7 Things I’d Do Differently if I Started My Business All Over Again

7 Things I’d Do Differently if I Started My Business All Over Again

That would have spared me tons of wasted time, lost money, and entrepreneurial insecurity.

7 Things I’d Do Differently if I Started My Business All Over Again
Photo by Christian Velitchkov on Unsplash

Most entrepreneurial journeys begin with a fair share of blunders — and mine’s no exception. While I’ve exposed my 6-figure failures and the tech mistakes that nearly set me into legal (and financial) hot waters, those major flubs are among the more obvious shortcomings that riddled my earlier startup career. There are, however, some more subtle, yet equally detrimental regrets that have plagued my businesses for years to follow and delayed or hindered my eventual successes.

Here are 7 things I’d do entirely differently if I started over my entrepreneurial career from day one — and sometimes, I wish I could turn back the clock and do just that.

The year before I started my entrepreneurial journey, I was making 6-figures on Wall Street, and my bank even paid for my meals. Unfortunately, I didn’t realize bringing my nightly sushi habit into the startup world was a costly and unwise decision.

As entrepreneurs, it’s easy to separate our personal spending from our business. However, if you’re funding that business out of your personal life savings, you might want to take an extra sweep through that grocery basket before swiping your card.

You probably won’t realize how the small daily decisions add up until long after they do, and I certainly succumbed to this financial foible. If I could go back, I’d head over to Amazon, Target, or the 99 Cent Store and stock up on a few months’ worth of canned refried beans. Refried black beans with a spritz of avocado oil and a sprinkle of salt will fool your taste buds into attributing Michelin stars to your dollar-store “cheffery”, and for just $1.99 per can, you really can’t go wrong.

Oh, and in case it wasn’t obvious, I’d extend the canned beans mentality to every personal financial decision I make. Unless a decision is making me money, it’s probably costing me money, and at the early stages of my startup career, I didn’t have much to spare.

Speaking of money, it’s the one thing I don’t want to be overly worried about amidst the financially trying journey of starting a new business. When I started my first business, I spent about 18 months spending money — without any coming in. Depleting my savings month after month wasn’t just scary; it was dumb. The best thing for my financial, emotional, and mental health would have been a part-time remote gig. Yes, I’m suggesting you take on a side job, even during the earliest stages of building your business.

Why? Cash flow. It’s the one thing you won’t necessarily have right away, and lacking it is the one distraction that can lead you to cut corners, take shortcuts, and inadvertently sabotage your burgeoning business in the process. If I could go back, I’d pick up a side gig to ensure I had enough cash coming in to consistently cover my basic personal expenses and bolster my security so financial distractions aren’t derailing my business decisions.

Want to know when — and why — I learned how to build my own websites? It was only after — and because — I’d spent over 6-figures delegating to developers and outsourced teams to build products I ultimately didn’t understand.

Want to know when I learned how to create my own automated sales funnel? It was after I realized I was incapable of tweaking the proprietary funnel for which I’d paid 5-figures.

In other words, being flush with cash was my biggest entrepreneurial curse in disguise. Unbeknownst to the newbie founder I was, I’d handicapped my own value-add, rendering myself pretty useless, thanks to an overreliance on delegation and paying my problems away. I thought money was the antidote to incompetence; in reality, learning is.

If I could go back to the beginning of my startup journey, I’d give myself a mandatory technology, marketing, and automation crash-course, ensuring I was comfortable with everything my business would or might employ. From building websites to writing copy, SEO, constructing sales funnels, automation, checkout pages, even video editing, I’d prioritize learning — and mastering — it all. ASAP. If you’re in the first few months or year of your business and you aren’t learning at least one new skill per week, you might want to reassess exactly how you’re spending your time.

The idea of starting a business might sound intriguing or glamorous, but for many entrepreneurs, there’s an inherent stigma associated with exiting the traditional path for a less certain one. Thus, it’s not unusual for founders to recoil into a bedroom, basement, or converted garage and whittle away at their nascent venture in isolation. Aside from my “roommate” (fiancé), I did just the same.

Not only did I distance myself from friends, family, and former peers and colleagues, but I also failed to expand my circle with new connections. While that temporary isolation may seem harmless and inconsequential, it’s anything but. Instead, working alone without an entrepreneurial network can significantly limit and delay future opportunities for success, simply because you don’t have any industry-relevant connections or support system.

In contrast, I know of multiple entrepreneurs who prioritized genuine, industry-relevant network-building at the forefront of their entrepreneurial journeys. I watched this pay off in 6-figure first-time launches, global collaborations and referral networks, and 7- and 8-figure joint empires that grew like wildfire. If I could go back, I’d start building my circle, establishing my foothold, and cementing future partnerships long before any of my “successes”. If you wait until you’re successful to start networking, you’re creating your own glass ceiling and delaying your ability to break through it.

Once you start a business, there’s a major downside few entrepreneurs anticipate: Everything you do, say, or post may now be associated with that venture.

That might sound obvious or negligible in its impact on your life, but in my — and many of my peers’ — experience, it can actually be incredibly stifling and suffocating.

Simply put, if my public presence is an extension of my business, I have to be on my best behavior at all times, which may also mean a limited level of transparency and a shrunken circle of opportunities to explore.

  • I can’t voice my business struggles, since this could spook customers or hurt my company’s reputation
  • I can’t share viewpoints, beliefs, or personal perspectives my company’s audience may not align with
  • I can’t publicly attempt experimental ventures, industries, platforms, or personal projects of which my business’s customers might not approve

In order to protect my public-facing, thriving primary businesses, I have to limit or curtail my foray into other opportunities, and that’s an incredibly suffocating sacrifice.

In retrospect, I’d love to go back and create two separate profiles:

  1. The professional, company-aligned, public-facing version of myself, as well as
  2. The experimental, personal, behind-the-scenes version that enjoys the freedom to branch out into diverse ventures, industries, and projects

If your business is making you gun-shy to pursuing certain opportunities, launching diverse projects, or building new audiences, you may want to do what I didn’t and build a separate public profile for that very expression. You didn’t escape the 9 to 5 just to be a slave to your own business, and there’s no reason you have to.

As you build your businesses, you’re bound to make a variety of mistakes. That said, you’re also bound to stumble upon new skills, opportunities, and achievements you’d never imagined. Unfortunately, it’s far too easy for us to remember only the major setbacks and a few of the outsized successes, mentally glazing over or discarding the tiny victories along the way.

Why in the world should you waste your time recounting your microscopic victories or marginally evolved skill set if you aren’t padding a resume or hunting for jobs? Simple: because there’s so much value in what you’ve learned and accomplished.

By documenting your process, you can do any or all of the below:

  • Easily delegate those newfound skills and tasks to accelerate your company’s growth and minimize your hands-on involvement
  • Offer those skills as additional consulting or freelancing opportunities, enabling you to further monetize what you’ve learned and built
  • Create digital products, services, and entire passive income streams around those skills, thus bolstering and diversifying your cash inflows

Despite running multiple companies and avoiding one-on-one consulting gigs entirely, I’ve made 6+ figures in largely passive income off the competencies I’ve gained along my entrepreneurial journey, and that’s with virtually zero marketing around those skills.

It’s no secret that I’ve built multiple digital businesses largely without social media. Between SEO, email marketing, partnerships, and targeted paid advertising, there are plenty of alternative lead generation tools and platforms. However, that doesn’t mean I’d rewind the clock and do the same.

I also know multiple 6, 7, and 8+ figure entrepreneurs who’ve built ad-free, high-margin businesses solely off the social media audiences they’ve cultivated over the years. The key to their success? It was twofold:

  1. Being early
  2. Being right

I know that sounds like a cop-out response, but let me break it down:

We’re almost all going to be later than we’d like to the platforms we think we need. Thus, most entrepreneurs do one of three things:

  1. Shirk social media entirely, assuming they’re too late
  2. Attempt to pay their way to the front of the line (spoiler alert: it doesn’t always work)
  3. Keep an eye out for the next trending platform and go all-in on the latest bandwagon before it blows up

If we all had a magic wand, of course we’d wave it and morph ourselves into the earliest adopters of YouTube, Instagram, Twitter, etc. Since we can’t do that, the next best thing is to be a bit more judicious about our chosen time, platforms, and contributions.

In retrospect, I’d implement a three-pronged strategy and stave off paid ads for as long as possible:

  1. Where are they now? I’d commit to a consistent (daily) free content marketing strategy on the platforms where I know my audience hangs out, even if I am late to the party. Instead, I let my late adopter status talk me out of ever showing up. While I found alternate methods of lead generation and marketing, I probably passed up on significant free audience cultivation and organic sales.
  2. Early birds still exist. Secondly, I’d dedicate a portion of my time to pursuing a newer platform, even if it’s so far unproven in my industry. Some people flocked to Clubhouse, loved it for a minute, then flamed out. Others built their own businesses within the platform and carved out niches they dominate, simply by nature of being one of the early and dedicated few. Why not throw your hat in the ring and create your own in-app authority? I didn’t make the time, but I wish I had.
  3. Close the wallet. Finally, I’d keep all the social media content marketing free and organic. Once you start paying for reach or engagement, you enter a slippery slope that’s unlikely to release you unscathed. There are plenty of marketing tools and tactics you can pay for, but expanding your social media audience doesn’t need to be one — at least not at the beginning.

Go to Publisher:

Entrepreneur's Handbook – Medium

Author: Rachel Greenberg