Level up your and your team members’ goals.

Entrepreneurs plateau, but we can’t stop there or settle for 95%. We’re constantly figuring out how to get to the next gold star, the next level goal; and learn the skills needed to hit those goals.

Read Time: 5-6 minutes

By: Heather Wentler – StartingBlock Madison Entrepreneur in Residence 

I’ve been an entrepreneur for 11 years as of this month. I formally launched my first LLC in February 2011. We didn’t incorporate until March but we were well into development and momentum by then. Recently I was a guest lecturer at a UW-Madison course to tell my entrepreneurial journey. The professor introduced me to the students by saying “Heather’s been through some stuff to get her to today, but she’s always figured out how to overcome and move forward”. Ask any entrepreneur and they’ve been through some “stuff”. We all have our horror stories we try to hide, but we also learn so much by going through the process of smacking face-first into those obstacles. 

When I think about the obstacles I’ve overcome in the past 11 years, especially the last 4 years (those stories are for a different day), what I come back a lot to is my entrepreneurial community and professional service providers for how they’ve rallied around me to help me keep going. It’s not only the difficult moments that I’m facing at the moment that they’ve supported me through but also those feelings of How do I level up to be the next version of myself that best suits the needs within my venture?

We all plateau at some point in different aspects of our lives. If you’re someone who works out you’ve probably hit a point where no matter how much more you do in the gym you’re not gaining more muscle or those stupid last 5 pounds just won’t go away. When some people plateau, they feel like they’ve done enough  They’ve hit their gold star standard and are content with collecting a 95% score. Others will figure out what else they can do in addition to what they’re currently doing to get to the 100% score. They may also hire a coach or another professional to help them hit that final goal. This type of person probably has an entrepreneurial mindset.

Entrepreneurs plateau, but we can’t stop there or settle for 95%. We’re constantly figuring out how to get to the next gold star, the next level goal; and learn the skills needed to hit those goals. Unfortunately, sometimes we fizzle or spiral out at this point while overcoming the plateau – I’ve seen this happen many times. Being able to take a step back, work with someone who can help identify the next steps, and then feel confident in moving forward will get you through to the next level.

A prime example of this within StartingBlock is LÜM. If you are on the second floor of StartingBlock you will see the LÜM team buzzing around the building usually way earlier than most of us arrive and way later than most of us stay into the evening. Along with their very adorable puppers in their windows watching all of us coo at them as we walk by. The team is constantly in meetings or team huddles in the conference rooms and phone booths. I think I know the LÜM pitch just by hearing it presented in the phone booth outside my door every day 🙂 The venture recently announced they were closing for a bit to restructure. I give huge props to LÜM founder, Max Fergus, and his team for making this decision and also not viewing it as a setback. They recently announced the next version of LÜM. The ability to acknowledge the need for a pivot, overhaul the venture, and move forward with the new structure I’m sure was not a decision made lightly and also not made without external support and advisement.

I never used to believe in business coaches or putting money into a budget to receive professional development support. I figured that’s what Google was for. I felt there were enough free webinars, books, podcasts, etc. to keep a schedule full for a year so why should we pay for something? I also figured on leaning onto professional connections to help overcome challenges without incurring fees. All of these things are great, and much needed, hell, I do them now for Doyenne and promote them to others as great ways to build your customer base. 

When you see the word “Free” it also means it’s not built just for you and the specific problem your venture is currently going through. They’re going to give you a framework, story map, or guidance that works for everyone and you will still have to figure out how it works for you. From a business perspective, free pieces of advice are usually commercial snippets to try and lure you in to buy their services. They’re the freemium model for business service professionals. They work, but they still don’t get you to the 100% you’re striving for.

When you don’t invest in outside help a toxic environment can quickly take root in your venture. The mentality of “that’s why you’re here, to know the answer to this problem” creates additional problems within the venture. The blame game is a classic default of insecurity or lack of trust in yourself or your team. I’ve had countless meetings with co-founders to create space where this is the root of the problem and relationships need time and space to heal wounds that were said out of anger.  

Investing in a business coach, contractor, and professional courses have many advantages that free offerings never will. Volunteer support and coaching from people is great! But you get what you pay for in many cases – I can see you nodding your head as you read that while reflecting on a personal experience. They’re there only when it works for them, they can only help you so much before it’s not enough, and sometimes you spin out chasing free offerings and things fail because of it. 

As you continue in 2022, while holding yourself and team members accountable for smashing through goals and projections, I highly recommend considering paying for someone you and your team members need to reach 100%. It’s potentially one of the best investments you can make in yourself and your venture and will have a greater return on investments than receiving actual investment dollars in some cases. 


What to talk more about plateauing and exploring what you need to reach your 100% as your role in your venture? Or to talk about anything else related to running and working for a startup venture? Schedule an Office Hour with me.

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