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4 Lessons I Learned as a First Year Entrepreneur Earning 5-Figure Months



There are a lot of messages on how to start and grow a successful small business out there.


There are a lot of good tips, a lot of bad ones, and plenty of conflicting ones.


So how do you sort through them and decide what you actually need to do in order to launch and grow a business that makes an impact, brings in cash and doesn’t burn you out?


When I left my corporate Head of Marketing role to start my own coaching and consulting business, I thought I had the cat in the bag.


I’d managed multi-million dollar budgets, specialized in low-investment but high-acquisition growth marketing strategy, and built brands from the ground up.


But settling into entrepreneurship taught me that bootstrapping your way into generating your own wealth involves unique strategies the corporate and startup worlds don’t practice.

Knowing what I know now, they could probably learn a lot from successful small business owners.


By applying my decade of experience launching and growing businesses, interviewing dozens of small business owners and testing and learning on my own business path, I’ve discovered 4 important guiding principles.


These guiding principles have helped me grow from $0 to consistent five-figure months within just months of launching my first offering.

The following captures those guiding principles that contributed big time to my small business success.


1) The actions you take are more important than the plans you make.


I see it all the time. Aspiring entrepreneurs and small business owners spending months or even years gathering information, taking courses, seeking advice and hoping for an abundance of clarity and preparation before they take the leap.


What few realize is that all of those months and years of preparation come at a cost - all the money you could have been making if you’d been taking action while you were planning away.


From my perspective, there are just a few things you need to know in order to take action on a service-based business.

Your Why - This is your guiding light for making decisions in your business. As the raison d’être for your business, it will help you stay focused and aligned to what you’re passionate about and the impact you want to make. Keeping your business in alignment with your passion and impact is one of the best ways to keep you motivated and help the work feel more like purposeful play.


Your Value Prop - This is the value you deliver to your audience. It’s how you make their lives better in results-oriented terms and how you impact their day-to-day life. I like to get as specific as possible with value props, so people can visualize and experience the impact. For example, “Sleep better” sounds good, but doesn’t quite resonate the way “Fall asleep within 15 minutes of your head hitting the pillow, sleep deeply and soundly without tossing and turning, and wake up ready to seize your day” does.


Your Initial Offering - Your initial offering is all about identifying the simplest way to deliver on your value prop. Identifying it requires hyper-vigilant focus - we all have tons of ideas bouncing around - but landing on that first low-investment, high-impact offering will give you a great starting point to build, pivot and evolve from.

Your Operational MVP - Simply put, this is how you deliver on your offering in the simplest way possible. Let’s say you’re a coach and your initial offering is a two-month coaching package with weekly sessions. Instead of finding a client management platform, setting up a messaging system, and going down the rabbit hole of complex software and sexy systems, you can choose to operate with a Zoom link, PayPal account and Google Drive folder (and then build from there).

Where Your Audience Spends Time - Before taking action, it’s good to have an idea of where your actions will have a greater impact. And the “where” of business action is wherever your audience spends their time. Identify where your current network lives (start with what you’ve got) and where an audience that would benefit from your value prop spends their time, and you’ve got your initial areas of focus.

You don’t need to get caught in the endless cycle of planning and preparing beyond these core items.


You also don’t need to have 100% clarity on any of them or have any of them perfect. The beauty of getting started is that you can then test and learn and pivot from there.

By putting an initial offering out in front of your audience sooner, you’re giving yourself the opportunity to earn income for months, possibly even years earlier than you would have otherwise.


I personally launched my business 4 weeks after I decided on my initial offering. I have pivoted 4 times since and evolved my offerings multiple times.


The experience and knowledge I gained while having a live business helped me plan for what was next each step of the way.


And if I had waited even 3 months to launch my business? I would have missed out on five-figures worth of revenue.


Take action. Plan as you go.

2) Progress isn’t always an upward pointing arrow.


If you look at the income tracker of any new small business owner, you will likely see something that resembles a steady stream of ocean waves.


Said differently, there will be dips.


These are what I call the “ebbs” in the ebb and flow of progress.


We tend to think of success as a consistent day-over-day, week-over-week or month-over-month upward trajecting chart.


We fear that one step backwards means all is lost. We worry that if we lose our upwards momentum it’ll essentially be like starting over again.

This simply isn’t the case.


If you head into entrepreneurship knowing that there will be ebbs, when things feel like they’re receding, and flows, when abundance pours in readily, then you will save yourself a lot of heartache and worry.


Free yourself from the perfectionistic expectation of constant growth, and you will free up a lot of energy otherwise spent worrying. You can redirect that energy into igniting your next flow state.


This is also where you’ll want to keep in mind that you’re not starting over just because you had a low-income month or didn’t sign as many clients as you’d like.

The seeds you planted yesterday will sprout at surprising times, and can often serve as the impetus for your next flow state.

3) Planting seeds is just as important as harvesting your garden.


Every time we watch TV, post something on social media or send a text message, we’re setting ourselves up for a near-immediate dopamine hit.

Given that the world we’re in has us addicted to immediate results, it’s easy to get stuck in a cycle of immediate gratification with our entrepreneurial efforts, too.

When given the choice between spending our time on an Instagram post vs. writing a long-form piece of content, researching podcasts to pitch, or building relationships, a big part of our brain prefers to experience the joy of the immediate Instagram likes.


But there’s a longer-term game here that we want to play, and that’s investing in your business of tomorrow, next month or even next year.


We can’t forget to plant seeds now so we’ll receive surprising and fun gifts down the road.


In the middle stages of my business, I decided to offer a lot of free value to my audience in the form of complimentary decision-making sessions.

I hoped to build relationships with people I hadn’t yet had a chance to connect with and gain their trust.

I delivered on 20+ hours of free sessions in two weeks. Only one of them immediately signed with me.

Fast forward to today, and 50% of the the people I offered value to in those sessions have either signed with me or partnered with me to bring in more business.

If I had gone into that decision-making campaign expecting the return on my investment to be immediate, I would have been deeply discouraged following it.


Instead, I happily invested the time, planted my seeds and now enjoy the bounty of a blooming garden.

4) Your meaningful relationships are more important than the size of your audience.


Rich Litvin is a mentor of mine (the best thing about the digital age is you can have a mentor who doesn’t even know you exist).


His perspective on how to think about your audience resonates with me on a big level.

According to Rich, you can think of all the people in your network and audience as fitting into one of five buckets:


1’s: Your ones do not like you. They don’t like what you have to say. And if given the chance, it’s highly likely that they would say unkind things about your business, serving as big detractors.

2’s: Your twos also don’t like you. But they’re a little less active and invested in their dislike and disconnection from what you have to offer.

3’s: Your threes are pretty neutral when it comes any opinion of you and your business. They could be swayed either way.

4’s: Your fours like you! They resonate with a lot of what you have to say and offer and are happy to receive your messaging.


5’s: Your fives are your super fans. They connect with you, your value, and your business on a meaningful level and pay you money to get more of that value. They tell others how great you are and are active supporters.


The truth is, if you’re putting yourself out there, you likely have people in your audience who fit into each of these buckets.


A side note I’ll offer, is that a lot of times people’s poor opinion of you has less to do with you and more to do with their own projections and subconscious programming, but that’s for another article.


Regardless of the reason, the fact remains that you have 1’s, 2’s, 3’s, 4’s and 5’s out there in the world. And every time you take action with a public-facing message or piece of content, you’re exposing yourself to their varied reactions and responses.

So, if your goal is to attract clients, who should you focus on?

Some people opt to keep their messaging as neutral as possible so as not to “set off” the 1’s and 2’s out of fear that their detractors will chime in. Whether they realize it or not, they’re choosing to play small.

Others spend a considerable amount of time and energy trying to convert their 3’s into 4’s and 5’s in hopes that they’ll become supporters and help spread the word. That’s a lot of energy invested in people who don’t really care.


The most successful business communicators focus 100% of their messaging and relationship building on their 4’s and 5’s.


The people who love you, your value and your business are the ones who are most likely to engage in your offerings, re-engage in your offerings and send others to your offerings.


Rich Litvin says it best - “The people who are most likely to pay you, are the people who have already paid you.”


And in my experience, a referral sent to you by a 4 or 5 is way more likely to become a client than those who discover you without a referral.


The size of your audience doesn’t quite matter as much as the quality of it.


Having 100 4’s and 5’s is more powerful than having 1,000 1’s, 2’s and 3’s.


So when your focus becomes growing your audience, give thought to where your 4’s and 5’s live, and how you can attract them vs. grabbing for an audience that you have to win over.


Attract and nurture your 4’s and 5’s. Forget about everyone else.


Ready to Take Action?


I apply these principles and more in my individual and group coaching programs. If any of this resonated, check out The Business Firestarter group coaching program.