Home Interviews Scout Sobel of Scout’s Agency: How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur

Scout Sobel of Scout’s Agency: How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur

by Charles Purdom
Scout Sobel of Scout's Agency: 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 Scout Sobel.

Scout Sobel is the Founder and CEO of Scout’s Agency, the host of SCOUT Podcast, and the co-host of Okay Sis Podcast. She specializes in amplifying female voices through podcasting and illuminating the areas where mental health and entrepreneurship intersect.


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?

Scout Sobel: I found entrepreneurship sitting at a coffee shop with a friend. I had recently dropped out of college, been hospitalized for my bipolar disorder, and was barely holding a job as a barista. I asked her, as we flipped through the pages of an indie magazine if she wanted to start a magazine with me. That moment plunged me into my entrepreneurial journey which has had many stages. My magazine ran for three issues, was sold in Barnes & Noble, and Halsey graced our third issue.

That magazine was the spark that ignited something major in me — something that I would chase until the end of time. It wasn’t until I found podcasting though that my career really settled and arrived. I started the Okay Sis podcast with my sister Mady Maio in late 2018. I recognized the power of guesting on a podcast from the reaction our community would have to our rad, female guests. They would purchase their product and follow them on Instagram. I saw the power firsthand when Mady and I started being guests on podcasts. Our downloads went up and our community grew. Thus, the power of podcasting became so apparent to me that I started Scout’s Agency in February of 2019 to get women as guests on podcasts.

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

Scout Sobel: There was never one “aha moment” that led to me starting Scout’s Agency. I believe it was a culmination of signs that pulled me along the road. I had come to witness the power of podcasting and knew I wanted to play in that arena — 1) because I loved podcasting and 2) I found it to be the most intimate, vulnerable, and human form of PR. When I started my agency, I didn’t do much thinking. I had a media kit made up that outlined three services: booking guests for podcasts, booking clients as a guest on a plethora of podcasts, and traditional PR. I started in the podcasting industry because that is where I came from with Okay Sis and emailed 1,000 podcasters to build my initial roster of 10.

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

Scout Sobel: I hear stories of entrepreneurs who were setting up lemonade stands, garage sales, paper routes as kids — anything to make a dollar. I was not that kid however when I was a freshman in high school, I had an intense urge to get a job and make my own money (which I was then denied because my parents didn’t want to drive me to work every day in addition to my school which was 30 minutes away!). I wanted to support myself at a young age. I always had this inherent knowledge that I did not fit the conventional mold. I rejected GPAs, test scores, and SATs. I knew that my inherent talents did not lie in a multiple-choice assessment. In that respect, I was mindset-wise setting myself up to find entrepreneurship in that I wanted to do things my way. Instead of attending physics class, I would skip school and go read Allen Ginsberg’s poetry at my favorite coffee shop. I felt that was a better use of my time than physics (which I had a feeling I would never need!) and so I placed my energy in areas that built me up, not drained me. This rebellious mindset in high school I believe was the entrepreneur in me building.

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?

Scout Sobel: I have had many mentors throughout the journey — some I personally know and others I have admired from afar. My father is an entrepreneur, so I always went to him (and still do go to him!) for business advice and education. He really was my sounding board in the beginning as I was trying to figure it at all out. He has sat in meetings with me and lawyers to make sure I was represented and treated fairly, he has answered all of my questions from how to do my taxes to what a PnL is, and brought me back down to reality when I get emotionally overwhelmed.

Ayn Rand really influenced my entrepreneurial spirit since I read Atlas Shrugged while I was launching my first magazine. Women like Sophia Amoruso with her book Girlboss helped show me that there was a place for female entrepreneurs.

There was someone who really set me up though to have the entrepreneurial spirit — it was a small moment, but one I will always remember. I was working as a gelato scooper and I needed to open a jar but was having difficulty. I asked my boss if he would open it. He looked at me and said, “What would you do if I wasn’t here?” to which I replied, “I would figure out how to open the jar.” From then on, I adopted that attitude — if no one else is around to help, I will figure it out myself. Which I have and I will.

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

Scout Sobel: I believe my company stands out because of the way we relate to our clients. There is an extreme amount of empathy we bring to client relations. We represent dream women because we believe in them. We want more than anything to see them succeed. With that more human, empathetic approach, we approach writers, journalists, and podcast hosts with almost a personal interest and backing of our client. My clients often say that they can trust Scout’s Agency, that we deliver, and that they know we care.

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?

Scout Sobel: 

Feeling Safe in My Emotions: As someone who has lived with bipolar disorder for 15 years, I believe that the moment I learned to feel safe in my emotions was the moment I learned how to be a successful business leader. Entrepreneurship is putting out a lot of fires — a client is upset with a podcast we booked her on, the calendar didn’t have the right link, the host was a no show — and the ability to fundamentally know that I am safe in my emotions helps me walk through that fire and show my team that they can handle challenging business moments as well.

Perseverance: The inherent fundamental law that I live with is that I will not give up. Even when the going gets rough, even when things are uncomfortable. The first year of starting Scout’s Agency, our revenue tanked right after I had brought on my first employee. I paid myself near to nothing for three months, ate into most of my savings, and created a lot of anxiety within my marriage. Giving up though? That was never an option, not even for a slight moment. On month four of low revenue, I doubled my revenue and have had record-breaking months since.

Supporting My Team: I hated working for someone else. The idea of being chained to a desk from nine to five with no flexibility to work with your biology (some days you need a nap!) or no breaks to grab an extra-long lunch with your friend that is in town really doesn’t sit well with me. I inspire my team to manage their own workload as long as they are available during meetings that are on the calendar. I want them to feel freedom over their lives. I oftentimes get a Slack message that says, “Slept terribly last night! Going to take a nap, I’ll let you know when I am back online.” I would rather my team take a nap than work through miserably with brain fog just to hit the quota of making it to 5:00 pm. This empowers them to feel good physically, be inspired by the power they have over their own lives, and creates a work culture that is balanced and fulfilling.

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?

Scout Sobel: A story about the worse advice I ever followed isn’t coming to mind, but an entire mindset is. When I started my business, I lived within a scarcity mindset around money. This idea that your revenue can be taken from you at any point is a fear-based one that multiplies fear. I am realistic, of course, but I have such a different view around how money works, the energetics of money, and how truly available it is for us all. Just because the agency down the street signed five more clients does not mean that there are five fewer clients for me to serve. It means that those were not my dream clients and the ones I am meant to serve, I will. Through this idea, money flows pretty effortlessly in my business. The worst mindset I ever prescribed was that money is a scarce commodity that I need to hold onto and suffocate in order to thrive.

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?

Scout Sobel: I would recommend employing the “self-employed mindset” with your employees. I give my team a lot of flexibility when it comes to the official hours they are on the clock. They take time off in the middle of the day to go to therapy, have lunch with a friend, work out, or take a nap. When your employees feel as if they have control over their daily lives without their boss breathing down their neck to completely control their nine-to-five window, they work through a refreshed lens of inspiration.

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

Scout Sobel: I would advise them to first focus on the results of their company. Results always speak for themselves and will provide the credibility marker for them to become authorities in their industry. Before you talk about the thing, make sure you have done it dozens if not hundreds of times so that you can back up your words.

Can you help articulate why doing that is essential today?

Scout Sobel: One of the main pain points prospective clients come to me with is that they worked with another PR agency and it wasn’t a favorable experience. Yes, there are a lot of people offering the same service but if you can stand out with concrete results with a touch of empathy (business is done between one human and another!) I believe you will set yourself up to not only be trusted but be respected.

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?

Scout Sobel: The most common mistake I see CEOs & founders make when they start a business is hiring out immediately for the small things. Of course, this depends on the scope of the business — if you have millions of dollars in funding and need to hire a time immediately, different story — but I do believe that there is much merit in the CEO & founder doing the daily more minute tasks. If the CEO & founder has done every job in the company from the ground up, they have a better perspective on how to lead and how to manage.

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”?

Scout Sobel: I fit so well with entrepreneurship because I live with bipolar disorder, so the ups and downs of my life match the rhythms of entrepreneurship so beautifully. As an entrepreneur, you experience dramatic highs and lows because it all stems from and falls on YOU. When something goes wrong, it’s your reputation, your advice, and your presence needed to put the fire out. When something goes right, you see the fruits of your direct labor and past willingness to walk through the fires. The highs are high and the lows are low because each decision and situation that happens in your business is directly and intrinsically tied to you, your dreams, and your future.

In contrast, many times in having a regular job those fires and celebrations aren’t sitting on your shoulders 100%. You don’t see the direct consequences of every little thing happening in the company. You sit more focused on your job responsibilities than a large orchestrated big picture. You also get to clock out! There is no such thing as clocking out when you are an entrepreneur which heightens emotions.

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.

Scout Sobel: Ah, the mania of entrepreneurship! YES. When I signed Catt Sadler. She was my first really well-known client that lived in the public eye. I saw her at a coffee shop in LA and emailed her right away letting her know I liked her outfit but didn’t want to disturb her. She signed with me a few days later. I popped champagne and screamed around my office. It was an encouraging high because if someone like Catt Sadler could trust me, I could definitely trust myself.

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.

Scout Sobel: I hired my first employee — which is a huge deal and a lot of pressure — and then half of my roster dropped coincidently due to random factors. I had also just signed a lease for an office and so my overhead had nearly doubled. For three months, I sat in anxiety unable to pay myself. Individual financial stress is such a hard burden to bear, but financial stress when it comes to your employee’s salary and livelihood takes on a different level. I wasn’t honest about the finances with my husband which led to anxiety and turmoil in my marriage. I was in denial about the revenue being so low. It was a difficult place to be in.

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

Scout Sobel: I first had to get very honest with myself and with my husband about the state of our finances at the time. Once I got honest with myself, I took a look at my mindset — something that I was inspired to do by the mastermind I was a member of. I realized that I was entering sales calls with anxiety, fear, and desperation since I felt as if I needed to make not just one sale, but a couple. The minute I shifted from a scarcity mindset to an abundant mindset and trusted that all of this was happening for me and not to me, clients started signing with me. I also implemented three-to-six-month contracts with all new incoming clients so that I could better plan my months. At the time of low revenue, my clients were on month-to-month contracts which made it nearly impossible to budget the future of my company.

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.

Scout Sobel: 

Trust that you can handle your emotions: When things get really overwhelming, for example when an article came out about a client that was riddled with grammatical and factual errors on a major news site, I had to trust that I could move through the immediate panic to handle the situation. When you trust that you can handle your emotions, you release the additional layer of getting anxious about your anxiety. You don’t add fuel to the fire but rather figure out how to put out the fire you already have burned.

Ground yourself daily: We can all agree we want to minimize the low lows but balancing the high highs is also very important. When something good happens in my agency, I can enter into a bit of mania which results in burnout. Feel the wins, celebrate them! But do not get too carried away. In order to practice balance, I ground myself every day in a number of ways: walking outside without my phone barefoot on the grass, meditating, breathing, journaling, or praying.

Believe in yourself: As the steerer of the ship, you have to have confidence in yourself. When I started my agency, people told me I didn’t have time for it or that I was crazy for leaving a stable salary. I believed in myself which pushed me forward into execution. When things get low, hang on to that belief. You have to see the bigger picture when things aren’t going as planned — and that bigger picture is held up by your belief in yourself.

Take physical care of yourself: As entrepreneurs, it is easy for us to overwork ourselves into major overtime — nights, weekends, early mornings. That works if you’re riding the high, but it can also cause you extreme burnout and can significantly exaggerate the lows when they do come. For me, I get 8+ hours of sleep no matter what. I don’t look at my phone until 8:30 am in morning. I move my body every day. I eat clean, nourishing, and healthy foods. I take a 30-minute lunch outside where I don’t touch my phone or computer. I spend alone time doing things that have nothing to do with my business — reading, pulling cards, going for a walk. Prioritizing rest time is huge.

Move through fear: To successfully ride the high highs and the low lows of entrepreneurship, you have to have the ability to move through fear. It will pop up constantly — What do people think of me? Is this the right move? What if I lose it all? Am I being too loud here? All fear does is strip and rob you from your future and present dreams. Fear visits in the lows and the highs. For example, when a client signed a contract for the remainder of 2020, I was terrified. It was the longest contract I had ever signed with a client and I was worried about the responsibility of showing up. Fear comes when you’re down and fear comes when you’re up high. Act despite 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?

Scout Sobel: Resilience means that quitting or giving up is never an option. You can pivot and grow and move into different areas but giving up? Never. That phrase isn’t even in my thought dictionary. Exhibiting true resilience means that you see challenges as growth opportunities — that they are happening for you and not to you. If you can see the gift in every challenge, you will emerge with golden treasure.

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

Scout Sobel: I had my first depressive episode at the age of 14. I was formally diagnosed with bipolar disorder at the age of 20. I struggled with anxiety, hypomania, depression, catatonia, psychosis, paranoia, and suicidal ideation. I had to drop out of college, quit jobs and internships, and go through two outpatient programs. If I was going to have any sort of life, I had to develop a strong sense of resiliency. The way I started exhibiting resiliency and developing radical responsibility for my life is that I started infusing hope into my days. I didn’t do anything differently at first. I didn’t change my habits or my schedule or even my therapy sessions. I just decided to infuse hope into each of my days and see what happened. Slowly but surely, I grew stronger and the hope turned into a faith which turned into confidence and the ability to trust myself.

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

Scout Sobel: I don’t know if a positive attitude is the perfect terminology for what I exhibit during difficult situations. I believe I exhibit a growth-mindset attitude that is infused with complete trust that things will work out, that they unfold as they are meant to, and that every difficult situation that comes my way is strengthening me for a better future.

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.

Scout Sobel: If the leader exhibits a strong attitude, they can guide their team and their clients to resolution. Not only will they guide them through fires, but they will also inspire them with confidence that they can and will get through difficult situations.

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?

Scout Sobel: I was listening to Matthew McConaughey on a podcast and he told the story of his first talk show appearance. He was nervous and the host came to check on him in the green room. Matthew asked the host if he had any advice. The host said that everyone that does well on the show has the same mentality — they all want to be there. A lightbulb went off in my head. I molded that concept to my own life and came up with the quote I live my life by — “I want to be here.” It evokes two things in me. 1) That I want to live this life in its entirety, without conditional requests. 2) I chose all of this. Every situation I put myself in I chose and if I chose it, that means I want to be there.

How can our readers further follow you online?

Scout Sobel: You can find me on Instagram @scoutsobel (www.instagram.com/scoutsobel)! 

In the link in my bio, you will find links to my Clubhouse room which I host every Tuesday at 4:00 pm PST with another female entrepreneur around the emotional rollercoaster of entrepreneurship, you will find links to both of my podcasts (SCOUT Podcast and Okay Sis Podcast), you will find how to apply to work with Scout’s Agency, how to sign up for my Sunday newsletter to start your week off with a clear, intentional, and grounded mindset & lots of other mental health goodness.

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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