Kari Ginsburg's Unconventional Coaching Method for Entreprenistas

Please share a brief introduction about yourself and your business:

Hey there glitterbombs.  I'm Kari, and I’m an unconventional executive coach and co-conspirator for misfit women and femme professionals who want to catapult from lonely to legendary.  Uproar Coaching (that's my company!) offers several coaching formats that can be tailored to your schedule and the level of support you’re looking for, in addition to custom workshops and bespoke consulting services.  

I’m an ICF Certified Executive & Life Coach who supports you to not only be yourself and own your inner misfit, but to unleash that power to achieve greater things as a full human - profession, personal, and everything in-between.

After we’re done, you’ll be having way more fun, you’ll finally tell your imposter inner voice to STFU, you’ll let go of perfectionism, and you’ll say HELL YES to the things that feel values-aligned

Who are your customers?

I created Uproar Coaching to work with experienced women and femmes who are really f'ing good at what they do. You have a variety of accomplishments, experience, and skills, but you’re facing challenges that lead to feeling dissatisfied, unfulfilled, and — honestly— lonely.

Since opening Uproar in 2020, I’ve coached over 250 people, including political appointees, beauty industry executives, sustainable architects, academics, leaders across levels, small business owners, stay-at-home parents and artists. 

Their backgrounds are varied, but they all have one very important thing in common: they're different.  They're the misfits and the outliers and the rule-breakers and the legacy-makers.  They're nothing short of badass.

I love my work.  I love my clients.  Supporting them is a huge privilege that I don't take for granted.

What was your background prior to starting your own business?

It's been varied, that's for sure!  I taught American Literature and Drama at a small high school, I was a wedding planner, I was leader in federal government for 13 years before I was recruited away to lead internal HR-technology change management at a Fortune 500 company, a professional actor (FUN FACT!  This is how I met TEL's own Stephanie Cartin, when we were both theater kids).  I also volunteer with local animal rescues and I sit on the board of a performing arts non-profit.

What made you take the leap to start your own business?

Like so many entrepreneurs and small business owners I know: the pandemic and a toxic leader. My high-performing team was realigned under a new leader, who then actively dismantled our processes, relationships, and reputation. Then, the pandemic arrived and all of the other activities in my life halted overnight.

I realized that the 16-hour-a-day hustle for someone else was no longer in values alignment with where I wanted to spend my work time, and I was trying to protect my team by staying when the best thing I could do for them was model growth behavior and move on; to hopefully inspire them to do the same (spoiler: it did.)

I had worked too hard and was too good at my job to let one person sink my career, because that's honestly what it felt like was happening.

After one particularly brutal day, I stepped away from my at-home workspace and found my partner in the kitchen. I told him I was miserable (His response? "I know"). I told him I wanted to quit ("I know”). And I told him that I wanted my little coaching/consulting side hustle to become my only hustle ("Let me grab my laptop"). Together that night, we made immediate moves to reduce unnecessary household expenses to give me some room to breathe financially. I set up an LLC, a website, and I printed business cards over the weekend.  For three months, I worked my full-time corporate job, albeit at a reduced 10 hour workday, and then spent 4 hours a day (including Saturdays and Sundays) building my book of business. Then, I quit. And I've never looked back.‍

What is the biggest challenge you have encountered along the way so far and what have you learned from it?

In 2023 I was participating in a group coaching program that focused on sales.  I used that program for accountability to create and launch a new coaching service -- one that I was really, really excited about AND had spent a lot of time crafting into something that I was proud of.  

Now, I don't know if you've every launched a program or a product, but prevailing wisdom is that there's a long-enough lead time up to "Doors are open!" that can get people into a traditional sales funnel.  And yes, I'm intentionally using buzzy-buzzwords here, because this is how selling was introduced to me waaaaay back when I opened my business.  I wasn't invested in that type of selling, but the group coach strongly encouraged me to go through this type of launch experience.  So I ignored my "your business your rules" better judgement, and dove in.

I created 48 unique pieces of collateral and communications to be used across email and socials.  I content-batched and scheduled, and had swipe copy for referral partners... everything was racked, stacked, and ready to go.

I needed 6 people to sign up.  6 felt easy.  The enrollment period for the initial launch was for 2 weeks.  

Doors opened, my content fired as-scheduled.  I was present and engaged across communities.  And all of that energy and effort yielded ONE client.  One perfect-for-this-offer client.  I should have been celebrating that one client, but...

I had put so much into this offer and introducing it into the world that I had nothing left to protect me from the reality of what my coach called a "failed launch."  I was encouraged to serve that one client, but to shelve the offer.  

I broke.  This broke me.  I was so disappointed that I couldn't sell in this way, even though it didn't feel authentic to me.  Had I let down my business?  What if I wasn't meant to be a business woman?  After all, I wanted to be a coach so that I could support people, not so that I could make IG Reels and pitch decks.

It took a long time to climb out of the pit I dug and then wallowed in.  In those months of mourning and recovery, I came to terms with three facts:

1) I had ignored my own business instincts: while I can take the opinions and experiences of others into consideration -- I know my clients, I know my style, and I know where I want Uproar to grow.  Theirs is input, not mandate.  I've gotten much, much better at specifying what type of support or feedback I'm looking for, in order to 

ensure I'm not allowing mis-guidance.

2) I had travelled too far away from too far away from that woman who jumped into entrepreneurship: how much easier things were when I could experiment without worrying I'd break something precious.  I'm precious.  My clients are precious.  My business model?  Totally malleable.  If I forget to play and enjoy the work experience I've created for myself, not only do I suffer BUT my business doesn't thrive.  Like so many of small businesses, Uproar is special because I am special.  

3)  I had been long overdue for a break: I put too much pressure on the success of something new because I hadn't given myself the gift of time-away and reflection.  I poured everything into my business without giving myself the same nourishment.  Shame on me.  Never again.

Since that "failed launch", this program (shortwave) has become a cornerstone of my business and is one of my most unique, in-demand offers.  It was my first coaching program to have a waitlist.  I celebrate and cherish this accomplishment every day.

What accomplishment are the most proud of to date in your business?

That I'm still here, still in business.  Starting a business at the beginning of a COVID-19 and weathering the rapidly changing peri-pandemic marketplace and still going strong is an INCREDIBLE accomplishment; one that I share with a lot of folks.  The fact that we're still here and doing what we love is epic.

Do you have any recent wins from the last year that you'd like to celebrate with our community?

I was recognized as one of the Top 15 Coaches in Washington, DC for 2024, and I've finally moved beyond that essential procrastination phase and have a complete draft of my first book.

What's next for your business? What can we expect to see over the next few years?

The word of the year is MOMENTUM, and I'm absolutely picking up the pace.  Other than my standard coaching services, Uproar will be launching its first monthly group program in Spring 2025 -- more details coming very soon -- PLUS I'll be publishing my book (a girl can dream)!  I can't wait to share it with the Entreprenista community.

What is your top productivity tip?

Like so many things, the way that you think about productivity and the way that you experience productivity are unique to you.  Hacks and tips won’t work unless you understand where you’re impacted, where you’re bogged down, where you’re motivated… where YOU are ready to commit to making a change for yourself.  

Then,  get really comfortable with what’s good enough.  You can’t be everywhere and you can’t do everything.  Discover what’s enough – what’s sustainably, honestly enough– and set that boundary and hold to it.  Here’s an easy way to start doing that.  Take a look at your to-do list or calendar for next week.

What’s ONE thing you absolutely must get done.   -- this is often client or delivery related

What’s one thing you WANT to do.  -- this is often business or back-end related

What’s one thing you WOULD LIKE to do. – this is personal

Now ideally, this is three tasks per week, but I’ve found that the overachievers and high-producers pivot this to 3 tasks per day.   You can always add more, but this is a great approach to prioritizing, executing, taking a moment to process what you've accomplished, and then move forward with intention.

What is one thing you wish you had known when you started your Entreprenista journey?

To pace myself!  I was so excited to meet everyone, to be present and supportive.  Figure out your boundaries around your engagement, and stick to it.  Fellow Entreprenista and biz-bestie Janna Carlson and I meet once a week for coworking/TEL time -- it's a delight.  I may dip in or out beyond our shared time (often, I do), but having dedicated time on the calendar reduces FOMO or the anxiety of not investing enough in the community.

What is your favorite business tool or solution and why?

My newest business tool obsession is Airtable.  I'm a recent convert, and I'm spending a lot of time setting up my workspaces, creating forms and integrations (I can create Zapier actions to Dubsado, Convertkit, Thirvecart, and vice-versa), and workflows to get some back-end business stuff OUT of GoogleDrive and desktop applications and into a more pliable space.  It's cutting down on a bunch of my previous manual administrivia.

What advice do you have for aspiring Entreprenistas?

Be bold.  Don't forget who you are.  Find a collection of business friends in different industries so that you don't have to navigate business ownership alone.  Make investments in yourself (you are a luxury item, don't ever forget it).  Don't forget to drink water.

Learn more about the Entreprenista League and join today!

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