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Why hunger is necessary for innovation: How Parkinson’s Law hinders…

Over the years, I’ve worked with several large companies that have “intrapreneurship” programs, which refers to initiatives that allow employees at large companies to take on an entrepreneurial role within the organization. The main idea is that these ‘intrapreneurs’ will be self-motivated, proactive, and innovative, all the while remaining…
Jan 29, 202405 min read
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The pitfalls of mentorship and “Smart Money” in startups

A few weeks ago I wrapped up a structured incubator cohort where I mentored the founder of a food delivery app. Let’s refer to him as “Tim.”  Over a period of six months Tim eagerly took my advice as he and the team launched his startup. However, within a…
Jan 8, 202416 min read
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Driving disruption: Amazon’s expansion into car sales and what startups…

For decades, the auto sales sector, with its hidden fees, bait-and-switch financing, and pressured add-ons, has been stacked against buyers. The recent partnership of Amazon and Hyundai to sell cars online is about to change things.  With its patented one-click ordering, Amazon can now eliminate the need to endure…
Dec 12, 202305 min read
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3 Strategies in Surviving the 2024 AI Hype Cycle

We have all seen it countless times before: a hot new technology captures the tech world’s imagination and a handful of companies succeed in the gold rush. But thousands crash hard when the industry – overhyped by VCs, media, and starry-eyed founders – gets too excited about the space.…
Nov 28, 202305 min read
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SAFE for VCs, not so safe for startups

This year, the Silicon Valley-invented investment instrument, “Simple Agreement for Future Equity”, or the “SAFE” note, passed its 10 year anniversary.  This investment instrument has become extremely prevalent: by some estimates, it now outnumbers traditional stock offerings by a ratio of 2 to 1 for early-stage startups. SAFE notes…
Nov 20, 202314 min read
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Lessons from WeWork: When real estate pretends to be a…

Although I generally like to talk about how great disruption is in the innovation world, WeWork serves as a great lesson to founders that some business models are still very traditional and can be fatally undermined by flawed economics. In 2010, WeWork set out to “elevate the world’s consciousness”…
Nov 14, 202305 min read
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The scamming pandemic: How not to get screwed as a…

Falling victim to a scam is not uncommon for startups and their founders. Throughout my career I’ve seen all sorts of scams, from fake media outlet representatives whom you have to pay to publish an article about your startup, to unlicensed brokers who introduce you to investors for a…
Nov 7, 202306 min read
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Using this strategy, Steve Jobs and Jeff Bezos became tech…

A show called “Silicon Valley”, a brilliant parody of American startup culture, is much more true to life than most realize would believe. I’ve personally lived through many of the “fictional” scenarios presented in these comedy series.  In the show, one startup adopted a tactic known as “middle-out compression”…
Oct 31, 202304 min read
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News flash: Your startup’s investor pool just got way bigger

All startup founders know that getting investment is a difficult process, and it’s even harder for immigrant entrepreneurs. One of the reasons is the legal requirement that limits the pool of accredited investors who are allowed to invest in startups.  Until recently, only those with a net worth of…
Oct 17, 202304 min read
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Board of Directors vs Board of Advisors: Startup’s Brain vs…

Recently, I was working with a Latin American startup, let’s call them “TechNest” (not their real name), to develop a board of advisors. TechNest launched a smart home device and was considering expansion into the U.S.  The startup already had a board of directors, but a board of advisors…
Sep 12, 202305 min read
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The Peacock and the Octopus:How showmanship harms you and your…

The term “peacocking,” which is borrowed from the avian world, refers to when a peacock displays its vibrant feathers to impress or attract a mate or intimidate predators. The Octopus, on the other hand, tries to avoid attention, and many octopus species can camouflage themselves incredibly well, blending into…
Aug 29, 202314 min read
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The Arrow Information Paradox: How to sell without giving away…

In the startup world few concepts have been as intriguing as Arrow’s information paradox. Nobel laureate Kenneth Arrow posed these questions: How can you accurately price information without first revealing it? And once revealed, why would anyone pay for it? For startups in their nascent stages and vulnerable positions,…
Aug 22, 202305 min read
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Are startups overly dependent on Big Tech? A case for…

During my many years in the venture ecosystem I’ve never met a startup that did not rely on the capabilities of Big Tech for the core of its offering. This goes for AWS or Google Cloud powering back-end infrastructure; Facebook and Google Ads driving customer acquisition; GitHub facilitating software…
Aug 2, 202304 min read
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Why Uber is actually a law firm: How stealth business…

Do you think McDonald’s is a “fast food” restaurant? Well, they are not. Since 93% of all its locations are franchised, the company has a property portfolio worth $41.9 billion and generates almost all of its revenue from franchisees paying rent and licensing fees. McDonald’s is actually a real-estate…
Jul 18, 202306 min read
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Failing is good: Why a high failure rate is a…

Quite literally every accomplished founder that I know has failed at some point. Yet, the notion of failure sends a chill down most entrepreneur’s spine. It’s a taboo topic that’s rarely broached in the startup world. But could it be possible that we’re looking at this all wrong? Could…
Jul 11, 202306 min read
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Innovation in disguise: How “off-label” thinking fuels success

In the U.S., the Food and Drug Administration (FDA) approves medications for specific health issues. When a doctor prescribes a drug off-label, they’re recommending it for a condition or at a dosage that differs from the FDA’s approval.  This essentially means using an approved drug in an unapproved way.…
Jun 20, 202304 min read
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The second mouse gets the cheese: The myth of “first-mover…

I can’t tell you how many times I’ve asked an eager, excited, starry-eyed founder about who their freshly-minted startup competes with – and gleaming with pride many say “No one; we are the first.” On the flip side, when I ask a grizzled startup veteran they usually rattle off…
May 30, 202304 min read
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Do investors steal the ideas you pitch them? Yes, all…

A few weeks ago, I was speaking at a startup event. Afterwards, an immigrant founder approached me, asking for feedback on a new product for his early-stage startup. He asked me to sign a confidentiality agreement, as his idea wasn’t patented, and he was afraid that someone would steal…
May 15, 202305 min read
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Immigrant entrepreneurs created ChatGPT. Is AI a superior alternative to…

The popularity of ChatGPT by Open AI, founded in San Francisco in 2015 by a mostly immigrant team of Israeli-Canadian, Polish-American and other international backgrounds, has led to futurists spinning forecasts and theories about its impact on humanity.  Immigrant ChatGPT has become such a prevalent topic that recently UNESCO…
May 2, 202306 min read
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Is bootstrapping the most destructive American startup fantasy?

Throughout my startup journey, I’ve consistently heard experts praise the value of bootstrapping a startup. The startup landscape is saturated with countless inspirational quotes and headlines, such as “6 Quotes on business & personal finance from a bootstrapped-to-$100M-valuation founder,” from the now-rightfully-defunct Silicon Valley Bank’s “Wealth Insights” section.  This…
Apr 17, 202305 min read