She's That Founder: Business Strategy and Time Management for Impactful Female Leaders

033 | How to Not Fail in Your First Year in Business: The Importance of Business Strategy & Time Management

• Dawn Andrews • Episode 33

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Ever wonder how some startups effortlessly dodge the blunders of their first year while others struggle to stay afloat? Are you curious about the secrets behind transitioning from the corporate world to the entrepreneurial race with finesse?

In this insightful episode, I will take you through the pitfalls to avoid in your first year of entrepreneurship. With a rich blend of wisdom, humor, and personal anecdotes, we will dive into the five rookie mistakes that new founders commonly make and how you can seamlessly sidestep them to set your startup on a path to success. 

In this episode, I share:

  • How to embrace imperfections and avoid the trap of overthinking.  
  • The importance of engaging with potential clients through active listening.
  • Why financial prudence in your startup's early days is necessary.
  • My secret weapon for keeping your vibes high when launching a business
  • The bonus mistake (#6) too many new entrepreneurs make.


This episode at a glance:

[03:22]  Don't wait on perfect conditions for success to happen. Just go ahead and do something. Because while you're out there waiting for the mythical ideal moment, other moguls are making moves.

[05:15]  Stretch every dollar and ask yourself if the spend that you're about to make will likely lead to sales in three steps or less.

[06:17]  So the strategy not only guides you but also builds confidence so that you can face the ups and downs coming because you're an entrepreneur. 

[06:39]  None of us is great at everything, especially when it comes to business. We need to improve and find people who are better at things than we are.

[9:13] Corporate may have rewarded you for playing safe, but entrepreneurship is like jazz mixed with a bit of speed metal. You improvise, adapt, and dance to the change of the beat at high speed.


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My Good Woman
Ep. 33 | How to Not Fail in Your First Year in Business


Dawn Andrews:

Ever wonder how some startups effortlessly dodge the blunders of the first year while others struggle to stay afloat? Are you curious about the secrets behind transitioning from the corporate world to the entrepreneurial race with finesse? Well, then stay tuned to avoid the pitfalls of the first year of entrepreneurship and make year one of your new business unbeatable. Let's do it.

Hello, friends, welcome to My Good Woman, the podcast for new and future female leaders. I'm your host, Dawn Andrews, a happily married hockey mom, and the founder and CEO of Free Range Thinking Business Strategy Consulting.

Grab a seat at the table with me each week for candid conversations with culture shifting, glass ceiling busting, trailblazing women leading impactful enterprises. We discuss what makes them tick, how they get it all done, and actionable strategies to help you lead with confidence and grow the visibility, reach, and revenue of your business.

We're classy ladies, but we don't bleep the swear words. Listener discretion is advised.

Well, hello, my good woman welcome to a roadmap episode. These are the episodes where I give you just steps, milestones along the road to look out for, to make your journey in business a little bit easier.  And today I've got the insider scoop, the personal scoop on sidestepping those first year business pitfalls and propelling yourself forward with purpose and passion.

And if you haven't met me yet, I'm Dawn Andrews, founder of Free Range Thinking Business Strategy Consulting, where we help founders become CEOs and corporate execs to become founders. In this episode, you'll learn the five rookie mistakes new founders make and how to seamlessly sidestep the pitfalls on the way to startup success.  And I'm sharing these with you because I have made nearly every single one of them, some of them multiple times, and some of them in a big, old nasty way. 

Thankfully, it didn't cost me my business, but it drastically slowed down my progress at the beginning. So I hope you will learn from my mistakes and benefit from my solutions. Like swift decision-making, human centric marketing, market intelligence, and keeping a tight hold on those dollar dollar bills during your early business days. This is the very essence of entrepreneurial resilience and it ensures that you not only navigate, but thrive in your first business year. 

Hey, future moguls! Are you drowning in the startup hustle? We've got your life vest introducing the ultimate startup checklist. Everything you need to kickstart your dream venture. No more guesswork, just simple steps to business brilliance. Go to DawnAndrews.com/Startup and start checking things off your business growth list today. 

Welcome back. Let's dig into those five rookie mistakes startup founders make and what to do about them.

Mistake number one, overthinking. 

If you're stuck in analysis paralysis, you got to snap out of it. And I have to remind myself of this on a daily basis. The universe isn't waiting for stars to align for you to move your business forward. Make a decision quickly and then change it slowly refining as you go. In the words of life, coach Dan Miller, don't wait on perfect conditions for success to happen. Just go ahead and do something. Because while you're out there waiting for the mythical perfect moment. Other people are making moves. And when you're running a business, momentum is your BFF not perfection. 

Mistake number two. Flying blind.

You may or may not know about my love affair with Chat GPT, which I adore. And that is for another episode. But guess what? Chat GPT doesn't have all the answers about your clients. Oh, shock. Horror. Real deal intelligence comes from you guessed it, real people. 

You don't just jump into the deep end without knowing how to swim and checking with a lifeguard. And knowing how to swim in the lifeguard are represented by your future clients. So dive into market intelligence and by this, I mean, real intelligence, really talk to people, to actual humans, most particularly those that would be your ideal clients. 

I know at the beginning when you're just getting started, it can feel scary and awkward. I resisted it like crazy. But it is so necessary. And if you understand their needs, pain points and aspirations, that human touch will give you insight that no market report, Google search or AI prompt ever could and the best part is that it makes selling and service creation so much easier. 

Mistake number three. Fancy pants spending.

Do you want to know the first thing I bought when I started my business? I had a rotary phone y'all I, I know I've told you that story before, but the first thing I bought when I started my business was a Herman Miller desk chair. Was it my best investment? No, it was not though I will say I am literally sitting on it to this day and it's 22 years later. So do invest in a good desk chair just maybe not first thing. 

Remember when you were interning and counting pennies. I remember those early days in college, or especially when I first moved to New York city. I ate more pasta and ramen than I care to remember. And year one in your startup is like that but with even more pasta and a few more gray hairs. No, you don't need the ergonomic chair or the shiny new website. You don't need all the trappings of a successful business. You just need to connect with people. And you need to stretch every dollar and ask yourself if the spend that you're about to make will likely lead to sales in three steps or less. 

You can barter services if possible, scout for free tools. Spend a lot of time learning on Google if you need to develop new skills. But during those initial 12 months, while you're carving your niche and you're hunting and hustling for sales. Every penny saved is definitely a penny earned. 

Mistake number four. Not doing your homework. 

When I was younger, things came relatively easy to me at school. So I often didn't really work very hard on my homework and it kicked me in my patootie when I got into business. Because you really got to do the work. You can't avoid it or work your way around it. So when I say, do your homework related to your business, what I mean is do some market research. Validate your idea, understand your competition, and start to craft even a basic business strategy.

 And this strategy doesn't have to be insane or detailed. All you need is to decide who you're serving, how you're serving them and how you're going to make money. Strategies can be really simple, especially with an early stage service-based consulting business. You're not trying to submit your business proposal to a bank, or probably not at this point and probably not to investors either. 

You're just getting started using your own capital. And that initial strategy doesn't just guide you, but it builds confidence so you can face the ups and downs that are coming because you're an entrepreneur. A little business strategy now means fewer face plants later. 

Mistake number five. Being the wrong kind of know it all. 

Entrepreneurship often requires wearing many hats and a big old dose of humility. None of us is great at everything, especially when it comes to business. We need to improve and we need to find people who are better at things than we are. So spot those skill gaps early on and fill them.

And then find your entrepreneurial gang. Do things like attending workshops or taking online courses, find somebody to follow that's doing the same kind of work that you're doing, and track them and learn from them. I can't tell you how many email lists I subscribed to in my first year of business.  So join their email lists and when it comes to your people, join communities or masterminds so that you can find peers that are in a similar place or even a few steps ahead of where you are in building your business.

Share experiences find accountability partners. So you can collectively navigate this transition and the early stages of growth. I don't want you to be on this ride alone. So why not celebrate? Or scream and pull your hair out together.

Okay. Those are the five rookie mistakes that startup founders make. And here's a bonus mistake for you.

Mistake number six, Staying corporate.

Corporate may have rewarded you for playing safe. But entrepreneurship is more like jazz mixed with a little speed metal. You improvise, adapt and dance to the change of the beat at high speed. What I'm saying is you need to embrace a growth mindset. Ups and downs are 100% guaranteed, my friend. 

And if you can start to see the setbacks as lessons instead of failures, you'll be just fine. Resilience is your secret weapon, and every bruise is a badge in the business world. And I know you might be quaking in your boots as you launch your business. But every venture corporate or entrepreneurial has risks, and we've got you. 

Today, we talked about jumping in without overthinking no more analysis paralysis. We talked about getting words straight from the people who matter most; your potential clients. We talked about being a penny pinching pro in the first few months. And we threw in some gems about getting your homework done, leveling up your skills and keeping your vibes high. 

Slip ups might happen. For real, they will happen. But with this knowledge up your sleeve, you'll bounce back better than ever.  And if you'd like to hear more about the real deal behind the scenes of getting started. You can hear my warts and all story in Episode 28, CEO or Bust. 

Thanks for joining me today. If this episode resonated with you, DM me at freerangethinking on Instagram with the word rookie. I know you're out there and I want to throw you some love and support. Remember to stay curious, stay fearless and keep making bold strides in building your new business. 

See you next time, my good woman.

Thank you for joining me this week. To view the complete show notes and all the links mentioned in today's episode, visit mygoodwoman.com. And before you go, make sure you follow or subscribe to the podcast so you can receive fresh episodes when they drop. And if you're enjoying my Good Woman, leave us a review on Apple Podcast reviews are one of the major ways that Apple ranks their pod. So even though it takes only a few seconds, it really does make a difference and helps our show grow.

This episode was produced by me and Julissa Ramirez. Thank you again for joining me, Dawn Andrews, in this episode of My Good Woman.