8 Controversial Opinions That Can Catapult Your Entrepreneurial Success

Breaking these rules of business is your key to striking it big when everyone else opts for the status quo.

The other day, I was telling a family member a bit about a new business I’m working on. While it may seem like a surprising twist and an unexpected type of venture for me, it isn’t 100% out of my depth or all that different from other ventures I’ve successfully taken from zero to success pretty quickly. Nonetheless, this family member’s immediate reaction was “Why would you do that? You’re the completely wrong person for that business.”

He basically told me that while it may be a great idea with proven models of success and a cult-like audience of loyal buyers, it was outside my wheelhouse and I should stay in my own lane. He argued this point vehemently until I reminded him about a little experimental side hustle venture that was similarly outside my wheelhouse, yet in an industry I’d successfully infiltrated despite being the least likely founder.

The point here is simply that people will use common sense to put you in a box, tell you to stay in your own lane, and decide that there are certain things you can and can’t (or should and shouldn’t) pursue in business. As someone who’s successfully broken those rules and lived to profit handsomely and tell the tale, I reject those boxes, lanes, and wheelhouses, as well as those dictatorial voices expecting us to walk a straight entrepreneurial line. Here are 8 unpopular and controversial opinions that can make you significant upside if you dare to embrace them.

1. KYC is B.S.

Okay, so KYC (or “Know Your Customer”) isn’t necessarily worthless, but some people take it way too literally when considering which types of businesses they would or wouldn’t be equipped to build. For example, I’ve built and currently run multiple ventures for which I’m not the target market nor in some cases have ever been. Furthermore, I didn’t necessarily have access to or directly know a significant pool of people in the target market.

Nonetheless, I did know how to fill a gap and saw an opportunity to cater to these clearly defined markets with a product or service I could create or provide.

Many people — ranging from founders to advisors to investors — will argue that you have to actually be a member of your target market (or to have been one) to be able to successfully sell to them. This is where KYC gets a little out of hand and far more restrictive than need be.

Sometimes being on the periphery of your audience, yet knowing exactly how to create the type of value, product, or service they’re missing and craving, puts you in a unique position to serve said market. This is exactly why I have and continue to “infiltrate” industries and audiences where I might be least expected. Yeah, I’ve done the “stay in your lane” act with some success, but when I get bored and want a fulfilling challenge, changing lanes is an enjoyable climb, uphill or not.

2. It isn’t that serious

I am so beyond guilty of this — and I’m sure millions of other Type-AAA entrepreneurs are, too — but the truth is that you don’t actually have to take your business all that seriously to succeed. Let me clarify: Of course, you should approach a new venture with thoughtful strategy and ambition to push through the obstacles; however, sometimes we Type-A-ers especially put a little too much pressure on outcomes and tarnish the journey.

You know those people who seem to breeze through life getting “lucky” without a care in the world, trying things fearlessly and somehow reaching success that it seems one should have to suffer to achieve? They may not just be “lucky” or succeeding by accident…

I’ve found that some of my most successful ventures started out as fun side hustles and unlikely experiments that actually worked out or surprisingly blew up (in a good way). Sometimes putting too much pressure on a venture is what causes its demise and prevents you from being flexible enough to lean into what the market is asking of you.

More pressure doesn’t equal more money. More suffering doesn’t equal more success. More strategy doesn’t require less fun. If you find yourself in a financially-obsessed pressure cooker, cursing yourself for your venture’s shortcomings and slow progress, you may be pushing the pessimistic narrative upon your business.

There’s little more fun than making money from something you find fun, and many of us high-pressure, ultra-serious, success-obsessed founders could use a daily dose of that in our entrepreneurial pursuits.

3. Trends aren’t the answer, but they do hold the secret

When Covid hit, some people hopped on a trend and made a ridiculous profit off a current event (based on the pandemic-centric trends in consumer behavior). Many of those businesses were somewhat short-lived, leaving their founders shocked when the sales spikes died down or disappeared altogether. Others, however, were already plotting their next big thing — and it would be very much the opposite of what seemed “popular” or profitable.

This all comes down to having a contrarian mindset and, rather than relying on current trends, considering how you can use them to identify your future stealth, low-competition pursuits that will take the market by storm and surprise.

You see, if you follow trends and current events only, you’ll be both behind and fighting an uphill battle rife with crowded competition. If alternatively, you lean into the undercurrent of dissent (or the contrarian, less popular, or less mainstream viewpoint), you just may carve out a nice little niche of your own with a doggedly loyal following. This is a simple idea of “zigging” when everyone else is “zagging”, though so few of us actually do so.

4. If your venture requires you to go all-in 24/7, you’ve already lost

I’m sure you’ve heard and read from countless business and entrepreneurial thought leaders about how startup success means going all-in and working round-the-clock on one venture. While that may work for some, I can guarantee you it not only isn’t required, but it just may be setting you up for a venture you won’t love running.

After pouring more time than I’d care to admit into some failed ventures, as well as building some time-intensive successful ones, I decided to purposefully challenge the hustle culture mentality and attempt to build low-maintenance ventures. I’m not talking about companies that don’t require some time, effort, and perhaps capital, but rather I’m referring to structuring ventures that need little or less of your time as they grow.

One of the beautiful things about entrepreneurship is the ability to disconnect your income from your time, yet so few entrepreneurs actually optimize for this. So many are brainwashed into the idea that spending more time on a venture is a badge of honor that will surely pay off. In my opinion and experience, I’d rather build ventures that run and grow independently to free up more of my time to learn new skills, explore new industries, and probe new opportunities.

Between strategic planning, automation, and outsourcing, you can efficiently maximize the impact your venture has (and the income it makes) while minimizing the time, effort, and labor it requires.

5. No, you don’t have to put yourself out there

You may have heard the trope “investors don’t invest in ideas, they invest in people”; while that may be true for some investors, it doesn’t mean you have to put yourself out there front and center to succeed in business.

I’ve personally experienced — and know multiple very successful founders (who’ve achieved 7 and 8+ figure exits) who’ve also seen firsthand — that publicly presenting yourself as the wizard behind the curtain of your venture isn’t always the best move. Unless you’re seeking funding or going through a thorough due diligence process, you shouldn’t assume that connecting your face, name, and identity to your business is a requirement.

When deciding who you want to be the public-facing identity connected with your venture, ask yourself:

• Does my identity resonate with my customers (or the people I’m targeting)?
• Does my personal or professional background align with the industry, brand, or venture I’m building?
• Is there any benefit to putting myself out there in connection with this venture (or would a different name, face, or identity resonate better)?

Based on your answers to those questions, you can decide the degree to which you want to “out yourself” in connection with this business. There are many successful and in some cases mysterious brands for which the majority of customers can’t name the founder or CEO, and that’s rarely by accident. Yours could be one of them.

6. Sometimes you should stop trying (failure is a sign)

As entrepreneurs, it’s easy to assume the secret to success is to never quit. There’s even a saying “winners never quit and quitters never win”. I hate to burst that fabricated bubble, but it’s simply not true. Some winners do quit once they realize a market is telling them to take a different turn or wind down a venture altogether. Likewise, some quitters who choose to heed that market feedback and wind down failing ventures in favor of other more promising opportunities do win.

Point being, sometimes failure is a sign, and fighting it forever (by trying to make a failing venture work at all costs) may not be the ideal takeaway. If you really can’t get a venture to work and feel like you’re climbing up a spike-covered tree, maybe you should back away from the friction and assess if the market actually wants what you’re selling or if there are better opportunities you’ve overlooked. You only have to be right once, but it may take knowing when you were wrong to get to that one right move.

7. If this happens, you need an escape plan ASAP

Some people say you shouldn’t fall in love with your business, and it’s true that allowing emotions to overshadow logic is a recipe for disaster in business. That said, if you do find yourself falling out of love with your business (or especially out of “like” with it), you may want to plot your exit strategy now and chuck a few new irons into the fire.

There are few things harder and less fulfilling than operating, sustaining, and growing a business you no longer enjoy; trust me — I’ve done it. While it’s doable, it’s unlikely to realize your greatest entrepreneurial potential nor to be the rewarding journey a different venture may offer. Though stepping off your current treadmill may feel like the scariest, riskiest step yet, it just may be worth it.

8. You might work better rich and retired (hear me out)

This is easily one of my favorite myths to debunk because I’ve seen firsthand just how wrong people are when they believe “you need to be [desperate/poor/unhappy/under pressure, etc.] to create a successful venture.”

I’ve said it before and I’ll say it again: Not all entrepreneurs work best under pressure, and some of us actually do our best work when we have the time, peace, and resources to devote to creating a great value-adding venture, rather than desperately clawing for the fastest ROI around.

You don’t have to be desperate to be successful, and in fact, desperation can come back to kick you by rubbing off negatively on your customers, partners, or investors, as well as urging you to take shortcuts for a faster return. If you’re fortunate enough to create a scenario in which you work on your entrepreneurial ventures because you want to, not because you need to, you can actually do a better job at pouring your energy into them. This is exactly why you have serial entrepreneurs who could technically be retired if they wanted to (from a financial standpoint), yet they choose to go right back up to the batting cage and swing again at a new venture.

I don’t believe money or security makes people lazy, unambitious, or dumb. Instead, I believe money and security can give the right people — the ones who at their core should be our next wave of innovators — the freedom and space to embark on new challenges and give these ventures their all for the well-being of their customers, rather than just themselves.

The uncommon key

If you gathered anything from the above unpopular and controversial, yet tried and proven opinions and strategies, it’s the fact that sometimes choosing the uncommon route is the very reason you’ll succeed. You can read every startup playbook on the market, but the person who can strategically disrupt the status quo and turn industries on their head profitably will be the standout player to beat. If you want to be like everyone else — including the majority of startups who fail — then do what everyone else does. If you want to be in the minority that succeeds, you may need to make a few uncommon moves.