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How to Support the Entrepreneurs and Side-Hustlers in Your Life

How to Support the Entrepreneurs and Side-Hustlers in Your Life

“There’s no opportunity just to coast,” one of my clients once said to me. “It’s really hitting me that if I’m going to make money– pay my rent, pay down my credit cards, all that– it’s all on me.”

As my client said this, I could hear the fear in her voice. 47% of people became entrepreneurs because they wanted to be their own boss. The seemingly obvious but often-overlooked flipside of being your own boss is that you are the boss, and your ability to succeed is entirely on your shoulders.

What my client was getting at and what we talked through for nearly an hour was that it can be incredibly lonely when you’re getting started as an entrepreneur. Most new entrepreneurs do not have the cash flow and capital to hire a team to assist them, so they end up working long hours on their own. Often, they’re working on all the things around their core product or service– the marketing material, sales strategies, website management, social media– that they’re not as passionate about or don’t feel as confident in.

Adding another layer of challenge into the mix, when entrepreneurs look to their friends and family for support, they may get lackluster responses or reactions that suggest they’re being judged or criticized for not being sensible or practical enough.

Nothing takes the wind out of your startup sails quite as quickly as excitedly explaining your ideas to someone you deeply respect, only to have them give an unenthusiastic response.

And it’s a pity that that’s the case. According to the Global Entrepreneurship Monitor, in 2022, 71% of entrepreneurs pursued entrepreneurship because they have a desire to make a difference in the world.

Our economy and communities need more budding challengers that diversify offerings and keep money local. So, here are some ways you can contribute by supporting the entrepreneurs and side-hustlers in your life.

Understanding the Entrepreneurial Mindset

People who are drawn toward entrepreneurship are often unconventional thinkers who value independence and innovation over convention. They’re prone to asking what if and thinking in terms of bets. Where most people see frustration or complexity, entrepreneurs see an opportunity.

If you think differently, preferring stability and predictability over independence, it may be difficult to see eye to eye with entrepreneurs when it comes to things like the degree to which having a predictable salary is important.

What’s important to keep in mind is that for entrepreneurs, money is often of secondary importance to doing the work. A common theme among the entrepreneurs who I’ve worked with and mentored over the years is that they get as much satisfaction out of figuring things out and solving complex problems as they do making money from their work.

It’s also worth noting that just as you may have difficulty understanding an entrepreneur's risk vs reward perspective, many entrepreneurs struggle to understand and accept more traditional employment paths. For plenty of entrepreneurs, the goal is to create a work life that’s flexible and molded to their values and plans as opposed to having a job that dominates their life, allowing them to truly live in the moments between work shifts.

Even if that type of lifestyle is only aspirational for early-stage entrepreneurs, it’s still a powerful, compelling motivator in how they see the world.

The Challenges Entrepreneurs Face

Understanding how entrepreneurs view the world differently is part of the equation for figuring out how to support them. The other key aspect is understanding entrepreneurs' challenges and better understanding what likely contributes to their stress and frustrations.

Cash Flow Is the Biggest Challenge

According to a recent study by Intuit, more than two-thirds of small businesses (68%) surveyed say they have cash flow problems. Inflation drives up these concerns even more, with the cost of doing business and making ends meet often ballooning faster than new entrepreneurs can drive revenue. If someone doesn’t have deep pockets before pursuing entrepreneurship, they may feel like starting their own business isn’t even a feasible reality for them.

Budding entrepreneurs still need to be able to meet their needs and have enough of a budget to promote their services online, hire help when appropriate, and manage inventory, workspace rent, and more.

That’s one reason side hustles often precede full-time entrepreneurship: it’s a bit easier to focus on creating a sustainable business when you’re able to keep a roof over your head and food on the table. But, that also contributes to the second challenge entrepreneurs face…

Entrepreneurs Are Consistently Spread Thin

Entrepreneurs have to do everything on their own, especially in the early stages, where they may not have much- if any- formal support or employees. This is often overwhelming, especially if someone hasn’t done it before. This includes:

  • Building and launching a website to connect with prospects.
  • Establishing a social media presence.
  • Filing for incorporation as an LLC, S-Corp, or similar.
  • Doing bookkeeping, filing quarterly taxes, and staying in the Department of Revenue’s good graces.
  • Prospecting and connecting with potential clients.
  • Orchestrating marketing campaigns.
  • So. Many. Emails. And. Phone. Calls.

And that’s all before they actually get to do what they set out to do in the first place. This becomes even more of a headache when you consider that these are tasks many entrepreneurs have to handle on top of their day jobs, family obligations, and taking care of themselves.

Many Entrepreneurs Lack Formal Education in Their Field

It would be one thing to handle all of the responsibilities that come with the territory if entrepreneurs could do them on autopilot– if the myriad tasks on hand didn’t require focus or thought to be knocked out.

The reality, however, is that many entrepreneurs lack formal education in business or their chosen field before going into business. According to a recent article by HubSpot,

  • 30% of entrepreneurs have a high school diploma as their highest degree.
  • 31% of entrepreneurs have an associate's degree.
  • 17% of entrepreneurs have a bachelor's degree.
  • 18% of entrepreneurs have a master's degree.
  • 4% of entrepreneurs have a PhD.

As someone who comes from a rural area with a relatively low representation of people with post-secondary education, I’ve seen first-hand how these statistics play out in the entrepreneurial landscape. We don’t believe that formal education and degrees are necessary for entrepreneurial success, but it is worth calling out that when you lack formal training on a subject, each time you tackle it, you’re essentially having to learn a new skill until you eventually get the hang of it. And government entities in the US don’t make it easy to learn how to do things by the book.

Standing Out is Increasingly Difficult (and Expensive)

The dream scenario for most entrepreneurs would be making a few descriptive blog posts and social posts and having The Algorithms™ take that content directly to your target audience, who then gets super enthusiastic and coverts. The millions start flowing in in a few days or weeks.

But that dream is rarely– if ever– realized. It’s a rude wake-up call for most entrepreneurs that they’ll spend more time promoting their business and acquiring customers than actually conducting their business.

SEO, once the king of low-cost traffic to a business website, is becoming a more complex field to navigate, especially for a beginner. Search engines like Google rely heavily on Experience, Expertise, Authority, and Trustworthiness (EEAT) signals to determine what should rank and perform well on their services. For a brand-new business that hasn’t had a chance to prove itself yet, there’s not much for search engines to key off of to know that their business should be visible.

Beyond that, paid advertising is increasingly expensive and has a high barrier to entry. The Internet was once viewed as a democratizing force that allowed anyone to compete on equal footing with big businesses, but when a successful ad campaign can cost thousands of dollars per day, it becomes clear very quickly that the online ecosystem favors those with deep pockets, which means large, well-funded businesses have the upper hand. Plus, your average entrepreneur with a Canva subscription isn’t going to be able to create ads of the same quality as their much wealthier competitors.

Even organic social media content is becoming more difficult to get in front of the right audiences. Social media networks prioritize engagement and time on the platform because that’s how they make revenue. As a result, the content that algorithms tend to surface most often is inflammatory, polarizing, hyperbolic, or part of a sponsored post. Facebook has revealed that a user profile's average news feed story reaches just 12 percent of their friends.

Doing Everything On Your Own Can Be Very Isolating– Especially When You Can’t Easily See the Payoff Of Your Efforts

I’ve observed a common trajectory for budding solopreneurs in which they kick off their efforts full of vim and vigor only to fizzle out after a few weeks or months. Speaking to such entrepreneurs, one of the common themes that emerges is the notion that they were burning themselves out and not getting enough feedback, validation, or ROI to make it worth continuing.

Being an emerging brand is tough, and it can take months of consistent effort before your business starts to see results. Even entrepreneurs with a long-term mindset at the beginning can quickly become overwhelmed by short-term realities and feel defeated. I often see this in people who are bootstrapping or trying to do everything on their own to become profitable before they hire.

Getting a new business off the ground can feel like several months of beating your head against a wall (or, at least, your keyboard). It’s inherently frustrating, but it becomes very isolating as well when entrepreneurs consistently exert themselves and push the boundaries of their skill set only to get back lackluster results. It runs the risk of starting a spiral of self-doubt in which you ask yourself if you’re good enough, smart enough, or competent enough to do what you want.

Practical Ways to Support Entrepreneurs

Those are the daily challenges faced by entrepreneurs. So, how do you meaningfully support the entrepreneurs in your life? What’s that next step up from a clap on the shoulder and a hearty you got this?

To best help an entrepreneur, I recommend thinking like… an entrepreneur.

A good entrepreneur looks at the problems in their target audience’s life and sees that as an opportunity to craft a solution. You can do the same to support the self-employed folks in your life. Take the challenges they face and flip them on their head.

Talk About What They’re Doing- Word of Mouth is King

Something anybody can do to help out a small business or entrepreneur in their life is to talk about that business and recommend it to friends, colleagues, and other connections.

It may sound silly, but that is genuinely one of the most impactful things you can do. Word of mouth is king when it comes to getting a business off the ground and in front of customers.

  • Boston Consulting Group estimates that word of mouth is 2 to 10 times as effective as paid advertising.
  • McKinsey & Co reported that word of mouth is the primary factor behind 20-50% of all purchasing decisions.
  • Nielsen found that consumers were 77% more likely to buy a product if their friends recommended it.

People don’t want to buy from ads and brands. They want to buy from people. They want to trust that their hard-earned money isn’t being flushed down the drain. Plus, people are skeptical of new brands. Large cohorts of the population will turn to Google after seeing a business’ ad for the first time and search “Is [BUSINESS] legit” before considering making an order.

So, when people get a personal recommendation or endorsement from someone they trust, it makes a huge difference in that business’ ability to connect with its customers.  Be an evangelist for your friends and family.

Bonus: Word of Mouth is Best When Speaking to the Right Audience

You are going to have the most impact on a business's future success by spreading the word to the right audience. Not every business is a good fit for every consumer and vice-versa. If you know an entrepreneur’s target audience and have access to people in that audience, talk to them directly.

On the flip side, not knowing people in an entrepreneur’s target audience shouldn’t stop you from spreading the word. In a community, we’re all just a few degrees of separation from each other. If an entrepreneur’s target audience is farmers and SMBs in the agriculture space, but you don’t know any farmers, chances are that you know people who do. Your friends, your church group, your sports league, your neighbors all have the potential to be more closely linked to someone in the target market. If you tell them about what a small business does or offers, they have the potential to pass that information along.

Help them Build a Support System

If you have the skillset and the extra time, volunteering to help out with a complex or tedious initiative can be huge. Many entrepreneurs will be hesitant to ask for help when they need it, so if it’s something you offer without them asking, they’ll probably leap at the opportunity.

However, if you’re not in a position to directly contribute, you can still help by encouraging or helping facilitate the creation of a support system.

This can take a few forms. Making introductions to potential mentors, investors, collaborators, or customers is always going to be welcome and helpful.

(If you know potential investors who are interested in funding steady, workhorse businesses in the professional services space, I would also appreciate that introduction).

Beyond that, you can also encourage the solopreneur in your life to connect with others in a similar position. We’re biased, of course, but we recommend sending them over to sign up for the Howdy Curiosity Community, where we:

  • facilitate collaborative learning between entrepreneurial peers,
  • host quarterly book clubs,
  • offer access to exclusive discounts,

and so much more– all for an affordable monthly or annual fee.

But, if that’s not quite their speed, there are also great resources like Y Combinator’s Startup School, which is particularly valuable for entrepreneurs entering the tech and high-growth space. Your local Small Business Development Center (SBDC) likely also offers workshops and community gatherings for entrepreneurs in your area that may be worth checking out.

Contribute To (or Promote) Funding Efforts

As we mentioned earlier, early-stage cash flow is often the deciding factor between whether an entrepreneur stays in business or not.

It takes a huge amount of courage for a business owner to ask for help funding their business. If they open a GoFundMe or similar, contribute what you can to it, even if it’s only a few dollars.

In the small business world, funding is elusive. It can often be a catch-22 to get funded. While plenty of banks and entities will fund a business, they often require you to have been in business for at least a year (or longer) and already be making significant monthly revenue before you can access a small business loan. But in order to be in business that long and generate revenue, you often need capital to get started.

There are also angel investors in the business world– individuals who invest in a business, typically in exchange for equity (a percentage of ownership), but angel investors often prefer to invest in high-growth opportunities. So, if someone is starting a business with the intention of being stable and having a strong local presence but not rapidly scaling to tens of millions in revenue any time soon, angel investors are going to back out.  

Starting a business is often exalted as an equalizing opportunity in the United States and is part of the Self-Made Man ethos that has become part of the American identity; in reality, those who can afford to be “self-made” are often already independently wealthy to begin with.

As a result, a lot of budding entrepreneurs have limited options for accessing the startup capital necessary to get their business off the ground.

  • They may use their income to offset or fund their operating expenses if they also work a standard employment job.
  • They may use high-risk, high-interest personal loans or credit card debt as capital.
  • They may turn to crowdfunding or other fundraising efforts.

Turning to crowdfunding may feel humiliating or terrifying, so if someone in your life launches a crowdfunding attempt for their small business and they’re someone who instills within you a sense of confidence, contribute what you can and then share the effort with your network, preferably with a personalized message about why you’ve donated and why others should as well.

Supporting Entrepreneurs and Small Business Supports Our Communities

When you support a small business or an entrepreneur, the impact you have can extend far beyond that single interaction.

Small business success and growth help keep money local. It puts cash directly in the pockets of members of your community as opposed to further inflating the cash reserves of mega-corporations like Amazon and Wal-Mart. Doing so is a necessary step toward tackling inequality and, especially in rural communities, the deflated pay and perceived lack of opportunity that keep people in poverty.

In an economy where so much of what we do is dominated by an ever-dwindling number of mega-corporations, supporting small and independent efforts– in whatever form of support that takes– is a radical act of choosing to buck trends and support the communities that need it.  

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