still respect their personal space and not text or call repeatedly, especially outside of traditional work hours. If you want to stand out, you have to be strategic and respectful in your outreach.

Think of it as an online dating site, and don’t pester people you are interested in. I have vendors who leave me two or three voicemails a week — all of which go unanswered. If your email or LinkedIn outreach looks like a generic copy-paste message, it will likely be ignored. Instead, focus on making real connections. Comment thoughtfully on posts that resonate with you. If you want to reach out, try a softer approach: “In case you ever need this, I’d be happy to share more.”

5. Set honest expectations and deliver on your promises

Nothing sours a business relationship faster than being sold by an A-team, only to be handed off to a less engaged support team after the contract is signed. Sometimes, even worse, the entire support function disappears, and we are left to implement and activate it by ourselves. This has happened with an industry-leading sales platform, and we were disappointed from day one and could not go fast enough through our contract terms. That company won’t be getting a happy customer referral from me. Sadly, I have been telling my peers to stay away. So, introduce your prospective client to the account management and client support team before they sign the dotted line.

Set realistic expectations and over-deliver. The result will be longer-term customers, and happy customers can lead to more introductions!

Pitch with purpose, not desperation

When times get tough and leads dry up, it’s tempting to resort to incessant cold calls and desperate outreach. But that approach can easily backfire. The best way to win your ideal customers is to pitch with purpose. In the end, winning the business doesn’t have to be the only goal. If both client and vendor can learn from the pitch process and gain valuable insight on ways to make improvements, that’s a big win.

Find the right person. Do your homework. Make genuine connections at trade shows. Be thoughtful in your outreach. Set honest expectations. And most importantly, build trust by demonstrating that you’re invested in mutual success.

Because at the end of the day, successful partnerships aren’t built on flashy pitches or aggressive tactics — they’re built on trust, value, and a genuine desire to help each other grow.

Intellectual Insider

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Business

Think In Two Timelines If You Want To Build Greater Wealth

If you want to grow your wealth faster than the average person, I suggest trying to think in two timelines that move together in unison.

The first timeline is analyzing what’s going on right now. The second timeline is analyzing what could happen in the future, with a consistent spread. It’s like having a dual computer processor always running in your brain.

I’ve been thinking in two timelines since 1999, when I got my first finance job out of college. Thinking this way was key to me building enough wealth to escape corporate America in 2012. I haven’t stopped thinking this way since.

Table of Contents

Example Of Thinking In Two Timelines For Greater Wealth

The classic example to explain my suggestion is to people who are currently working.

Timeline #1: How do you feel about your job now?
Timeline #2: How do you think you will feel in ten years if you are still doing your same job today?

Most people I talk to never think about question two when they first start their job. They are thrilled to be there and full of optimism. But I want you to think about question #2 because I’m trying to get you to forecast your misery.

If you can approximate when you’ll be miserable at your job, you can take steps to prepare for when that misery comes. But if you don’t think about question #2 consistently in two timelines, by the time you are miserable, you are screwed. You have little-to-no options for getting out of a suboptimal situation.

Saving And Investing Enough To Break Free From Misery

When I was told I had to get in at 5:30 a.m. and stay past 7 p.m. to ensure I got the appropriate research from my colleagues in Asia for clients, I knew I couldn’t last 40 years in a career like my parents did. Instead, I made a more realistic assessment: how long could I conceivably last before burning out completely? The answer I came up with was age 40.

So I calculated how much I would need by then to have the courage to walk away. That number was $3 million. Depending on how the net worth was structured, it could generate potentially $100,000 a year in passive income. From that moment on, saving and investing $3 million became my mission. I constantly visualized what life would look like at age 40, 41, 42, 43, 44, 45, and beyond—free from the grind with that money in mind.

This two-timeline approach—present-day hustle paired with future-day dreaming—kept me focused and motivated. I truly believed that if I didn’t hit that net worth target, I might short-circuit my life from all the stress and hours. I was already beginning to suffer from plantar fasciitis, uncontrollable allergies, and weight gain.

In the end, I left three months before my 35th birthday thanks to an unexpected variable: the ability to keep all my deferred compensation and receive a six-figure severance package after 11 years at my last firm. That severance covered five years of normal living expenses. With that financial cushion in hand, I knew it was now or never—so I took the leap of faith.

Using Two Timelines To Become A Better Investor

Now let’s apply my two-timeline approach to investing.

1) Present Timeline:

Investors have done incredibly well since 2020, especially those who bet on tech. With the S&P 500 up more than 20% in both 2023 and 2024, the investor class has built far more wealth than expected. Real estate has also performed strongly since 2020, although some markets—like Texas and Florida—are correcting. Every investor should look at what their net worth was in 2020 and celebrate.

Average household wealth by income bracket in America, top 1% versus middle class

2) Future Timeline (10–20 Years Ahead):

If you or your parents don’t invest aggressively, life could stay in hard mode indefinitely. The wealth gap has already widened dramatically since 2020, and it’s likely to keep widening. In 10 to 20 years, buying a primary residence might be next to impossible. Finding a job that pays a livable wage could also become increasingly difficult as AI disrupts more industries.

What should we do?

Average household assets breakdown by inc

The Plan To Ensure The Future Will Be OK

I’ve developed a general game plan to give my family a fighting chance to compete in an increasingly competitive and uncertain future.

1) Hold onto our primary residence and at least two rental properties to stay long real estate.

Real estate is one of the most reliable ways to build and preserve wealth over time. By holding onto property, we not only benefit from potential appreciation and rental income, but we also protect ourselves from being priced out of housing in the future. Owning one rental property for each child is something you should consider.

2) Build two 529 plans that equal the current four-year cost of the most expensive university today.

College tuition continues to rise faster than inflation, and there’s no sign of it slowing down. Fully funding 529 plans now ensures our kids will have the freedom to choose quality education without being burdened by debt—or burdening us. They will also have the option to attend the best college that accepts.

3) Invest at least the gift tax limit every year in each child’s custodial investment account and Roth IRAs.

By consistently contributing early, we harness the power of compounding. The goal is to build a financial foundation that allows them to pursue careers they enjoy, not just ones that pay the bills or seemed “high status” by society.

4) Aim to invest at least $100,000 a year in risk assets for the next 20 years for ourselves.

To combat inflation and maintain purchasing power, consistent investing in equities, venture capital, and other growth-oriented assets is critical. This aggressive approach is our hedge against stagnation and the rising cost of living. It won’t be easy as a writer, but I’ll somehow find a way through other activities.

5) Build $500,000 in private AI company exposure to hedge against a difficult job market in the future.

AI is both a threat and an opportunity. By investing in private AI companies or funds, we aim to participate in the upside of technological disruption, rather than simply becoming victims of it.

Why a $500,000 Investment in AI Makes Sense

Ever since 2017, I’ve been grappling with the reality of having to pay for college starting in 2036. Based on current projections, we’re looking at around $450,000 for public and $750,000 for private university tuition over four years. That’s a staggering amount—especially considering most of what’s taught in school today is freely available online.

One solution is to guide them toward attending community college for two years before transferring to an in-state university. Another is to educate them ourselves, or at least as much as we possibly can before they are adults.

But perhaps the most compelling solution is to invest in the very technology that’s likely to disrupt traditional education the most: artificial intelligence.

The Potential Returns On A $500,000 Investment

At first glance, allocating $500,000 to private AI investments may seem excessive. But when you compare that to the potential $450,000–$750,000 cost of college in 2036, it starts to look like a rational hedge.

The logic goes: if I’m willing to spend $450,000 to $750,000 on college in 2036 per kid, then I should absolutely be willing to invest $500,000 or more in the very companies that might make traditional education obsolete. Heck, I should be willing to invest $900,000 – $1.5 million in private AI companies now that I really think about it.

Here’s a breakdown of how a $500,000 investment grows over 10 and 20 years at different compound annual growth rates (CAGR):

Annual Return	10 Years	20 Years

A $500,000 investment compounding at 15% annually over 20 years grows to about $8.2 million. Can you imagine having the option to access that kind of capital in your mid-20s? While 15% is an aggressive target, these types of returns are far more plausible when investing in earlier-stage private companies.

Just look at the performance of early investors in OpenAI, Anduril, Scale AI, Databricks, and Anthropic—many have achieved well over 50% annual returns since their Series A rounds.

As a private equity investor since 2006, I’ve had a number of multi-baggers across various funds. The real challenge, however, is having a large enough position in these winners to materially move the needle. The other challenge is not investing in too many bagels (100% losers) that drag down the overall performance. Not easy.

Think in Two Timelines to Live Without Regret

The present is fleeting, and the future is always approaching. To live richly, we must learn to hold both timelines in mind: who we are now and who we hope to become.

It’s not enough to simply dream of a better future—we must consistently act in alignment with that vision. Otherwise, we risk drifting through life, only to one day wonder where all the time went.

We will all grow old. And when that moment of reflection comes—when the noise quiets and the days are nearly spent—I hope we don’t look back with regret. Not for the risks we took or the failures we faced, but for the plans we never made and the steps we were too afraid to take.

Live today with tomorrow in mind. That’s how we give meaning to both.

Suggestions

If you’re looking to invest in private AI companies, check out Fundrise’s venture capital product. The minimum investment is $10 and you can view what Fundrise is holding first before making an investment decision. I’ve personally invested $153,000 so far and I will continue to dollar cost average in to build my AI position to $500,000.

To expedite your journey to financial freedom, join over 60,000 others and subscribe to the free Financial Samurai newsletter. If you want to get my posts via e-mail as soon as they come out, sign up here. Financial Samurai is among the largest independently-owned personal finance websites, established in 2009. Everything is written based on firsthand experience and expertise.

Intellectual Insider

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Business

How Building Gaming Tech Led Us to a Business Breakthrough

Opinions expressed by Entrepreneur contributors are their own.

Over the past decade at Improbable and now with Somnia, I have worked on solving some of the hardest problems in the new digital age. We’ve learned a great deal from powering massively multiplayer video games, immersive virtual events and defense simulations so sophisticated they got me sanctioned by Russia…

But in the process of building tools for virtual worlds, we discovered something far more foundational: The infrastructure we needed for the metaverse turned out to be exactly what businesses need to operate in the AI era.

Like many, we expected that the surge of interest in the “metaverse” in 2021 would be a tipping point. After all, we’d been working on persistent virtual spaces since 2012. But the deeper we got into the problem, the more we realized the infrastructure wasn’t ready. Virtual worlds that allowed thousands of people to move freely across different platforms with their identity and assets intact simply weren’t feasible with existing systems.

Blockchain, on paper, offered the right ingredients: user ownership, decentralized control and the ability for different developers to build on shared standards. However, when we tried to use it for real-time interaction, it collapsed under the weight. These systems were too slow, too expensive and entirely unsuited to applications that needed responsiveness.

Imagine trying to run a Zoom call where every frame of video had to be verified by thousands of computers before it could appear on screen. That’s what we were dealing with.

Eventually, we faced a choice. Either continue building applications on infrastructure that couldn’t support them — or build the infrastructure ourselves. What we ended up creating, Somnia, started as a necessity for gaming. But it has become a blueprint for how business will operate in a future shaped by artificial intelligence, digital identity and real-time interaction.

The new demands of digital business

Three trends are colliding to reshape how modern organizations operate. First, AI is no longer just a chatbot; it’s an actor. Agents powered by large language models are starting to participate in digital ecosystems. In our testing, we’ve seen AI agents generate thousands of transactions per second simply through their interactions with each other and with users.

Second, digital ownership is shifting from a niche crypto concern to a mainstream expectation. People increasingly want control over their digital identities, possessions and reputations — and they want these assets to persist and travel with them.

Third, businesses are shifting from transaction-focused to relationship-focused models, where continuous engagement in digital environments drives loyalty and growth.

The infrastructure to support this convergence didn’t exist. So we built a system that could process over one million transactions per second, about 20,000 times faster than traditional blockchain systems. To put this in business terms: Imagine the difference between a corner store that can serve 50 customers a day and a Walmart Supercenter that can serve 50,000.

Beyond gaming: Business applications and cultural impact

This leap in performance has implications that go far beyond gaming and drive real business outcomes. Retailers can track inventory changes across thousands of stores in real-time for a fraction of a penny per update. Manufacturers can build secure, verifiable supply chains that don’t compromise speed. Financial institutions can process compliance checks, document verification and settlements with both transparency and efficiency.

But the bigger shift is cultural. As AI begins to automate routine tasks, we are entering what I call the “Fulfilment Economy,” as mentioned in my book Virtual Society: The Metaverse and the New Frontiers of Human Experience. This is not just about productivity. It is about meaning. People are looking for purpose, community and creativity in the digital environments where they now spend increasing portions of their lives.

AI helps by saving time and taking on the burden of process, allowing us to focus our energy on more valuable activities. These environments go beyond entertainment. They are places of work, collaboration, identity and economic activity. In many cases, AI agents will participate alongside us.

For businesses, this presents a strategic shift. When your users don’t just consume your products but contribute to and build on your platform, your role changes. You’re no longer just a provider; you’re a host. Your brand becomes part of an ecosystem — one that thrives on participation, portability and interaction. Supporting this shift requires infrastructure that can scale in real time, preserve ownership across environments and connect disparate platforms into a single seamless experience.

What comes next

Most business leaders aren’t thinking about blockchains, consensus algorithms or transaction throughput — and they shouldn’t have to. What matters is whether your company is ready for a world where intelligent agents transact alongside humans, where users carry persistent digital identities between services and where engagement happens in real time, not just during scheduled interactions.

The hype cycle around the metaverse may have passed, but the vision of shared, persistent, intelligent digital environments is more relevant than ever. What started as a solution for virtual worlds is now becoming the foundation for how businesses will deliver value in an interconnected, AI-driven future.

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Intellectual Insider

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Business

This One Leadership Move Will Transform Your Team’s Loyalty and Performance

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Opinions expressed by Entrepreneur contributors are their own.

For years, leadership development has focused on hard skills like operations, finance and technical know-how. But today, there’s growing recognition that soft skills — especially emotional intelligence (EQ) — are just as vital, if not more so. EQ isn’t just about being “nice” or managing conflict — it’s about cultivating trust, improving communication and building resilient, high-performing teams.

In a fast-changing workplace where expectations are rising and retention is a top priority, EQ has become a business imperative.

Table of Contents

Self-awareness beats spreadsheets

Emotional intelligence starts with self-awareness. Leaders who understand their own emotions are better equipped to manage stress, give feedback and respond thoughtfully in challenging moments. And yet, many overestimate their emotional awareness. In a survey of more than 1,000 professionals, 20.6% of men and 17.1% of women believed they were more emotionally intelligent than their behavior suggested. That gap matters because blind spots in leadership often become pressure points across an organization.

Building EQ involves engaging both verbal and nonverbal communication skills. This means not only listening and adapting but also reading emotional cues, responding empathetically, and modeling openness. It’s less about control and more about connection.

Don’t just know it — practice it

It’s not enough to understand EQ in theory. Like any business skill, it takes action to develop.

Leaders can strengthen their emotional intelligence by:

Participating in coaching or mentoring programs
Joining leadership development cohorts that include peer feedback
Having real, honest conversations with employees about emotional wellbeing

The most effective organizations embed EQ into their culture, starting with hiring. When emotional intelligence becomes a hiring lens, companies reduce mis-hires and build more cohesive teams. Ask candidates how they navigate disagreements, respond to constructive feedback, or bounce back from failure. Their answers reveal more than technical skills ever could.

Emotional intelligence isn’t optional at the top

Leadership isn’t just about setting strategy — it’s about setting the tone. Executives who lack EQ often struggle to inspire trust or connect across teams. They may deliver results in the short term but fail to build sustainable momentum.

In contrast, emotionally intelligent leaders:

Attract and retain top talent
Understand team dynamics and resolve conflicts early
Foster a culture of psychological safety and high performance

These leaders also lead by example. When executives participate in team trainings or feedback sessions, it sends a powerful message: growth is for everyone, not just junior staff.

Empathy is the new currency of culture

Today’s workforce expects more from leadership: more empathy, more flexibility and more humanity. They don’t just want a job — they want to feel seen, valued and supported.

When companies prioritize EQ, employees respond with higher engagement, better communication and deeper loyalty. That’s not just good for morale — it’s good for business.

The result? A workplace where people thrive, performance improves and culture becomes a competitive advantage.

EQ is the edge

Emotional intelligence isn’t a bonus trait — it’s a leadership essential. Developing it takes intention, but the return on investment is exponential. Stronger teams. Smarter hiring. Greater retention. Better results.

When EQ becomes the standard rather than the exception, everybody wins.

In a fast-changing workplace where expectations are rising and retention is a top priority, EQ has become a business imperative.