Eleanor Haglund Of Aspire360: ” Defeat and failure can be crushing”

Things will go wrong, and when they do, you need to be able to dust yourself off and try again. Defeat and failure can be crushing, but you can’t let them keep you from success. Things won’t always go your way, so being resilient can help you bounce back gracefully. Being a founder, entrepreneur, or […]

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Things will go wrong, and when they do, you need to be able to dust yourself off and try again. Defeat and failure can be crushing, but you can’t let them keep you from success. Things won’t always go your way, so being resilient can help you bounce back gracefully.

Being a founder, entrepreneur, or business owner can have many exciting and thrilling moments. But it is also punctuated with periods of doubt, slump, and anxiety. So how does one successfully and healthily ride the highs and lows of Entrepreneurship? In this series, called “How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur” we are talking to successful entrepreneurs who can share stories from their experience. I had the pleasure of interviewing Eleanor Haglund.

Eleanor Haglund is the Founder and CEO of Aspire 360, a network for entrepreneurs that provides facilitator-led, peer-to-peer community groups for founders to accelerate their professional development while running their business.

She was an inaugural member of the Innovation Scholars Program in Project Olympus and has participated in two accelerator programs (Health Wildcatters and eLab NYC). She has won awards in several startup competitions, including the Columbia Venture Challenge, McGinnis Competition, the CMU Venture Challenge, and Hack-a- Startup. She is a Carnegie Mellon (BA) and Columbia University (MBA) alum.

Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

I’m a serial entrepreneur and it’s been a long time since I could imagine myself doing anything else. I am also about to finish business school.

The first startup I ever created was a failure. I’m not going to sugarcoat it or try and hide the fact that it was a failure. But I learned so much from it. Everything I experienced about marketing, market sizing, product development, and more taught me a valuable lesson that I used to build much more successful businesses in the future.

What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

I love entrepreneurship, and especially the strong community surrounding it. Starting a venture on your own can be lonely, challenging work, and I was always lucky enough to have that educational support to help answer questions and decide what to do next.

Aspire360 was founded out of that insight. What if we could create a network for founders and provide them with the resources and community to help make better decisions around their venture?

In your opinion, were you a natural-born entrepreneur or did you develop that aptitude later on? Can you explain what you mean?

I think we all have an entrepreneurial spirit within us, it’s just having the tools and mentorship to bring it out. I was lucky enough to get involved in startup and entrepreneurship culture in my undergraduate experience, at Carnegie Mellon. Those experiences, from pitch competitions to workshops, really brought out that natural-born entrepreneurial spirit that had been there all along.

Was there somebody in your life who inspired or helped you to start your journey with your business? Can you share a story with us?

My parents both inspired me to start entrepreneurship. My mom taught me that I could do anything, and imbued me with confidence and a desire to seek out challenging situations with the belief that I would be able to think through them and learn. My dad taught me calm under pressure and how to effectively work with and manage teams. I attribute everything I have created to them.

What do you think makes your company stand out? Can you share a story?

I think the sheer amount of talent and experience we have in our mentor network is incredible. Altogether, they’ve raised millions for their ventures and other startups they’ve worked with. Our coaches have dozens of successful exits under their belt.

Being able to tap into even a fraction of those experiences is powerful for founders just beginning their journey.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Positive thinking

As I mentioned above, my first startup was not one that I exited successfully. Many people would consider that a failure, but I think it was the perfect first experience with startups. I learned so much and stayed positive the whole time, figuring out how to take each experience as a learning opportunity. Things were not perfect, to say the least, but that only meant there was so much more to learn from.


I think if you can’t be honest with others, you’re probably not being honest with yourself. To ride the highs and the lows, I rely on the people around me. During the lows, I encourage entrepreneurs to be honest with the people in your life about what’s going on in your life and don’t be ashamed or embarrassed to ask for help — remember, it’s not a sign of weakness to ask for help, it’s a sign of strength.

Celebrating the little wins

Being an entrepreneur is tough, and we often end up focusing on the long game and ignore the milestones along the way. The destination is as important as the journey, so celebrating small wins can transform the way you see growth. That one additional customer, that contract, the kind thing someone said about your business that day are all just as important as the goal that you have. Celebrating these helps even out the emotional rollercoaster.

Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

The phrase “fake it till you make it” is always thrown around, but I think that can be damaging for entrepreneurs. When you feign confidence or knowing it all, you miss out on opportunities for learning and growth. The best leaders are the ones who admit when they have no idea what they’re doing and ask for help.

Which tips would you recommend to your colleagues in your industry to help them create a work culture in which employees thrive and do not “burn out” or get overwhelmed?

Entrepreneurs are notoriously passionate, and known to keep pushing towards their vision, even when burnout happens. That’s amazing, because startups need someone who always believes in what they’re doing, but that sometimes unhealthy expectation to work can trickle down to other employees.

To prevent this, you’ve got to cultivate a deep sense of trust among your team. Trust that they’ll complete their projects, show up, and stay engaged. That means clear communication, but also the understanding that people get things done at their own time and pace. Ignore the instinct to micromanage.

What would you advise other business leaders to do in order to build trust, credibility, and Authority in their industry?

Having a strong network and peers that advocate for you is more powerful than anything you could do or say on your own. Understand that building a network takes time, but that creating deep connections will pay off.

Can you help articulate why doing that is essential today?

We’re increasingly disconnected. I think people forget how much they can learn from the lessons of others, and not just on their own. Everything from YouTube videos to reaching out via LinkedIn can turn up an unexpected mentor, lesson, or ah-ha moment. You can do it all on your own, but why not ask others for help and wisdom?

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

They think they have to do everything themselves when in reality, NO ONE is good at everything. Don’t be afraid to reach out to your network and ask for help or resources.

Ok fantastic. Thank you for those excellent insights, Let’s now shift to the main focus of our interview about How to Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur. The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. This might be intuitive, but I think it will be very useful to specifically articulate it. Can you describe to our readers why no matter how successful you are as an entrepreneur, you will always have fairly dramatic highs and lows? Particularly, can you help explain why this is different from someone with a “regular job”?

Entrepreneurs are often passionately tied to their mission. Their venture could feel like an extension of themselves. So, when they inevitably face failure on the job, it doesn’t feel like failing at work, it feels like failing as a person. The lows can feel like a direct reflection of you, and your hopes and dreams. Alternatively, the highs feel amazing because it’s so personal.

This is often different from a “regular” job, where you don’t define yourself by a company alone.

Do you feel comfortable sharing a story from your own experience about how you felt unusually high and excited as a result of your business? We would love to hear it.

It might sound counterintuitive, but lately, the joy of problem-solving has made me excited about my business. At first, nothing makes sense, but through partnerships and brainstorming, you get that ah-ha moment seemingly out of thin air.

When everything clicks, whether it’s through talking to entrepreneurs, VCs, or angels; or just working internally, it feels amazing.

Do you feel comfortable sharing a story from your own experience about how you felt unusually low, and vulnerable as a result of your business? We would love to hear it.

I think other founders can identify with this, but when I am not managing my energy well, it starts to get to me. Overdoing it with 12-hour workdays and no days off can really impact my perspective. Small things start to bother me more than they should, and it’s hard to keep that positive attitude afloat.

Based on your experience can you tell us what you did to bounce back?

A friend once told me that you can’t give from an empty cup, and I try to take that to heart when I feel close to burnout. I refocus on taking time for myself and shifting my mindset away from being “on” all the time for work. We all need that time to reset and fill our cups before going back to work.

Ok super. Here is the main question of our interview. What are your “Five Things You Need To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur”? Please share a story or an example for each.

A good support system

You need people to celebrate the highs with and commiserate the lows with too. Going at it alone means every failure rests on your back and every high is commemorated alone. A solid network to fall back on means sharing all your positives and negatives and getting valuable feedback and support.

A healthy dose of honesty

You need the humility to admit when things aren’t working, and be able to reach out to your support network for help. Many of us have a hard time admitting when things are going our way and when we need someone’s expertise to help us out. If you want to be a successful entrepreneur, you’re going to need to cultivate honesty.


Things will go wrong, and when they do, you need to be able to dust yourself off and try again. Defeat and failure can be crushing, but you can’t let them keep you from success. Things won’t always go your way, so being resilient can help you bounce back gracefully.

An outlet

As an entrepreneur, your venture can very easily become your everything. While it’s exciting to throw yourself into something wholeheartedly, you’ll want to have a life outside of it all. When all you have is work, you’ll start to equate your venture’s success with your self-worth.

Having some kind of hobby, anything from cycling to a weekly knitting circle encourages you to think outside your singular vision.


When you really believe in something, it’s easy to get tunnel vision. However, if you don’t have flexibility, there’s a good chance your vision will fail. You’ve got to be flexible, allowing for mentors, employees, and customer data to shape your vision.

If you hold on to your one true vision, even when it’s not working out, you lose out on a chance to evolve, grow, and build a better company because of it.

We are living during challenging times and resilience is critical during times like these. How would you define resilience? What do you believe are the characteristics or traits of resilient people?

Let’s start by what I don’t think resilience is. When things go wrong, resilience isn’t ignoring the failures or not letting them impact you. Resilience is getting back up again, despite the emotional impact.

I think resilient people allow themselves to feel and accept failure. They know when to ask for help, and when they might have to take an idea back to the drawing board. A resilient person feels it all and still gets back up again.

Did you have any experiences growing up that have contributed to building your resiliency? Would you mind sharing a story?

As I said, I think resiliency is the process of picking yourself up with you and getting knocked down. And part of that is not seeing getting knocked down as a failure. It’s information that tells you that something wasn’t working and you need to adjust. Something that made me resilient was that anytime I “failed” growing up, my mom would ask me the simple question “Did you try your best?” and if I could answer that question and find something to learn from the situation, then it wasn’t a failure at all.

In your opinion, do you tend to keep a positive attitude during difficult situations? What helps you to do so?

Sometimes it helps me just to acknowledge that everything is temporary. Both good and bad moods will pass, and some days will hold more struggles than others. When I accept that those attitudes are temporary, it’s easier to let go of those feelings, and let them pass. And then it opens up opportunities for growth.

Can you help articulate why a leader’s positive attitude can have a positive impact both on their clients and their team? Please share a story or example if you can.

This sends me back to middle and high school and being randomly assigned to group projects. In theory, working in a group should make the project easier, you can divide up work, playing to the strengths of each person, to create something amazing that you could have never done on your own.

But, I remember working in groups when it was a struggle the entire time. Thinking back, I often attribute those pain points to attitude. Negative and positive attitudes are contagious, and when you introduce one to a group, its impact is clear. A negative attitude will shut others down, kill productivity, and stifle innovation. A positive attitude will coax out the best ideas and strengths in others. It can make something seemingly impossible feel lighter and even fun.

Leading with positivity trickles down to the whole team, even if we’re not still in high school.

Ok. Super. We are nearly done. What is your favorite inspirational quote that motivates you to pursue greatness? Can you share a story about how it was relevant to you in your own life?

A quote that has stayed with me for a long time, is one that I heard in the movie “The Emperor’s Club.” The quote was “Great ambition and conquest without contribution are without significance. What will your contribution be? How will history remember you?”

For me, this has guided my hand. I’ve had a lot of opportunities that I could have pursued, but I evaluated each one through this lens of “Will this be an interesting challenge?” and “How will this contribute to the world and the broader community?” If I wasn’t satisfied with the answers that I gave to those questions, I couldn’t pursue the opportunity further.

How can our readers further follow you online?

Feel free to connect with me on LinkedIn (https://www.linkedin.com/in/eleanor-haglund/) if I can help you.

You can follow us on LinkedIn, Twitter, and Facebook: @Aspire360CEO

This was very inspiring. Thank you so much for the time you spent with this. We wish you continued success and good health!

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