7 Things I’d Do If I Were A Brand-New Entrepreneur (Or Hadn’t Had My First “Win” Yet) | by Rachel Greenberg

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7 things I’d do if I were a brand-new entrepreneur (or hadn’t had my first “win” yet). Get unstuck and 10x your value, competence, direction, and success as a founder by following these 7 steps.
Photo by Priscilla Du Preez on Unsplash

Let’s be honest: Most first-time founders don’t recklessly quit their job, burn the ships, and pour their lifesavings into a half-baked idea steeped in poor planning and incompetence. From what I’ve seen — and I see and hear from thousands of these newbie founders — many arrive at their startup idea with a sound plan, thorough research, and the enthusiasm to take their ventures to the moon.

They still fail.

Well, some don’t flat-out fail; some quit. Others flail around, lost and demoralized, asking themselves why they — often among the smartest, most driven, high-achievers with corporate or educational success in their rearview — can’t seem to figure out this entrepreneurship thing.

As someone who’s been there, done that, and spent 6-figures of my life-savings and 18 months flailing, failing, and quitting after 24 years of prior successes, I get it.

The problem isn’t that you’re incompetent or unprepared for the job. Instead, it’s likely that you’ve neglected 7 of the most important steps that will markedly enhance your odds of success and make you a far more valuable founder. Before you spend another dime or another minute on your struggling venture, take the time to consider tackling these 7 steps to redirect your startup journey.

The biggest travesty in the education, entrepreneurial coaching, and career counseling world today is the fact that 99% of people are never asked this question. When it comes to business, we decide we want to be founders because we see a problem that needs to be solved, a gap in a market, or simply get enticed by the “be your own boss” and “work from anywhere” lifestyle. However, building a startup isn’t just your career; it’s your life.

Therefore, I believe the most important question anyone and everyone should ask themselves before embarking on this journey is: What do you want your life to look like?

That might sound fluffy, pie-in-the-sky, self-interested, or trivial, but it’s actually the most vital answer required to guide you to success.

Some people say you should build a business around something you love; personally, I don’t quite agree. Instead, I believe you should construct a business and career towards the life you desire.

  • Do you care where you live?
  • Do you want to wear a suit and speak on quarterly earnings calls?
  • Do you want to get anonymously rich on cash-flowing businesses that may provide meaningless products or services you don’t actually love?
  • Do you want to change the world or solve a major problem for the fulfillment, even if the money never follows?
  • What level of financial comfortability or success do you require?
  • Do you want to work 140 hours a week, 40, or 4?

Once you’re able to honestly, thoroughly answer those questions and concoct a clear picture of the life you want, building a business that will work towards that goal will be much less foggy. You’ll instantly rule out certain options, rule in others, and reassess why you do what you do.

The worst thing you can do is work 5, 10, or 15+ years towards building a business that may — or may not — succeed, only to realize you’ve created a life you never wanted. I wholeheartedly believe startup success requires a clear-minded founder with a long-term vision, and that starts with you, not just your business.

I can’t tell you how many times a failing, flailing, or first-time entrepreneur will pitch me the idea to dig themselves out of their plateau by building, buying, and spending more. Here are the ideas I’ve heard:

  • Build new products
  • Fundraise for an app
  • Create some new proprietary software

It almost seems like building something — anything — new and tech-enabled into their business is the “get out of stagnation free” card…except it isn’t free, and there’s no guarantee it will improve the business at all. In one of my earlier startups, I too, was guilty of turning to overbuilding as a crutch for the real issues dwarfing our growth and profits.

That said, you don’t have to buy, spend, or build to rejuvenate the well that is your startup strategy. Instead, I’d suggest you first browse. However, let me be clear: This isn’t light, frivolous browsing for the next shiny object to come your way; it’s quite the opposite.

I’d suggest going to sites like Flippa or BizBuySell and spending a good chunk of dedicated time each day poring through the relevant, complementary, appealing opportunities available. I’m talking businesses for sale, apps, websites, blogs, newsletters, SAAS, all of the above.

This is no cursory glance, either. When I say pore through them, I’m suggesting you analyze and dissect the most interesting and relevant opportunities you find. Thanks to marketplaces like Flippa and BizBuySell, you can gather significant information and even contact the founders or builders to find out more.

Make no mistake: I’m not suggesting that you take advantage of the information these sellers have made available to take them down. I’m suggesting you glean knowledge, inspiration, and possibly find your next expansion opportunity, partnership, or developer through your search.

  • You may find an app that would actually complement your business and significantly enhance the user experience (and profit potential).
  • You may find a new lead generation tool you could implement.
  • You may stumble upon an interesting venture you do want to buy, partner with, or in some way emulate or adopt, to bolster your business’s offerings and upside potential.

The point is simply that when you rely solely on your own brain and whatever phrases it thinks to Google search, you severely limit your options. Put bluntly, you don’t know what you don’t know, and sometimes it takes seeing what others have done or are pursuing to ignite the spark of inspiration needed to push you to that next level.

I’ve come close to buying dozens of businesses, blogs, software, and apps. I’ve connected with and hired developers of others, and in some cases, I’ve found inspiration to build new ones myself. I can say for certain, my well would have run dry long ago if I solely relied on my limited scope of ideas and knowledge to drive every new opportunity for my businesses. If your business is stagnating or declining while relying solely on your ideas and strategy, you just may be the bottleneck after all.

Even though I took a sales class in business school and worked in sell-side M&A (Mergers & Acquisitions), quite literally facilitating multi-hundred-million-dollar company sales on Wall Street, I never actually learned how to sell. Sure, I may have learned some textbook techniques, and I’ve made my fair share of pitch decks, financial models, and confidential investment memoranda, but that didn’t require me to punch above my weight and personally attempt to sell something face-to-face (or screen-to-screen).

It wasn’t until I was knee-deep (as in more than 6-figures deep) into my second solo-founded tech startup that I got up the nerve to put aside my pride, overcome my discomfort, and hammer home the cold outreach.

I sent hundreds of manual cold emails to celebrities and their managers, learning on-the-job how to talk to A-list Hollywood talent agencies from my 457 square foot lead paint-covered apartment, pretending it wasn’t just me.

While my subsequent startups haven’t required as much cold outreach and I’ve swapped out manual marketing for digital automation, developing those sales skills early on is something I believe every entrepreneur should do — and that includes punching above your weight.

As a pre-launch solopreneur with no connections, no sales experience, and buckets of sweat dripping down my sides as I negotiated contracts with top talent managers and lawyers, I didn’t feel qualified. I didn’t feel confident. I didn’t feel prepared. I did, however, improve.

If you haven’t yet gotten the opportunity to experience your first high-stakes sales attempt, punch above your weight, and sometimes face rejection or learn the art of persuasion and how to overcome it, I would suggest you seek out these opportunities now.

At the beginning, sales isn’t comfortable. Startups aren’t comfortable. If you’re doing something that makes you uncomfortable in the service of acquiring a new skill or attaining a new client, partner, or opportunity, you just may be doing something right.

One of the most common temptations I see from new startup founders — especially when they’re struggling — is the desire to connect with a community of early-stage and first-time founders who may be experiencing the same. I get it: Founding a company can be lonely, and far lonelier when you feel like you’re quietly failing in anonymity. Nonetheless, I actually don’t think seeking solace in fellow first-time founders is the best use of time or networking resources.

Sure, having a community of likeminded fellow founders with which to commiserate can be comforting, but oftentimes those struggling founders aren’t the ones best poised to help pull you out of your funk. Instead, your time may be more valuably spent connecting with founders and companies in your industry (relevant to your venture) who may become potential partners, customers, or affiliates.

At the least, you could learn a bit more about how your industry works and what it needs. At best, you could make significant headway in developing revenue-generating relationships and perhaps find your venture’s next (or first) client(s).

Most importantly, when you’re reaching out to forge those industry-relevant relationships, you want to lead with what you can do for them. Don’t ask for a favor, a sale, or to pick their brain. Don’t pitch them a service or solution. Offer to freely scratch their back and lead with a benefit and no expectation for reciprocity or compensation. The reciprocity, compensation, and referrals will be far more valuable when built on solid ground, which rarely starts with a sales pitch.

This may be one of my most unpopular or divisive startup-building opinions, but I’ve seen far too many founders taken down by narrowminded, common advice.

  • Common advice: Spend 150% of your time on one thing (one skill, one venture, one industry, etc.).
  • My advice: Build yourself a hedge against failure by bolstering your main thing with another skill, venture, industry or opportunity.

Yes, it is possible that if you toil away for 7 years on one venture perhaps you’ll find massive success and it will all pay off. However, I can assure you there are many — I dare say far more — founders who poured countless hours and years into one thing that didn’t pan out, all because they believed a singular focus was “the only way”. In my opinion, a 150% singular, myopic focus on just one thing isn’t the only way; in fact, I think it’s the least strategic, least responsible way to set yourself up for success.

I’ve simultaneously built and launched three startups multiple times in my life, and that’s the only reason I was able to move on from failure as fast as I did. After spending my first 18 months of entrepreneurial life heads-down on a venture that did fail, I vowed to move my eggs into a few different baskets from then on out, and it’s one of the best decisions I’ve made.

  • You can learn a synergistic skill
  • You can get a degree or certification that will open up more doors
  • You can build businesses, services, or software that will scratch your own itch now that you’re a business owner and know what that itch is

No matter what business you’re founding, if you have even 5% to 10% doubts that it’s what you should be spending 150% of your time on, I’d suggest you be strategic and carve out time to learn and hone that second (or third, etc.) trick. You don’t have to be a one trick pony to grow into a unicorn, and you just may accidentally discover your greatest startup opportunities through those second and third tricks. From firsthand experience, I’ve had that happen more than a couple times.

As an entrepreneur, you may believe you’re only as good as your revenue or profit; personally, I believe you’re only as good as the knowledge, skills, and perspective you’ve accumulated. Revenue and profits can come and go with seasonality, market shifts, and competitive disruption. It’s the knowledge, skills, and perspective you — the founder — have amassed that will enable you to weather those downturns and come out positively on the other side, be that in a pivot or a whole new venture.

Therefore, I’d suggest you take a brutally honest audit of your mindless, tedious down time and time spent consuming fluffy, irrelevant, low-value content. Maybe it’s the gym listening to music, instead of a podcast, or perhaps it’s Netflix or even social media scrolling that’s stealing your time.

Regardless of what the cause, once you do that audit, I’d urge you to restructure your content consumption opportunities to allot at least 75% of that mindless, tedious downtime to consuming something substantive and educational. It can be motivational, but I’d steer you away from the fluff and towards the concrete, nonfictional, educational accounts from founders that have gone before you.

Personally, I listen to a podcast every time I’m walking or working out, and whether it’s a founder interview, SEO strategy deep-dive, or new content marketing outlook, I find I gain hours of effortless learning every single day. Why hours? Not only do I listen to these podcasts every time I walk, walk my dogs, or work out, but I listen at 1.5x to 2x speed (depending on the speaker), thus training my brain to consume information much more efficiently.

Some aspects of starting a business can be repetitive, boring, and to be honest, not the most intellectually stimulating or challenging — and that isn’t great for your intellectual market value. Once you start treating your brain like a muscle to be exercised and pumped up with knowledge and new challenges, you might find that the ideas, strategies, and perspective you bring to your startup significantly increase and improve, as well.

Speaking of working out, and as irrelevant as it may seem to your venture, I’d be remiss to leave this one out. Many founders — myself included in my first few ventures — end up losing themselves in the entrepreneurial struggle, putting all of their time into their startup and little to none into their own wellbeing.

Here’s the problem: If you, the founder, aren’t in your best physical and mental shape, you likely won’t be bringing your best to the table with respect to your venture.

Moreover, the longer and farther you let yourself go and push self-care and physical (and mental) health out of the picture, the harder it will be to get back to the you you want to be. A couple years into my founder journey, I found myself depressed, insecure, demoralized, and uncomfortable in my own body. I wanted to hide in my failure, but the more I isolated myself, the more I became ashamed of the person I was becoming.

I didn’t want people to see me failing. I didn’t want them to see me depressed. I didn’t want them to see me 20 pounds heavier than when I started out. Ironically, I was far too focused on how other people would see me and not at all focused on how I saw myself.

In truth, I was ashamed at how far I’d let my failure derail my identity and seep into other aspects of my life, including my health, confidence, and relationships. It took ripping the band-aid off, drastically shaking things up, and becoming the type of person and founder I’d respect and admire to course correct my journey. Nonetheless, delaying would have only made things worse and dug a deeper hole to one day crawl out of.

You don’t have to be successful at your first venture right out of the gate; few of us are. You do, however, owe it to yourself to be the type of person and founder you’d admire and respect. Don’t let one microscopic failure poison the other areas of your life; you’re more than your startup, whether it fails or succeeds.


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