7 Challenges Every Bootstrap Entrepreneur Faces

The entrepreneurial experience is one of duality, a paradox, that’s both exciting, full of hope, and, anxious, stymied by fear. Two very different states of mind and emotion, however, in the majority of instances, one set is preceded by the other. It comes with that spark of the proverbial, “ah ha!” moment–excitement and genuine, heartfelt belief that whatever it is, it will work. Often, this elation is short lived and it’s little wonder why.

We grow-up with expectations and more than enough are not fulfilled. So, we learn skepticism, caution, and to examine our actions before blindly leaping. This is precisely why extreme success stories remain so unfathomable–often accompanied by the phraseology, “against all odds.” These sets of circumstances cause us to look at those odds and be honest about the entrepreneurial journey, which more often than not, requires a lot of work, much dedication, and, the ability to see and believe what others don’t.

7 Challenges Every Bootstrap Entrepreneur Faces

When you start your own business, it might be a side gig, something that only takes a few hours out of your week and is intended to grow incrementally. It could also be the resort of finding yourself suddenly unemployed and the opportunity to take control of your own future provides all the drive necessary to start and never look back. Others partner together and use old fashioned sweat equity to get their businesses off the ground. Whatever the case might be, there will be obstacles.

Regardless of size, most businesses face many of the same challenges every day. Maximizing profits, minimizing expenses and finding talented staff to keep things moving seem to be top challenges for both SMBs and large corporations. —Entrepreneur.com

It might come as a surprise, but new companies fail for two primary reasons: too little business, and, too much business. In the former instance, there’s obviously a lack of revenue; but, the latter seems counterintuitive, perplexing, though perfectly explainable–overwhelming demand. These dynamics are usually out of the company’s control but there are others, and, just one of these can be enough to cause failure:

  • Stability. While you might have a marketable and sellable idea, possess the talent to sell it, and have enough resources to get it out there, you don’t control the economy. Being employed provides a sense of security, though arguably, it’s a false one. There is no guarantee your vision will come to fruition in the way you now imagine it, or, at all.
  • Income. It’s a fact that many entrepreneurs don’t take any salary for the first several months, even for a year or more, because the money’s better spent rolled back into the business. Having to forego a steady income, even temporarily, can be too much to bear for some, it’s looking to the future and taking stock of gains that provides the remedy.
  • Sustainability. The marketplace changes and some businesses become near or completely obsolete. In the wake, new opportunities emerge, but that doesn’t undo the damage suffered by those caught on the wrong side. Pivoting when times begin to change is a necessity to embrace.
  • Comfort. One thing that seems strange is what’s obvious by its absence–being the boss. Sure, it will be you who’ll be in charge, which means you will be making the tough decisions, you will be the one responsible for company mistakes, and you who must put your foot down.
  • Schedule. Your work and personal lives will intersect many times during your startup period and here again, it’s because you’re the boss. While you’ll have set boundaries, you’ll have to do so smartly and be flexible.
  • Sleep. Lying awake, brainstorming, putting in a lot of extra hours to get something done, having to meet this deadline or be present for a meeting, all of these are common. Try to find a schedule that largely works and take advantage of downtime.

Seventh on the list is confidence, and, it’s among the most powerful of influencers. Your confidence will be challenged many times, but this just comes with the territory. You will have doubts, falter, and make miscalculations, but these are only as hurtful as you allow.

Finally, if you have a viable business model with a demand for a product or service, then much of your success falls on you ability to persevere. Many businesses fail or fall “three feet from gold” because the entrepreneur quit. In the toughest of times, I encourage my clients, as I did for myself, to take Action every day on something that will help to grow your business. Sitting, worrying or praying does no benefit without Action. And, Action helps to resolve anxieties and fear.

So, go out and pursue our dream today, and take Action every day to building your business!
[shareaholic app=”follow_buttons” id=”26833294″]

Like this article?

Share on Facebook
Share on Twitter
Share on Linkdin
Share on Pinterest

Related Posts

Genesis Landscape Solutions photo

How Genesis Landscape Solutions Tripled Growth by Building Real Infrastructure

.elementor-widget-text-editor{font-family:var( –e-global-typography-text-font-family ), Sans-serif;font-weight:var( –e-global-typography-text-font-weight );color:var( –e-global-color-text );}.elementor-widget-text-editor.elementor-drop-cap-view-stacked .elementor-drop-cap{background-color:var( –e-global-color-primary );}.elementor-widget-text-editor.elementor-drop-cap-view-framed .elementor-drop-cap, .elementor-widget-text-editor.elementor-drop-cap-view-default .elementor-drop-cap{color:var( –e-global-color-primary );border-color:var( –e-global-color-primary );} Warren Wheat wasn’t new to landscape maintenance — he’d already built and sold one company in the industry before the entrepreneurial itch brought him back in 2012 with Genesis Landscape Solutions. What started as a request for help writing better commercial proposals turned into something much bigger. “Since hiring John and his team three years ago, our company has experienced more than 3X growth. During that same period, our profit margins have also risen significantly,” Warren says. “John is an extremely well-rounded consultant that has the ability to adapt and customize his approach in order to fit the specific needs of your business… As the President of a company with over 120 employees, I genuinely appreciate the partnership we have formed with John.” From a Better Proposal to a Bigger Question Warren originally reached out to Waters Business Consulting Group for help putting together a more comprehensive, professional proposal he could submit for large commercial maintenance opportunities. That work naturally expanded into a website overhaul and refined marketing to support a more cohesive brand. But partway through, Warren admitted something bigger: he knew he was at or near capacity in the business’s current state. A sharper proposal and a better-looking website were great, but they didn’t solve the real question — how could the organization actually grow and move to the next level? That reframe pointed to deeper gaps: the business needed a clearer understanding of its current model and what was driving top-line revenue and margins, a real roadmap of growth objectives, and the organizational infrastructure to support scale. That meant building out organizational structure, hiring high-caliber talent to form a cohesive team, and continuing to sharpen marketing across proposals, website, and presentations. Building the Infrastructure for Scale Waters Business Consulting Group worked with Warren’s leadership team to rebuild the business model around its highest revenue-generating services and activities, collaborating with outside experts on web design and the new professional proposal that had started the engagement. The team helped build a more balanced portfolio of work to support profitable growth, and analyzed direct costs closely to protect and improve margins as the business scaled. Just as important was the human side of scaling: key stakeholders were brought into meetings to increase buy-in and develop leadership within the organization, and a formal organization chart prioritized hiring for the roles the business actually needed, with clear operational responsibilities and KPIs tied to compensation. The employee recruiting and onboarding process was refined to consistently find the right people to support growing properties and workflow. The Results — and What’s Next The changes gave Warren something he hadn’t had before: a predictable business model that let him see where the company was heading proactively instead of reacting to whatever came up. Clear processes and procedures with real accountability metrics replaced guesswork, the team gained a shared understanding of goals and revenue targets, and direct costs and overhead came under real control through internal tracking systems. Leadership strengthened at the upper levels of management — all of which supports the more than 3x growth and rising profit margins Warren describes over the engagement. The work continues, too, with new technology for weekly property reporting and GPS employee time tracking, a more proactive recruiting and retention strategy, a refined and more profitable irrigation division, formal career tracks and compensation plans for key positions, an updated policy and procedure manual, and a new CRM solution to improve customer retention alongside ongoing leadership development training. If your business has outgrown its current systems but you’re not sure what infrastructure to build next, that’s exactly the kind of scaling challenge Waters Business Consulting Group helps owners solve. Schedule a free consultation to map out what’s holding your growth back. Contact Waters Business Consulting Group

Read More »
Waters Business Consulting Group

Don’t Dare Make these Startup Customer Service Mistakes

Your business exists because of your customers, and how you treat them will determine whether they stick around—or tell ten friends about the bad experience they had with you. Too many startups focus on sales and growth while treating customer service as an afterthought. Here are the costly customer service mistakes you need to avoid.

Read More »

Imagine Selling Your Business…

How Would Your Life Change?

You didn’t start your business just to stay busy—you built it to create freedom, security, and options for yourself and your family. Selling your business can be life-changing, but the real question is whether you’re intentionally building toward that outcome or simply leaving it to chance.

Sign up below for a free consultative session to learn what your business could be worth today and in the future! 

Thank you for your interest in learning what your business is worth. We will be in touch shortly.