Home Interviews Dan Faill of Dan Faill LLC: How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur

Dan Faill of Dan Faill LLC: How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur

by Charles Purdom
Dan Faill of Dan Faill LLC: How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur

Being a founder, entrepreneur, or a 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 Dan Faill.

Dan Faill is an accomplished storyteller and national speaker. Having worked for over a decade on college campuses, advocating for safe and positive student experiences, Dan now travels the country as a full-time speaker and consultant, engaging audiences in hard but needed conversations. Dan shares personal stories that engage and inspire others to be their authentic selves, and be brave enough to the conversations that matter.

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?

Dan Faill: And thank you for having me! I guess a lot of my journey started my senior year of college when I knew I didn’t want to work in a cubicle, but had zero ideas what I wanted to do with my life once I was forced “into the real world.” After a conversation with some student affairs staff members, I had zero clue people actually got paid to work on the non-academic side of a university. Having loved being the standard over-involved student, the path to becoming a higher education professional seemed like the next logical step. Two years and a master’s degree later, and I found myself “credentialed” to work in higher education. The sad part of following your passion is sometimes you don’t see the paycheck. The same is true in higher education, especially on the student affairs side of things; Long hours and low wages. Then I had a friend at a nearby university offer to pay me to speak to their students. After that keynote, I had a different kind of fire inside me — the desire to impact others in fun and engaging ways. The rest, as they say, is history. For nearly a decade I had a side hustle as a part-time speaker, and in the summer of 2018, I decided to take the leap and become a speaker full-time.

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

Dan Faill: Well, maybe it wasn’t so much an “aha moment” but an “oh hell no moment.” I took a position working for one campus as a full-time professional, and while I loved the position and the people, there were two things that weren’t great: working in a cubicle, and my boss’ supervisory style. I really knew it was time to start looking for my next job when my boss compared my kids to their cats (long story, and no I’m not even remotely kidding). I called up a speaker’s bureau and asked if they would represent me full-time as a speaker. Within six weeks I left the comfort of full-time employment and leaped off the cliff into being an entrepreneur.

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

Dan Faill: I think I’ve always been an entrepreneur, I just didn’t know it was called that when I was a kid. I remember in elementary and middle school I used to make my mom buy the 20lb bags of Jolly Ranchers and I’d sell them to the kids in school for like 5¢. And in high school I was in one of those monthly CD-purchase clubs and would sell CDs to friends at the discounted price; but if you ordered something like five CDs you’d usually get one or two for free, so then I would get a CD or two that I wanted (sorry to everyone in HS for that haha). So yes, I think I’ve always had creative business tendencies, I just didn’t know I could’ve been using them and refining them for the last 20+ years.

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?

Dan Faill: I bounce a ton of ideas and concepts by a group of friends, some of whom are also professional speakers and coaches. However, each time I talk shop with my friend James Robilotta, I continue to be pushed to be better. Our conversations cover a plethora of topics, from life in general to fatherhood to speaking trends to my inability to beatbox. There are few people in the world I trust wholly and fully to challenge me to be better while championing me and helping me see my own potential. I’d also be remiss if I didn’t mention two people who helped me realize a little more of my potential and how I show up in the world, and that’s Jen Gottlieb and Chris Winfield of Super Connector Media.

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

Dan Faill: I approach things differently. I view failure as the pinnacle to success and help teams and organizations understand my Phases of Failure so they can create more vulnerable and authentic environments to be more productive. I also approach everything with genuine curiosity, authenticity, and humor, providing ideas and creative outside-the-box solutions for virtually any audience. Recently I was working with a coaching client who is looking to become a speaker, and we brainstormed several different keynotes and approaches to how she can market herself uniquely. I think my excitement for the new ideas matched hers, both of us lighting up while bouncing ideas around and creating a strategy for her. It’s so incredibly rewarding to help others see their own potential.

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?

Dan Faill: 

Authenticity in everything I do. The more I stopped caring about what other people thought of me, or how I showed up on social media, the freer I became (especially the social media part). For social media, I realized I was comparing my own journey to everyone else’s highlight reel, and that simply isn’t healthy. Once I gave myself permission to break through that façade, I became more honest with myself and others. With clients I’ve been told I am unapologetically authentic, always being honest and not holding back with whatever the topic at hand is.

A focus on relationships and helping without expectation of something in return. Honestly, this is a bit newer for me. For many years I operated in the “what’s in it for me” mindset, and I think my relationships (both personal and professional) suffered because of that mentality. Then I surrounded myself with people who helped me better understand servant leadership, and providing value rather than expecting it. My friend and mentor, Thom Singer, asked me to reframe my approach to be “how can I help?” and that really opened my eyes to an entirely new level of giving that feels much more fulfilling in my life.

Vulnerability meets humor. I’ve been described as a cross between Brené Brown and Dane Cook, and I kind of like that. With clients and audiences that I work with, I am very open and vulnerable with my stories, but I make sure to take them on a journey with my own sense of humor and approach to things. It’s especially helpful to model the way; if I’m asking others to be more vulnerable and authentic, but hold back on my end, then I’m a hypocrite. But if I can show others how easy it is to be vulnerable, then we’ve opened up an entirely new level of relationships with one another.

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?

Dan Faill: Wow, I absolutely love this reversal! I remember being told “You’re not ready to be a speaker yet, and there’s no way you’d leave the comfort of a full-time job. Stick with what you’re good at.” That’s the thing about people who think they have our best interest at heart — if they’ve never asked what’s in your heart then how would they ever know how to advocate and support you? I waited, I held myself back, I listened to people who really didn’t care about me, I became concerned with what people thought of me. And that defined me for far too long.

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?

Dan Faill: I have no idea how many times I’ve heard that it’s all about “work/life balance.” That is a myth — there is no such thing as balance. To be balanced implies that everything has equal weight; So for work and personal life to have perfect balance is a fallacy. It’s about effective prioritizing. We must understand that we are people with lives, and work is only a part of that life. An effective leader or supervisor understands that sometimes life is hectic, while other times there are major work projects that need our attention. Burnout occurs in the workplace when there are unrealistic expectations in place and the humanity of our employees isn’t appreciated. I heard somewhere that people don’t leave jobs because of the work, they leave because of their supervisor. But if burnout does happen, my friend, Dr. Kate Steiner is a burnout recovery coach and I’m happy to make some connections!

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

Dan Faill: This might sound like a broken record, but be more vulnerable and authentic, not authoritative. Titles give authority to someone; vulnerability will allow the group to show up and thrive. I think too often leaders feel like they must be perfect, but in that quest to show perfection they inadvertently put themselves on a pedestal. And that’s not leadership, that’s entitlement.

Can you help articulate why doing that is essential today?

Dan Faill: Think about it this way, and allow me to geek out really quick. Superheroes are a great example, especially when comparing DC to Marvel. When DC introduced Superman, literally nothing could harm him (Kryptonite was introduced five years later in order to make the stories more engaging). Marvel superheroes were inherently flawed. Spider-Man has the angst of a teenager, the Fantastic Four dealt with family drama, the X-Men were introduced as people who were born different than others. Those flaws make them more engaging because people can identify more with imperfections than with perfections. As leaders, our flaws can also make us more relatable and engaging, so rather than hiding them and pretending to be perfect, we should lean into the imperfections more.

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?

Dan Faill: On my end, I’ve seen two main issues. First is that there aren’t the correct systems in place. Maybe the reporting structure is off, maybe the way customer feedback is received isn’t effective, maybe it’s the way marketing is rolled out. Systems dictate success. However, one of the bigger areas of concern I’ve seen is staying stuck in the status quo, or only doing it the way the CEO/founder wants it done. Sometimes a great idea takes on a life on its own, so it’s our responsibility to guide it, but not stifle it. If you hire someone on your team, that’s an exercise in trust. Will you trust your team to do their work, or will you stay over their shoulder and keep pulling them back?

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”?

Dan Faill: For me, there is no better example of the dramatic lows this than the last 12(ish) months. When the pandemic closed everything, I lost dozens of engagements within the span of two weeks. Needless to say, I curled into a fetal position for a little bit. And as a solopreneur things can get lonely. However as you continue the ride on the entrepreneurial rollercoaster, the highs that come along can feel breathtaking. From landing a long-term retainer for a client to getting the best testimonial from a coaching client; there are times where you are on top of the world and never want to come down. Yeah, entrepreneur life is full of unexpected ups and downs; But I’d rather be on that rollercoaster than on the merry-go-round of a regular job.

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.

Dan Faill: I’ve got a great example of a fairly recent win. I was booked by an organization to do a panel one week and workshop the next, after the panel I was contacted by the vice president and said they wanted me to work with more of their constituents for the rest of the year. As if that feeling wasn’t enough, rather than just booking one or two more engagements with them, I was able to leverage it into a retainer for the rest of the year. And I cannot be more thrilled at the chance to really dig deep and work with them to make an impact in the world!

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.

Dan Faill: Well, I kind of mentioned it before, but the feeling of watching dozens of keynotes, workshops, and consulting contracts vanish like a rabbit with a magician, well, it wasn’t a good feeling. At all. I did a little of the math and my business took a little over a 40% hit in income that year. I physically and metaphorically curled into a fetal position for quite some time.

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

Dan Faill: Thankfully I have an amazing brain trust of fellow entrepreneurs and business owners that I can be vulnerable about these feelings and figures with, which helps you feel like you’re not alone. We throw around ideas to help each other live out our motto of H.O.P.E., which means Help One Person Everyday. I also started doing some mindset work. For many years I wrote it off as woo things that don’t really help me and my personality. Now every night before I go to bed I write my daily wins — even small things that help me feel like it was an amazing day. It could be something as small as organizing some files or making a great dinner from scratch, or something large like rocking a keynote or workshop for an organization. Big or little, “win” is spelled the same way.

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

Dan Faill:  

Have your crew(s) – I say crew(s) because I’ve got a couple of different crews. My friendship crew is people I’ve known for years, and they’ve been amazing helping me keep my head and spirits up, especially over the course of the pandemic. If not for my friends I’d be a lot lonelier and probably not laugh near as much. I also have an incredible entrepreneur brain trust crew. These people have been one of the main reasons I’m doing more mindset work, I’ve leveled up what I do in speaking and coaching, and how I show up for myself. They are my champions, helping me achieve more than I gave myself permission to do.

Set boundaries – When you’re an entrepreneur, it’s incredibly easy to just work any and all the time. I’ve had to set boundaries for emails, time on Clubhouse, social media engagement. Everything needs a limit, kind of like a credit card. Because once you max out, you’re no good to anyone.

Say it with me… “No.” – It’s amazing how one of the shortest words and sentences in the English language is also one of the hardest to say. This is kind of similar to the earlier point of setting boundaries, but “no” can be oh-so freeing. You’re literally giving yourself permission to put yourself first. It’s easy for us as entrepreneurs to want to serve and help. I love extending the helping hand to all who need it. But there are only so many hours in the day, and apparently, it’s healthy to get a good night’s sleep too.

Sometimes you need to be WTF (Willing To Fail) – You know, I never really liked the question “what would you do if you knew you could not fail?” I feel like there’s inherent laziness built into it — if you knew you could not fail would you even try? I talk about this with my Phases of Failure (image below), which puts failure as the pinnacle of success. If we’re vulnerable, then we’re open to more ideas and ways of thinking. That openness leads to creativity, which in turn unlocks passion. Have you ever talked with someone who has an incredible idea? They light up with excitement! That passion drives them to try something new, which means they’ll learn something new. That learning might show up as a failure, which is life’s best lesson. As entrepreneurs, or CEOs, or even human beings in general — we need to be WTF more often.



Find a place to cry – Yup, I said it. Expressing your emotions is natural, and we need to give ourselves permission to experience the highs and lows. Sometimes we don’t even know we need a good cry, and then a random song or commercial comes on, and then there are waterworks. Or maybe that’s just me… But if I’m going to be the best version of myself, especially as a vulnerability and authenticity speaker and coach, then I need to let myself experience all of my emotions, even crying.

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?

Dan Faill: For me, I would define resilience as the ability to live by the lyrics of Chumbawamba’s 1997 immortal classic song Tubthumping — “I get knocked down, but I get up again. You are never gonna keep me down.” In all seriousness though, resilience is kind of like taking a road trip to a dream destination, and then hitting speed bump after speed bump, and then a detour; those obstacles are just part of the journey. Resilient people fall in love with the journey, not just the destination.

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

Dan Faill: When you grow up with the last name Faill like me, everything feels like an exercise in resiliency. Growing up in the south with divorced parents, not a lot of people talk about emotions, especially men. Most guys are taught to bottle up everything, and I was no different. I didn’t talk about my feelings much. So when I married I still struggled to open up fully. Fast forward several years, two kids, and my own divorce later; it could have been easy to just bury those emotions again, not talk about anything. But the end of that part of my life was not the end of my overall life. My mess is part of my message. I’ve grown so much and am so much more open with family, friends, colleagues, and clients. My ex-wife and I co-parent like badasses, mostly because I let go of my own ego and embraced that our kids will see two parents who love them unconditionally and still get along. I mean we still do family trips and vacations because we enjoy each other’s company, and it’s all about our kids. Resiliency shows up in many unexpected ways if you learn where to look.

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

Dan Faill: One of my favorite quotes is from John Lennon: “Everything will be ok in the end, if it’s not ok, it’s not the end.” I have a firm belief that things will work out somehow. Maybe not in my favor, but things will work themselves out. Of course, I still get stressed and freak out from time to time, but usually, I’ve got a decently calm demeanor in stressful situations, and tend to be the opposite of Chicken Little when it seems the sky is falling. What’s really helped me lately is realizing and writing my daily wins. As entrepreneurs, it’s easy to feel overwhelmed and that you’re behind in any and every task. Here’s the thing: work will always be there, and you can’t do everything. So cheer on your wins, regardless of how small they might seem to you, and look at tomorrow full of potential.

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.

Dan Faill: Think of it this way, which Winnie the Pooh character would you like to follow? Would you like a leader who embodies Eeyore, always solemn and downtrodden? Or maybe a Tigger, who is incredibly (almost naively optimistic)? Or maybe a Pooh, who approaches obstacles with curiosity and wonder, with a positive spin, and always makes time for others? A leader sets the tone for the organization. A leader’s tone will define how others do their work. A leader’s attitude is like Pooh’s honey, what we should strive for, and always hits the spot.

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?

Dan Faill: Even though it’s often misused, I have always loved Frost’s “And I, I took the [road] less traveled by, and that has made all the difference.” For me, I feel like I’ve always been a disruptor. I like doing things differently and not conforming to tradition. After all, tradition is just peer pressure from dead people. Just because something has always been done that way doesn’t make it the right way. It just means we haven’t done it differently, yet. I love to live in the land of “what if” and help others find their own potential. I enjoy taking hard conversations like failure, impostor syndrome, and vulnerability and making them fun and engaging for others. I’m happy to share stories with people and listen to their stories too. After all, our stories connect us on a more human level. And that’s the foundation upon which we can build something incredible.

How can our readers further follow you online?

Dan Faill: I’m @DanFaill on all social media platforms, and my website is www.DanFaill.com. I’m happy to connect, however!

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


Dan Faill: And thank you so much for the chance to work with you again and make an impact on others!

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