Brian Bar of Victory Lap: “Get your finances straight”

Get your finances straight. To be a successful entrepreneur, you must have a good understanding of your finances and have the cash flow and funds in place to withstand the highs and lows of the journey. Not every decision is to do or die, but it’s important to know where your finances stand so you […]

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Get your finances straight. To be a successful entrepreneur, you must have a good understanding of your finances and have the cash flow and funds in place to withstand the highs and lows of the journey. Not every decision is to do or die, but it’s important to know where your finances stand so you can have the clarity around the timeline you’re working with and can make the right decisions that not only keep the company going but position it to thrive in the years ahead.


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 Brian Bar.

Brian is the Founder and CEO of Victory Lap, a leading sales education company based in Chicago, IL. He oversees the design and implementation of all the company’s training engagements including their Sales Bootcamps, University Partnerships, and Corporate Education engagements. Brian is also a Guest Lecturer at Northwestern Kellogg School of Management on the topic of B2B Sales. Prior to Victory Lap, Brian served as the Vice President of Sales at ThinkCERCA, a fast-growing Education Technology company, and Head of Sales Onboarding at Groupon, where Brian created and led the onboarding department for the company. He lives with his wife and 3 young kids in Evanston, IL.


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

Founded in 2016, Victory Lap is an intensive sales boot camp that bridges the gap between sales professionals and top companies through aligning education with opportunity. Leveraging world-class content, industry insights, & scientific research, Victory Lap empowers students regardless of experience, to have the knowledge, skills, and confidence to reach their potential and launch a successful, life-changing career. Since 2016, Victory Lap has helped 950+ alumni accelerate their career in sales and 225+ companies, from Series A to Fortune 500, have hired Victory Lap graduates.

Prior to Victory Lap, I was the former Vice President of Sales at ThinkCERCA and the creator of Groupon’s sales onboarding department where I managed 500+ new hires. It was during my time building, growing, and leading sales teams where I saw first-hand how people from all different backgrounds — extroverts, introverts, people with an Ivy League degree, people with no degree — all have an equal chance at success. This is one of the things that really led me to want to build a Sales Education company that provides aspiring professionals with a world-class education and career opportunities, as well as give companies access to the most prepared and in-demand sales talent pool on the market. Only 4% of colleges teach sales, yet it’s reported that over 50% of college graduates end up in a sales role. This gap is astounding — and as someone who has spent a good part of their career leading sales professionals, I lived first-hand the problems associated with this. Victory Lap was started with the belief in human potential. We’re also passionate about the fact that sales are a noble career path that can lead to personal and professional success and solve many workplace inequalities that exist today.

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

I don’t believe I was a natural-born entrepreneur but rather developed into one later in life when I first started my career. One reason for this is that I haven’t always had a high tolerance for risk and failure, which is often a common denominator in a lot of entrepreneurs. Growing up, watching my family struggle economically, I tended to choose the safer path from a career and business perspective. I was first an intrapreneur within two organizations I worked at after college when I began to develop this aptitude. At both companies, I built and led key internal initiatives that directly impacted the bottom line. This was a turning point for me, and it was after these experiences when I was really able to evolve from an intrapreneur into the entrepreneur that I am today with Victory Lap.

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?

Hands down, my wife is the one person who inspired and helped me the most on my journey to starting Victory Lap. For one, she’s very successful in her career, which gave us the flexibility for one of us to take the risk and start something on our own. And when I first considered jumping into this, she was also 6 months pregnant with our first child. So needless to say it was an interesting time to start a company. But most importantly, she’s always supported me and the business throughout it all and I wouldn’t be here today, as CEO and Founder of a leading Sales Education company, without her.

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

What makes Victory Lap stand out is how effective and efficient we’ve made our educational model to the point where individuals from all backgrounds and experience levels can go from education to employment in just a matter of weeks. One story that really highlights this is an individual that went through our program a few years ago. He was seven years into med school at this point in his life, not getting the residency he wanted and realizing quickly that medicine might not be the career path he wanted to pursue after all. After just two weeks with Victory Lap, he pulled me aside and told me these last 14 days had been more impactful for him than any of his last seven years in med school. In this short period of time, we were able to not only provide him with the right skills he needed to succeed but also give him the confidence and assurance to know that sales were the right career path for him. In two weeks! This is the role education should play in an individual’s life and I think we need to be thinking about how we can be more efficient with (which lowers student costs) and doesn’t sacrifice outcomes. I’m proud that we were able to simplify the transition from education to employment for this Victory Lap graduate and 1,000+ other individuals over the last four years.

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?

  1. Belief in others. A business leader’s job is to maximize employees’ outputs to produce results, and this starts with believing in each and every individual on your team so they can reach their full potential.
  2. Ability to sell. Great leaders and great CEOs are also great teachers and educators. Which in turn makes them great at selling. Whether it be internal or external, CEOs need to be brought in and sell ideas, change, or help land large deals. Fortunately, this strength has allowed the company to excel.
  3. Keen focus on integrative thinking. There’s no manual that tells you how to run a company and scale it. There’s lots of advice though and it’s being able to take opposing views and extract the best ideas and plans that have allowed us to really sustain as a business and do so without taking any funding to date.Logic is an underutilized skill that is often downplayed within companies.

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?

“Nail a niche.” We spent the first two years at Victory Lap focusing only on one core offering (boot camp) and we were not as opportunistic within other market opportunities that have now taken shape since COVID-19. Had we diversified earlier we would be a little further along in our long-term outlook.

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?

  • Check-in with employees 1:1. Good leaders have figured out that 1:1 coaching has a much higher multiple of return vs. group coaching, and by doing this, you will find ways to empower, add value, and coach & develop your team on an individual level. Each 1:1 time also creates more opportunities to build a culture focused on appreciation where employees can thrive instead of burning out.
  • Avoid always talking business and get to know employees personally. By doing this, you’re not only building a culture where employees feel more comfortable, but you’re also able to better understand what motivates and inspires team members on a more personal level and can cater towards this throughout their career progression.
  • Provide your employees time to breathe and recharge. This is more important than ever before with the remote work environment we’ve been living in this last year. Employees need scheduled time away from their computer screen, away from Zoom, and away from their home office in order to recharge and continue to bring their best in a remote environment. Encourage this and do it yourself to set the precedent.

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

In today’s digital world, anyone can dub themselves an “expert” in a particular field or subject, but not everyone has the past or present-day track record to back up their claims. Results, on the other hand, can’t be questioned and often speak the loudest when it comes to building authority in any industry. Business leaders should always focus on efficacy with whatever their end result is for their customer base and trust and credibility will follow.

Can you help articulate why doing that is essential today?

  • Social platforms (Twitter and LinkedIn) are being overrun with amateur Monday morning quarterbacks that offer little depth to complex problems. True leaders and experts should look at this as an opportunity to speak up and out on key themes impacting their space.

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?

  • Training and development are reactive, not proactive. Often, we see employers wait until a problem is too large before they put some sort of training or development together, but by this point, it’s too late. Whether it’s on a company or individual level, it’s important to focus on the problem when it’s small enough to fix.
  • Focus on the wrong things, a lot of which does not revolve around acquiring customers and/or making them happy, keys to any successful business. If more businesses got their talent, sales, and customer success playbooks right then they will avoid a lot of issues.

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”?

The life of an entrepreneur is never an easy one and isn’t for everyone. Sure, there are definitely times when you feel the highest of highs — when you make your first hire, land a big client, find success in the face of a challenge or raise capital just to name a few. But these also are often accompanied by the lowest of lows and the emotional rollercoaster often seems never-ending. As an entrepreneur, you don’t work a typical 9 to 5 and you can’t just shut down your mind when your laptop closes. Your company is essentially your child — you think about it first thing in the morning, throughout the night, and every moment in between. And if you are doing your job as a leader right, you think about each and every one of your employees before you go to sleep at night. Because of this, you always have the feeling that someone is getting the short end of the stick either personally or professionally. The best way I can describe it is this: Working in a regular job setting feels like a lazy river compared to working at a startup where you feel like you’re riding in the front row of the largest roller coaster at Six Flags Great America.

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.

In January this year, we shared that Victory Lap raised 25mm dollars in capital to continue to drive the growth and expansion of the business. This was the first time we’ve fundraised and the first time we’ve had the chance to announce such big news to our customers, students, alumni, and supporters. It was definitely a recent high and a rare opportunity for me to stop, reflect on everything we’ve accomplished over the last few years, feel proud and give myself a pat on the back.

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.

As with many other leaders, March 2020 was a tough month that brought on many lows as uncertainty loomed. This was especially true for Victory Lap as at the time we were primarily an in-person boot camp so when the world shut down, so did in-person classes. We had to re-think our business model and figure out a way for the company to come back even better and stronger than it was pre-pandemic. As such, it was a difficult time that required a lot of difficult decisions and sacrifices in order to keep Victory Lap afloat.

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

The number one thing we had to do was focus on how we could financially extend our timeline as a company in order to survive. I spent a lot of time during the first few months of the pandemic connecting and seeking advice from mentors, advisors, and experts in the space. I wanted to get a pulse on where they anticipated things would be so I could craft a plan and better understand how Victory Lap could pivot and be in the best possible position to make it through better and stronger than ever. We extended the financial timeline by several months and made a pivot in August 2020 that has since proved to be very successful. Sitting here a year later though, it was difficult to imagine this would be possible.

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.

  1. Plan, prepare, repeat. Resilience is born out of preparation and successful leaders, especially entrepreneurs, know just how imperative this is when it comes to solving the problem at hand, keeping your mindset positive, and planning for the future even if things seem uncertain.
  2. Always come back to the impact you’re making on the customer. This is especially true in low times. Why did you start your company in the first place? What were you hoping to solve? Reaffirm the belief that your company exists for a reason. There are a lot more individuals out there that need this and could benefit from your services. It’s not about you, it’s about them — an important reminder to always come back to whenever you’re facing challenges or lows.
  3. Get your finances straight. To be a successful entrepreneur, you must have a good understanding of your finances and have the cash flow and funds in place to withstand the highs and lows of the journey. Not every decision is to do or die, but it’s important to know where your finances stand so you can have the clarity around the timeline you’re working with and can make the right decisions that not only keep the company going but position it to thrive in the years ahead.
  4. Take a break. And I mean really take a break. Shut your brain off and spend time doing non-work-related things you love. Spend time with your family, play sports, do whatever it is that will bring you joy at the moment. Successful entrepreneurs have to be 100% ON when on the job so it’s important to similarly build time into your schedule where you can also be 100% OFF.
  5. Surround yourself with great people who can do key things a lot better than you can. In startups, there’s no room for B-players. With that said, you have to stay hyper-focused and hyper-aware of the type of people you are hiring so that you’re always surrounding yourself with great people. These individuals will not only make a positive impact on the business but they will also make riding the highs and lows an easier and more enjoyable experience. And when a B-player exists, it’s best to move on for the best of both parties as quickly as possible.

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?

Resilience is not a personality characteristic but rather a series of behaviors, thoughts, and actions that can be learned and developed over time. Planning and preparation are key here as I mentioned. There’s a discipline to develop to leave the emotions out of it. Challenging times call for really difficult decisions with often the two choices being bad and worse. Too much emotion involved can have disastrous effects on your decision-making process.

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

I’m the middle of 5 children (two older brothers and two little sisters) with a very supportive immediate and extended family. But we also didn’t have a lot of money growing up so seeing my parents raise 5 kids despite that taught me a lot. It also meant that if we wanted something, we had to get it. I wanted to attend high school in Chicago about 90 minutes away and my parents supported that but I made a lot of sacrifices to do this as well. Same with college. I had to pay for that and worked three jobs through school in order to do this. It was through these experiences where I built the resiliency muscle quite a bit.

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

I have an amazing wife, friends, family, 3 beautiful children, and a dog that loves me whether I had the best day of work or the worst day. It’s this perspective that no matter how difficult the situation, I ask myself the same question before bed every night. How did I get this lucky? And it’s like magic because I wake up pretty darn happy.

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.

A leader’s positive attitude about change and the direction it will take the team and our customers are critical. We made a big business model pivot going from tuition-free to tuition-paid boot camp yet it’s having and will have a much greater impact on our students. At the surface level, this isn’t evident so the leader’s attitude and communication methods are key.

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?

“Men and women have fought wars, we can do this.”

At the end of the day, people are dealing with a lot more difficult circumstances and situations than I am and it’s a reminder to be grateful for the highs and lows that make up my story. Most people would envy it compared to what they have to deal with and it’s this perspective that gives me a deep responsibility to make the most of what I’m doing.

How can our readers further follow you online?

You can connect with me on LinkedIn or learn more about Victory Lap here.

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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