After 20 years together and two successful exits, we’ve learned one undeniable truth when you start your business – for every win, we stepped in sh&t twice. If we’d had a startup business roadmap of what not to do, we could have saved ourselves a lot of stress, sleepless nights, and costly mistakes.
Fast forward to today. With battle scars and hard-earned wisdom, we’re launching our coaching community, Female Mavericks, (and writing a book!) – not just to do it better this time, but to help you dodge the same landmines. Every mistake we’re about to share, we’ve lived. And truthfully? We still screw up, just faster and smarter. The difference now? We see it coming and pivot before it wrecks us.
Mistake #1: Going It Alone
One of the biggest misconceptions in startup life is that you should lean into your strengths. While that’s true, what’s even more critical is identifying your weaknesses, and finding people or resources who can fill those gaps. When you’re in full startup business mode, your focus needs to be on driving the business forward and generating revenue. But we’ve seen so many founders, including ourselves, waste valuable hours struggling with bookkeeping, HR compliance, or operational tasks that could easily be outsourced or delegated.
Early on, build out a skills matrix to map out the areas where you lack expertise – finance, HR, accounting, IT, office management, etc. Once you have identified the areas you need help, seek out resources – it could be a new hire, independent contractor or even bartering services. It doesn’t matter how you do it, but do it…we guarantee it will change the dynamic of your business (and probably your mindset to keep pushing forward!).
Mistake #2: Fearing Failure
You miss 100% of the shots you don’t take. And yet, so many entrepreneurs let the fear of failure keep them from taking those shots. Here’s the truth, you will fail. Sometimes in small ways, sometimes in big, gut-wrenching ways. But failure itself isn’t the problem, the real problem is if the fear of it paralyzes you or makes you too conservative.
Every successful entrepreneur we know has had missteps, including us (lots of them actually). The difference is that they (and we) get back up, tweak the strategy (or, in some cases, scrap it entirely), and try again. Our first startup business idea wasn’t flawless. Neither was our second. But each one taught us something we needed to know for the next stage of our journey. The sooner you embrace that fact, the better.
Mistake #3: Underpreparing
We try to never walk into a meeting – whether it’s a sales meeting, client meeting, investor meeting, new hire interview (you get the picture) – without knowing exactly what we want to communicate and what we hope to learn. Preparation is everything. When you are running at 150 mph, it’s easy to bounce from one thing to the next without even so much as a breath, but each touch point comes with an opportunity, so don’t half ass it. (It still stings knowing we lost a piece of business a few years ago because the CEO liked us but didn’t think we did a “deep enough dive” into the company’s stock decline for him to get comfortable with us. Ouch.)
Regardless of the situation, focus on building a personal connection first, maybe it’s a shared alma mater, a love of travel, or even something as simple as parenting young kids. Then, for sales and partnership meetings we would quickly turn to what sets us apart and make sure we introduce one transformative idea that will stick with them long after the meeting ends. We approached investor meetings the same, but the end game was different. Instead, our focus was on the ONE (just one) untapped, biggest opportunity in our business that funding would unlock. Irrespective of the type of meeting it was, we strived to go in with three key points we wanted to get across, and made sure we landed them. (And then, desperately tried to shut up to hear the response.)
If you can’t sum up your message concisely, your audience won’t remember it. And if they don’t remember it, you’ve wasted your shot.
Mistake #4: Ignoring Startup Burnout
Burnout doesn’t happen all at once, it creeps in gradually. It starts with a constant mental checklist of everything you didn’t get done that day, the weekly to-do list that only gets longer, the endless cycle of competitor research, and the sting of losing a pitch to a rival. And before you know it, you bring all that stress home. You’re anxious, irritable, exhausted, or just completely checked out.
We’ve been there and still are sometimes. But we’ve learned that stepping away, even briefly, isn’t just necessary; it’s essential. Just this morning, Beth told Victoria, “Sorry I didn’t answer your texts yesterday – I was spending time with Ava.” And Victoria’s response? “Yes! How was it?” Victoria stepped away this past weekend with three basketball games, three soccer games and a cheer competition and Beth’s only question on Monday morning was, “did you survive the weekend?”
Startup life often feels like The Hunger Games but trust us, walk away for a bit. Spend time with your partner, your kids, or just yourself. The work will still be there when you get back, and you’ll be in a much better place to tackle it.
At the end of the day, mistakes aren’t just part of the startup business journey – they are the journey. Every wrong turn, every faceplant, every “how the hell could we have done that?” moment has shaped us into the entrepreneurs we are today. Spoiler alert – no single mistake (or even a long series of them) ever killed the business. And, the business didn’t go bankrupt when we both took vacations at the same time. So go build, take risks (and vacations), screw up, learn, and keep moving forward.
