🌼10 Lessons I Wish I’d Learned Before 10+ Years of Entrepreneurship


🌼10 Lessons I Wish I’d Learned Before 10+ Years of Entrepreneurship

## They have cost me hundreds of thousands to learn, but will increase your productivity, profitability, and rate of success

When I [quit my 6-figure Wall Street job](https://index.medium.com/how-to-get-and-leave-a-6-figure-job-in-your-early-20s-from-an-ex-wall-street-banker-turned-ceo-c72e6f62f3ea) to embark on my entrepreneurial journey, I should have been primed for success. I had the finance background, business degree from a top university, and I’d already helped co-found a successful startup that ended up exiting (without me) a few years after my departure. Plus, I’d been an avid reader of all things “startup”, as well as a loyal Shark Tank enthusiast, which should count for something, right? _Not exactly._


Read also: 12 sentences about success no one wants to hear

Unfortunately, the one constant in entrepreneurship is the inevitability that most founders learn their biggest lessons through firsthand mistakes, and no amount of preparation nor credentials can fully [shield us from those painful experiences](https://entrepreneurshandbook.co/9-confessions-from-a-failed-startup-ceo-1eba03df071f). Nonetheless, I’m going to attempt to shield you from ten of them by sharing what I’ve learned over the past decade and hopefully make your entrepreneurial journey a tad smoother than mine.

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# 1. Faceless is better than the wrong face


Nowadays, with the rise of social media and the “influencerpreneur”, many aspiring entrepreneurs believe that in order to build or grow a successful company, they need to be the face of the entity. As someone who’s built multiple companies for which [I’m nearly anonymous](https://entrepreneurshandbook.co/a-fascinating-behind-the-scenes-look-at-building-a-new-atypical-business-b38c7925ff1c) (and have helped hundreds of entrepreneurs do the same), I can assure you being a client- or market-facing founder is not a requirement for sales or success. In fact, for many entrepreneurs, [doing so can be to their detriment](https://entrepreneurshandbook.co/just-because-it-worked-for-that-influencer-doesnt-mean-it-s-going-to-work-for-your-startup-7d760f799272).

If you’re a first-time founder, too young, too old, or in some other way not quite aligned with the type of persona your target market would most gravitate towards or respect, putting your face at the forefront of your company, sales, and marketing could be a grave mistake.

For example, I’ve worked alongside college student tech founders launching a marketplace app for which they needed to solicit paying B2B clients. The secret to their success is that they presented themselves as “interns”, rather than founders, and the mom and pop shops thus respected them, assuming their startup was much larger, more established, and run by a much more seasoned and mature CEO. In reality, these two 20-somethings were making all the magic happen, but presenting as such would have dashed their venture’s credibility in their prospects’ eyes.

Before deciding to be the face of your company, ask yourself if you really should be front-and-center as the founder, expert, CEO, and client-facing salesperson. The answer may be yes, but for green first-time founders who lack deep industry expertise or a specific connection to their prospects, it’s oftentimes “no”.

# 2. The sign to ditch your marketing or your product

There’s a saying in entrepreneurship that if you aren’t doing something that scares, challenges, or makes you uncomfortable every single day, you aren’t reaching your full potential. While I agree that we should all aim to stretch our capabilities and expand our expertise and skill set, there’s a difference between acquiring a new skill and going perpetually against the grain of our interests, preferences, and comfortabilities.

I once [hired a marketing team](https://entrepreneurshandbook.co/how-i-got-scammed-out-of-30-000-by-a-social-media-marketing-agency-568e7f2d2370) for a prior venture who was emphatic about the type of content we create. From the rebrand to the sales pages to the ads and video editing, I hated every single piece of it. [It felt icky](https://entrepreneurshandbook.co/how-i-got-scammed-out-of-30-000-by-a-social-media-marketing-agency-568e7f2d2370), made me insecure, and made me loathe the very business we were building. Nonetheless, I was willing to give them a chance because perhaps they were right; maybe I was just being stretched beyond my comfort zone.

Spoiler alert: If you can’t stand your marketing or your product for a day or a week, you definitely won’t be able to stick with it for the months or years required to see success. It didn’t matter if the issue was my limited comfort zone; if I couldn’t get on board with how we were marketing the product, it was never going to be successful in the long run.

If anything about your business gives you the “ick” on a recurring basis, that may not be a sign that you need to “challenge” yourself, but rather an indicator that you’re [headed down the wrong path](https://entrepreneurshandbook.co/an-8-figure-entrepreneur-whose-client-scammed-me-out-of-30k-sold-her-business-to-become-a-witch-45d7878b9325). There are many ways to build a successful business, and you can most certainly get there while maintaining your confidence, happiness, and integrity.

# 3. You don’t have to spend money if you have this

I’ve sunk 6+ figures (of my own life savings) into failed startups, and I’ve also turned less than $1k into $400k+ (that’s [the actual, ad-free 400x return](https://entrepreneurshandbook.co/the-formula-that-got-my-business-a-200x-roi-in-our-first-90-days-2b0d12fa5f91)), and I guarantee you there’s one major difference. With the 400x return startup, I single-handedly account for more than 90% of our sales with my own efforts, despite the fact that I do employ hired teams and technology for a few essential operational and in some cases revenue-generating tasks.

The difference, however, between the ventures on which I’ve spent the most money and reaped the least rewards and those I’ve spent the least money and reaped the most rewards is simply the exchange of time versus money. That said, it isn’t just time; it’s [time that’s been used to amass and improve skills](https://entrepreneurshandbook.co/the-quickest-way-to-spot-an-impending-decline-in-your-entrepreneurial-success-dbecb6cb57e).

If you have a large amount of capital (money to burn) and you’re short on free time or simply don’t like to learn, you can definitely drain your life savings and pray that you pay your way to profitability. For those industrious, resourceful, bootstrapped entrepreneurs who are willing to roll up their sleeves and get their hands dirty, I implore you to tighten your wallets and open your fists to the hands-on learning money can’t buy.

I promise, as someone who’s launched businesses cheaply and very expensively, you can choose to either spend time or money, but if you spend time wisely, the ROI will be tenfold with the transferrable skills and experience you’ll acquire.

# 4. The three investments worth your money early on

Along those lines, outsourcing and delegating too much, too soon is one of the gravest mistakes I see financially fortunate entrepreneurs make. Ironically, it tends to be the scrappy, cash-strapped founders who get the best bang for their buck, since they don’t have that many bucks to throw around. If you’re going to spend money on something early on, let it be _1. classes, 2. software, tools, & technology, and 3. expert mentorship_ (specific to your chosen industry or venture), rather than marketers or operators.

# 5. The key to inbound opportunities

For the first six or seven years of my entrepreneurial journey, I tried to hide behind a keyboard and my faceless ventures, keeping my digital presence to a minimum. To be honest, I’m still a fairly private person with a very limited online presence. Nonetheless, I did at some point become a bit more vocal, accepting a few interviews, sharing a bit of my journey, and offering outbound advice and anecdotes from my years of experience. Even with my limited public presence, I’ve noticed a marked shift over the past few years in which significantly more organic inbound opportunities come my way.

To name a few, I’ve been offered:

– Investment opportunities

– Advisor positions

– CEO roles

– Writing, consulting, speaking gigs, “entrepreneur-in-residence” jobs, and many more

Suffice it to say, once you develop a material level of expertise and enough success to back it up, deliberately crafting a professional public presence (and being vocal on a regular basis) can open the floodgates to countless unexpected opportunities. I’ve barely scratched the surface and have seen this shift firsthand, but I have friends and peers who’ve strategically engineered entire private equity and consulting firms around the inbound opportunities their digital presence attracts.

If you want opportunities to flow your way, you may need to open up more than you’re used to, and when the time comes, it just may be worth it.

# 6. These are not worth it

As entrepreneurs — and first-timers especially — it’s easy to allow our enthusiasm and desperation for success to taint our objectivity around a prospect’s “fitness” for our product or service. Simply put, we sometimes care so deeply about nabbing those first few sales that we fail to contemplate what happens after the credit card is swiped if the customer is unhappy. Despite the thousands of happy customers and client testimonials my businesses have amassed, [the ones that stick in my mind](https://bettermarketing.pub/7-bizarre-customer-responses-that-will-throw-you-for-a-loop-9fb6b3595082) are the problematic few that couldn’t be pleased.

There is such thing as a wrong-fit prospect, and there are [insatiable people out there who will never be satisfied](https://entrepreneurshandbook.co/5-customer-horror-stories-that-can-make-you-regret-being-an-entrepreneur-3a760cc457e6), no matter how far above and beyond you go to please and placate them. Rather than spinning your wheels and your team’s time and resources trying to mollify cantankerous customers, it’s better to weed them out and cut your losses early on. These rotten apples can be far more damaging in the long-run to your company’s reputation, your other customers’ perception and experience, and your own confidence in the product or service you provide. They’re just not worth it; [I’d rather have no customers than bad customers](https://entrepreneurshandbook.co/im-making-an-unpopular-decision-my-customers-may-hate-d03609a0c1a4).

# 7. This is courageous and strategic, not cowardly and stupid

As you build your business, you may face challenges and setbacks that make you wonder if they’re really worth the uphill battle they present. The easy answer for driven, motivated entrepreneurs is to press forward, eager to conquer every obstacle in their path. While this may seem like the heroic or ambitious thing to do, it isn’t always the right choice.

At some points in your business, negative results may indicate that you should stop, regroup, or pivot, rather than keep trying to persevere your way forward. In my first solo-founded venture, [I had spent so much time and money (6+ figures and 18 months)](https://entrepreneurshandbook.co/my-startup-failed-and-its-all-my-fault-a35ee6265df9) building the product, that I felt like quitting would be cowardly, stupid, and deem my journey a waste.

Regardless, as I watched the [industry evolve, our competitors crumble](https://imrachelgreenberg.medium.com/how-much-is-an-influencers-following-really-worth-they-may-not-want-you-to-know-71391160f710), and my required marketing and tech budget balloon, deep down I knew the best course of action was to stop the action altogether. There was no use throwing good money after bad, and I didn’t need to fail farther to know we were headed down an ominous path towards a likely demise.

Point being, it’s braver to pull the plug once you realize failure is imminent, rather than to keep forging an uphill battle because you think you’re not supposed to quit. Sometimes quitting or pivoting is strategic, and it’s [better to book a loss and move on](https://entrepreneurshandbook.co/5-biggest-entrepreneurial-splurges-i-regret-and-5-i-would-do-100x-over-3c11284141c2) than to keep incurring greater losses for months or years to come.

# 8. You can’t keep this in a box

One of the biggest surprises I — and I’m sure many entrepreneurs — experienced is that once you decide to make your business(es) a top priority in your life, that decision will likely bleed into and test your relationships. You may need to prepare for a multitude of reactions from your friends, family, and partner, and while you shouldn’t necessarily let others discourage or disparage your mission, some of those voices may be worth listening to.

I’ve seen friendships, marriages, and families divided over one party’s entrepreneurial motives and their failure to properly communicate what they’re pursuing, why, and how this may affect those relationships. As much as I’m a proponent of building businesses, I’m also a firm believer that loyalty to your loved ones is of great importance. If you neglect to allow your partner, friend, or family a glimpse into what you’re building, don’t be surprised if they feel left out, disconnected, or resentful towards your abruptly altered priorities.

# 9. These won’t last, but they could destroy you

For any entrepreneurs out there wondering how it feels to hit a major milestone or financial high in business, I’ll tell you based on my experience: _Precarious._ [I could never enjoy the highs](https://medium.com/swlh/10-unexpected-things-that-will-go-wrong-once-your-business-takes-off-a7bca3b65ee1) — in fact, to this day I still can’t — since I’m perpetually afraid of the comparative lows that might follow. That said, every entrepreneur has a different relationship with their business’s success and growth.

Nonetheless, one commonality among us all is the fact that those highs may be fleeting, and we sabotage ourselves the moment we attach our confidence and self-worth to the financials of our ventures. If you do, the only guarantee is that your confidence and self-worth will ebb, flow, vacillate, and wane along with your business, and that emotional volatility can destroy and derail even the strongest of founders.

Read also: How to avoid financial procastination and Impulse buys

# 10. This is unfair, but true

I’m going to tell you something most marketers and entrepreneur “coaches” won’t: Business isn’t always fair. What I mean by that is that the very same actions will yield different results for different entrepreneurs, products, services, and companies, and a successful strategy can’t be seamlessly bottled or transferred. Sure, there are proven tactics and best practices, but applying them to your venture may not work nearly as well as it did for a friend’s startup.

So much of business, marketing, and growing your venture is trial, error, learning, and experimentation. There isn’t a “best way to market”; there’s a best way to market to your audience for your product or service, and even that may (probably will) change over time.

# The key to minimize costly lessons

Though you can’t eliminate mistakes, obstacles, and costly lessons from your entrepreneurial journey altogether, you can minimize them. How? By setting aside time on a regular basis to learn, grow, enhance your skill set, and expand the options in your toolkit. You may not be able to prevent a problem from occurring, but the more expertise and capabilities you have at your fingertips, the swifter you’ll be able to tackle said obstacle and creatively course-correct your way into your next big win.

Contributed by Rachel Greenberg

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