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What makes a Successful Entrepreneur?

5 things I believe every entrepreneur needs to succeed


My parting advice to you as I exit the role of StartingBlock’s Entrepreneur in Residence

Read Time: ~9-10 minutes

By: Heather Wentler – StartingBlock Madison Entrepreneur in Residence

What makes a successful entrepreneur?

This question is highlighted almost daily in publications and media outlets. These lists usually have bias, marketing angles, or clickbait within them. We all have unconscious biases, but here is a list of my Top 5 things that I believe make a successful entrepreneur based on my 13 years of experience being an entrepreneur, working with entrepreneurs, and being part of the greater Wisconsin (and national) entrepreneurial ecosystem.


1. Personal/Professional Network

Have you heard of the term Nepo Baby? It means a child of an actor, musician, producer or other industry insiders who has likely benefited from their parents’ fame or connections while launching their own career. A great example of this is Miley Cyrus. While Miley has many talents on her own (Her new anthem Flowers is on repeat for me lately), her Dad’s Achy Breaky Heart, godmother Dolly Parton, and name recognition in public helped open doors that wouldn’t be accessible or way harder to get to than someone who doesn’t have family or close friends connections.


We see this in entrepreneurship as well. Many of the names we think of as famous entrepreneurs have family ties to connections and wealth. If you haven’t read the book Brotopia by Emily Chang, it’s a great overview of who and how Silicon Valley became the way it is today. Spoiler alert, it all goes back to connections and money (and gender helps or hurts you too).


As I’ve mentioned many times in past articles, I came into entrepreneurship from being a teacher. My network was built and cultivated around those within the education field, education research and development, and family members of my students. Stepping into entrepreneurship felt like being a yellow duck in a room full of crows. I didn’t speak the language, I didn’t look the same as everyone else, and I didn’t have the family or educational background to make connections.


2. What You Physically Look Like Can Help Or Hurt You

Another check box I can never fill is “white male”. So many of our white male counterparts get deemed successful before showing success just because of their appearance. Many, many of them recognize this and do their best to support all of us “others” as we build our ventures and connections, but all too often, I still (yes, even in 2023) hear decision-makers say things like “He reminded me of myself when I was his age” or “Miss/Ma’am, Who is actually running this company and can I talk with them instead?”, or the biggest red flag when I hear it, “He’s a great guy” because there’s usually backstory they’re trying to cover up by saying that phrase. These biases are what continue to create vast gaps in who gets invited into rooms for meetings and access to resources and capital for their venture.


Fun Fact: Did you know that in 2021 only 2% of all VC Dollars ($333 Billion total) in the US went to ventures led by those identifying as “women”? And only 0.8% of those women were women of color.


This starts with those first impressions we (sometimes unknowingly) leave on others while trying to grow our network.


To use a phrase my co-founder Amy used to say all the time, “a white bro wearing a hoodie, skinny jeans, sandals, and coded something in their dorm room” is still taken more seriously and can get what needs faster than anyone else. Meanwhile, the rest of us are usually looking for a soft introduction to new connections and worrying about the following before entering the meeting or event:

  1. Can I wear pants of a certain material, or should I be in a skirt/dress? (I have been told at meetings, “Usually, we ask people not to wear jeans while meeting with us” after I show up in jeans)

  2. Are heels of any shoe type appropriate, or will they make me too tall, making others feel uncomfortable?

  3. Should I wear a blazer/jacket over my top? Is my top too revealing? Does it have adequate space for a name tag on my upper left chest region without encouraging people to look at my breasts? Will the name tag be a sticker, pin, or magnet, and will it potentially ruin the material?

  4. What makeup, accessories, and hairstyle will bring attention but not the “wrong kind” of attention or too much attention to me?

  5. Does my appearance meet what is traditionally thought of as how my race/ethnicity, religion, and/or gender/s identity look in a professional setting?

  6. (If recently transitioned gender identities or dressing in different styles) Is this going to cause a distraction instead of people seeing my authentic self?

  7. If the thing starts at “x-time” when do I need to leave, so I’m there a little ahead of schedule, but not too much, to ensure I’m not late?

  8. (And the continued newest concern) If I wear my mask will people still be able to recognize me, or will I come across as unapproachable or “that type of person” and I should just risk my chances at catching something in order to fit in?

Can you get a small idea of why women, BIPOC, and LGBTQIA+ folks continue to prefer virtual over in-person events where we’ll be in the vast minority in the room? That is on top of all of the other responsibilities we tend to have during our days where showing up in-person takes twice, if not three times, as long as a virtual interaction.


Part of identifying the gap between race/ethnicity and gender/s for successful entrepreneurs is calling out and doing better at identifying when we’re doing this ourselves. If you think of any judgmental thoughts based on someone’s appearance, it’s time to do some self-reflection and journaling as to why you have those feelings and thoughts. That will probably help you do better the next time you’re in a similar situation and break down the bias to help people feel more comfortable in the same setting as you and that you’re someone they can come to for support in the future. Also, if you’ve caused harm with your judgmental thoughts/actions/words make sure you apologize and make reparations where appropriate with the individual.


3. Accelerator Programs Don’t Equal Guaranteed Success

This point is very controversial. And I acknowledge this while also running two accelerator-type programs and partnering with many other companies that run accelerator programs. Over my 11 years within Doyenne, I have worked with hundreds of entrepreneurs who have gone through an accelerator program (sometimes multiple programs) and about the same number of people who have never even thought of going through an accelerator program. Both of these options can still lead you to be a successful entrepreneur.


My suggestion is, if you’re thinking about going through an accelerator program consider the following:

  1. Why do you want to do so?

  2. Are you looking for connections within your industry? Investors?

  3. Are you looking for business support such as Strategic planning? Business Model identification? Growth Planning?

  4. All of these will help you narrow down which accelerator program(s) you should be applying for

  5. What stage is your company in right now and how will the accelerator program move you into the next phase of growth/success?

Suppose you can’t identify why going through an accelerator would benefit you and your venture. In that case, even if you’re accepted into the program, it will probably feel like a waste of time. You’ll be going through the motions of the program while also feeling like it’s a burden on you, your time capacity, and your outcomes.


4. Mentors & Coaches

I don’t know of a single successful entrepreneur who doesn’t have mentors and/or coaches to support them and their venture. Operating within a silo does not create lasting success or growth.


When we only rely on our own thoughts and planning without talking with others who are not part of the day-to-day of the venture we limit potential possibilities, identify gaps in venture strategy, and also only go for the opportunities that are presented in our faces. Coaches and mentors don’t have only to be those we pay for services. Your board of directors or advisors are great for this, and a big way of how they should be leveraged and used. Target Market friends or colleagues are also great for this. Strangers can be great mentors for helping flush out ideas or product development because they’re fresh eyes.

Having mentors and coaches also provides a space for you to be vulnerable in a way you can’t sometimes be with anyone else as to what’s going on within your venture. When it hasn’t been your day, week, month, or year they’re there for you. They understand how to bring you back to the big picture, analyze as an outsider why certain things went the way they did, and provide support.


5. Know Your Skills, Talents and Limits… AND Trust Them!

When you’re first starting your venture, you do it all. Quite literally, you’re the leadership team, finance department, marketing department, sales department, and trash-taker-outer all in one. You’re doing what needs to be done to make sure your venture baby survives. You’re going through all those same things we hear parents of newborns go through – sleep deprivation, forgetting to feed yourself, feeling alone in the experience even if you have a partner(s) to support you, wondering if it will be like this forever, and just as things start moving towards a new normal and a routine is in place it all gets shot to hell and you pivot into a new routine and schedule based on the baby’s needs.


As you begin to have more revenues, partners, staff – basically any resources outside of yourself in general – you can start to hone in focusing your time back into the areas of your skills and talents. This takes time to get to. A question to ask yourself is how long can I sustain the chaos? Because once you know your limit, then you can set goals around making sure you don’t burn out because of the chaos.


As the venture grows, your skills and talents will grow too. You’ll feel more confident in making what you may have once considered risky decisions and also be more able to ask others for support or push back when things you’re not responsible for any longer get handed back to you. Don’t forget to listen to others when they give you advice and feedback. You can say no to it, but you should always evaluate it first as they’re probably seeing something you cannot.

I talk with many entrepreneurs who even though they now perform the role of CEO find themselves wanting to go back to doing the nitty-gritty tasks of the venture that got them started. Why? Because they feel comfortable there. They know how to do those tasks well, and it calms their anxieties around where they feel uncomfortable and know they should be putting in their time and energy. Reverting back is detrimental to the venture and usually can also signal that something isn’t going well within the culture of the venture.

Light up desk sign says "You Got This."

We learn and grow from being uncomfortable. Every one of my 5 items listed above will challenge you to feel uncomfortable in some way. Lean into it. Reflect on why you’re feeling that way, and what steps you can take to feel confident within those experiences.


What’s the key to being a successful entrepreneur? You. Understanding yourself, how your past reflects your future, and showing up as your authentic, perfectly imperfect self will make you successful. You are the one who defines “success” for yourself and your venture, remembering that makes anything achievable.


I hope you’ve enjoyed my parting advice to you as I exit the role of StartingBlock Madison’s Entrepreneur in Residence. I’ve loved writing these for you each month and hope that – no matter your professional identity – you’ve been able to find nuggets to relate with and take with you throughout your lived experiences. Doyenne and I will still be partners of StartingBlock and you’re always welcome to reach out via email to talk and support each other’s success.


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