No matter what bumps in the road may come, having a clear vision for yourself and for your company is crucial. As they say, “if you don’t know where you’re going, have a vision for yourself and your company.” This is the island on the horizon that no matter how rough the sea may become, you can always find that fixed point to reorient yourself.
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 Harris Schachter.
Harris Schachter is Co-founder and Head of Marketing at Lend-Grow. His previous roles include Director of Marketing in the direct-to-consumer medical supply space, and Content Marketing Manager at Capital One, where he created the SEO acquisition channel in US Card. Harris has been a digital marketing consultant for a decade, and his digital marketing blog OptimizePrime receives over 1 million organic visitors per year.
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?
Thank you, I’m happy to share my experience with your readers. It all began for me as an undergraduate, studying psychology and helping my advisor with a research study. Going into college, I had no idea what would benefit me in terms of employment, but I knew what interested me, which was understanding why people do the things they do. This has always fascinated me and I developed an appreciation for the differences in people and I wanted to understand the why behind our different ways of thinking and motivations.
As a research assistant, it was my responsibility to administer paper-and-pencil tests for Dr. Jeanne Ryan, a really wonderful and brilliant woman. She was the Director of the Traumatic Brain Injury Center at the State University of New York, and her research involved a somewhat antiquated test to determine the severity of brain injury an individual may have, for example following a car accident. This paper test has been used since the 1950s, first being used by the army. There were 3 different versions of it, and it was administered by changing the order in which these 3 versions were given. Dr. Ryan’s research was to investigate if there were any learning effects going on between these 3 sessions. This was a test of validity; was it really testing what we think it’s testing or perhaps patients simply learning how to do the task better (and thus the results can’t be trusted).
As a research assistant with a manual stopwatch and a pencil, pouring over these sheets trying to decipher lines on them and decide what type of path was made, it occurred to me how easy this would be if it were computerized. At the time, there were no i-pads but there were a few tablet PCs on the market. I found one with the same size screen as the paper test and applied for a research grant to make the test on the computer. I ended up teaching myself Flash, replicating the test digitally using a stylus instead of a pencil, and most importantly, it automatically timed itself and scored itself. This was a huge breakthrough for me personally; realizing a need, defining the requirements, building it, and eventually testing it with my own undergraduate peers. I presented this research at a national neuropsychology conference where most of the attendees had PhDs, and I was weeks away from my bachelors. Since then, the computerization of neuropsychological testing has become commonplace. I didn’t know it at the time, but this was my first exposure to product management.
This combination of psychology, digital media, and data-driven testing leads me to marketing. At the time in 2010, digital marketing was just taking off, and I realized this was the perfect way to combine these interests. I went on to earn a Master’s in Internet Marketing and have been loving it ever since. This field is filled with wonderful people, amazing opportunities, and plenty of green pastures to learn new things every day.
What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?
I was introduced to my Co-founder Nish Krishna by another colleague and friend from Capital One. The idea for Lend-Grow which Nish started with was heavily lender-focused, helping them make better decisions when it came to pricing, profiling, and using AI platforms to help do so, with a consumer-facing marketplace where people can find loans and get connected to lenders. When I joined, my focus was to head up the growth of this marketplace to engage more borrowers, and we quickly realized from our own experiences, from working in lending and from consumer research, that there was a major problem with these marketplaces: they feature the same big banks. For a variety of reasons, people generally distrust the big banks and want access to the smaller lenders instead. Unfortunately, smaller lenders are very hard to find and usually are not discoverable unless through a personal recommendation.
While at Capital One, I saw this happen time and again with the hundreds of millions we spent every year on digital advertising; smaller lenders are simply shut out of the digital acquisition game. But if you look at overall lending power, there are less than 500 “big banks” (those with more than $2B in deposits), but over 4,000 smaller banks (those with less than $2B in deposits). Those big banks are the only ones you see online. There is an absolutely enormous set of choices for consumers but are only exposed to a small fraction of their options. This was the big “aha” moment.
Lend-Grow is a tech-enabled fintech that makes it easy to find harder-to-find lenders and instills trust in the consumer that they will find the right deal for them and not the deal that makes the institution the most money. We’re building a platform that will give people the power to search hundreds of lenders, not the same dozen you see on every site. This saves time, effort, and money, empowers consumers to “shop local” for their banking needs, and best of all, brings trust back to finance.
In your opinion, were you a natural born entrepreneur or did you develop that aptitude later on? Can you explain what you mean?
I’ve always known I was a natural-born entrepreneur, I just didn’t know how it would eventually manifest. Entrepreneurialism runs in my family, and the earliest example I’m aware of is my grandmother’s father emigrating to America from eastern Europe in the early 1900s with very little in his pocket. He started a painting company in New York City and grew it to a sizable business, employing a number of people and becoming moderately wealthy. My paternal grandfather ran his own paper products company, and my father had his own dental practice. So it was a matter of time before I followed along the same path. Early in my career, I started my own consulting company just to have a side-hustle, partly for the additional income but mostly for the exposure to different business models, markets, and audiences, not to mention a playground to test out different marketing strategies. I’ve also built, bought, and sold a number of different websites over the years. Personally, I enjoy the “building” phase of things and creating something out of nothing. The quickest turnaround was about 6 months; going from nothing to selling the business for low 5-figures. Today, I’m enjoying all the ups and downs of building a company with a huge potential to make real change in peoples’ lives.
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?
In addition to my family members and their own entrepreneurial pursuits, today my inspiration comes from my son Nolan, who turns 1 in April. In some ways, he and my company are brothers because they were born roughly at the same time. It really doesn’t bother me working long hours because I know it is all to build up my family’s lives. I’ve always heard everything changes once you have a child, but that was quite an understatement. Like anyone, my drive is to give him all the opportunities he wants to pursue in life and hopefully become an entrepreneur himself one day. If I ever get stressed out or overwhelmed I just look at a picture of him and my partner Haley.
What do you think makes your company stand out? Can you share a story?
Lend-Grow is powerful because it’s the culmination of experience, knowledge, and opportunity. My co-founder and I have spent years in key positions at big banks, and we know exactly how to build lending businesses, what consumers want, and how lenders operate. After spending years at financial institutions, consulting for many different businesses, running my own businesses (buying, building, selling websites), it feels very natural that it would all eventually come together like this. Our team of analysts, marketers, developers, and leaders are all mission-driven, and we also have an amazing team of advisors who share this challenge with us.
In addition, the problem we’re tackling is very real, and the product we’re building is highly disruptive. We not only hear this from consumers but many VCs.
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?
Great question. Character traits are the hardest to gain but even harder to change.
- First of all, you need to have confidence in your area of expertise and know when to flex your muscles. Many times people don’t realize how much of an expert they really are, and can easily underestimate their ability to affect change. Early in my career, I was put on a project to help optimize the credit card section of Capital One’s website. I was very junior at the time, but thanks to my independent experiments, knowledge of the topic, and constant testing, I was confident in my skills and wanted to bring all I could to the table. This, combined with my naïveté to corporate email candor resulted in an intense situation. After meeting with the team and delivering a 60-page audit I spent weeks developing, with very specific strategies, a junior copywriter completely butchered these recommendations and shared them with the team. Of course, at the time, she didn’t realize how precise these were and in fact, were more like instructions than recommendations. I responded to the wider project group over email, which included some very senior leaders, and simply explained that if her suggested changes were implemented, we wouldn’t see any results. Some people were impressed, yet others were offended. In fact, I later found out one leader wanted me fired. Luckily, I had some great leaders in my own corner who vouched for me, and this moment sparked a chain of events that would lead me to better opportunities to impact the business. A few years later, I became the product owner of the SEO channel, moved to the US Card team, and pushed capitalone.com’s daily active users from 9 million to 14 million.
- The next character trait that has served me well is objectivity and a focus on data. Opinions have their place and time, but to build trust and expertise in most fields, data is king. Everything can be measured, which means it can be optimized. In the world of startups, testing becomes absolutely crucial to success, and the faster throughput you have in a high-velocity testing program, the faster you’ll uncover insights to help you scale.
- Similarly, develop a love for experimentation. If it’s one thing I learned over the years, it’s that “I don’t know” is a perfectly acceptable answer. Many people think they need to have all the answers and that not knowing something should be avoided at all costs. In reality, what they should avoid is a scenario where something is not able to be known. In other words, develop ways to create valid and reliable experiments in which you can learn something practical. Even if you or your team’s hypothesis turns out to be false, you still came away from it with new information. Instead of trying to know everything, focus on prioritizing and executing experiments to make incremental progress.
- Finally, a customer- or consumer-centric approach is absolutely key. I think this was the best outcome of my undergraduate education in psychology. If you can put your own opinions to the side and put yourself in your customer’s shoes, you’ll be able to reach product-market fit, find that bulls-eye marketing message, or develop that customer service strategy that will really knock it out of the park. This customer-first approach helped me succeed in marketing by focusing on what consumers need, what they’re searching for, and what information will help move them down the funnel. Focusing on this area has helped earn millions in revenue and tens of millions of visitors.
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?
I’ve never really taken advice from anyone, whether it be good or bad. Instead, I prefer to observe people because often what they do and what they say can be two different things.
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?
It is very easy to get burnt out, but it’s even easier to be burnt out and not know it. There is an interesting phenomenon where, on the one hand, you feel an obligation to be formal (maybe “traditional”) and show up at 9 am. However, we know there are different learning and working styles, and you have to be flexible with them. For example, I am a night owl and my best work has always been between 8 pm and midnight. Unfortunately, this leaves a high potential for burning out, since I’m arriving at the office early (let’s face it, for optics) and still staying up late to get real work done. So instead, find a way to leverage the strength and habits of each individual employee as a person, so their contributions can be the most valuable possible. If someone finds passion and inspiration at 2 am, so be it. One of the great things about being an entrepreneur is prioritizing the things that work and de-prioritizing practices which don’t work, allowing more flexibility in how you operate.
I also recommend focusing on just a few things at a time, something a great leader (Yousseff Lahrech, now Head of Analytics & Technology at Nubank) once taught our entire team. If you take this “essentialism” approach, you can make greater progress overall, instead of diluting your energy over a large number of things. The book Essentialism by Greg McKeown is an excellent read on this topic.
What would you advise other business leaders to do in order to build trust, credibility, and Authority in their industry?
The best way to build credibility is to share your knowledge with anyone willing to listen. Start a blog, contribute to others, speak at conferences, and share nuggets of knowledge on Twitter or your channel of choice. Offer up advice and share your experience in your field, and don’t just regurgitate what others have said. Sharing original material is not only good for your credibility but also contributes to the advancement of your industry overall.
To build trust, don’t just share your wins, but share your losses too. Sharing those moments when things don’t go perfectly builds your authenticity and creates confidence in others that you’ll be honest about risks, challenges, and opportunities. If you develop a reputation of being a “yes person” not only do colleagues trust you less, but your immediate teammates won’t be 100% confident in you.
Can you help articulate why doing that is essential today?
Building trust, authority, and credibility is essential today because you never know what opportunities you’ll have tomorrow. As an entrepreneur, your reputation carries over into your startup. This affects everything from hiring the best team, gaining the right type of investments, and earnings visibility for your company.
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?
By far the biggest mistake made is blindly to believe you have product-market fit right off the bat, without customer input. You have to have a firm yet flexible view about what you are doing. I sometimes describe this like roasting a marshmallow: if it’s too hot (definitive/assumptive) you’ll burn it to a crisp. No one will want your product because it tastes like crap. If development is too cold (stagnant/reluctant), nothing will happen and you’ll move too slow to accomplish anything. But if you can get into that Goldilocks zone of moving with purposeful flexibility, it will turn out perfect. You need to have a firm grasp on what problem you’re trying to solve, but figure out the best way to solve it along the way. You need the ability, agility, and open-mindedness to pivot when you need to. Only data, customer feedback, and trial and error will show you the way. No one ever dreamt up the perfect product or business by themselves in a vacuum.
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 filled with highs and lows simply because everything is magnified 100x because of resources and a smaller scale. Tailwinds and headwinds are felt with much greater intensity as a startup than a large corporation, just as smaller boats are when compared to cruise ships. Imagine startups as a speed boat; fast, agile, flexible (and fun!), and large corporations are the oil tanker. A headwind against a speedboat can be so intense the boat almost comes to a complete stop, even with all engines running. The large tanker keeps moving along without flinching. In a startup, you have to wear many hats and figure things out for yourself. There isn’t someone you can punt it to or a different department to call to figure it out. It is a constant barrage of challenges to meet, obstacles to overcome, and novel problems to solve. On the flip side, a nice tailwind can significantly boost that speedboat, and yet no matter how strong it may be, won’t budge the oil tanker from the pace it’s already on. In that startup, you may hit on a growth tactic or a partnership, or nail your product, and can instantly double or triple your customers or revenue. But in that regular job, it’s just a drop in the bucket.
As an entrepreneur, you feel everything that comes your way. As an employee at a regular job, you’re insulated from almost all of this.
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.
As an early-stage startup, the best high I have felt so far was being able to quit my day job and focus on Lend-Grow 100%. The thrill and the mental clarity that came with that leap were unparalleled; I could finally concentrate on it full time and really move things faster. Within the same time period, we also succeeded in our seed round of funding, which was amazing to gain the confidence of firms like 10X Capital and in meeting with many VCs. It is now about to wrap up and it looks like we’ll meet our goal, allowing us to continue building out the team and focus on our product. For an entrepreneur, it is probably the most exciting thing to finally have that green light.
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.
The most vulnerable I have felt in this journey was a period of three months between my 9–5 and earning a paycheck from our startup. With a mortgage, a new baby, and life coming at me, it was like jumping from one ship to another with a sizable gap in between. Most people would have waited until they could be on the payroll, but this is simply one of the sacrifices you make as a co-founder. I wanted to escape my 9–5 as soon as I could, paycheck or not because my heart was no longer in it and my mind was squarely on Lend-Grow. This was a scary time because we were burning through our life savings to keep the lights on, and at the same time raising money. It was stressful and it weighed heavily on my mind and kept me up at night because I had no idea what the outcome would be.
Based on your experience can you tell us what you did to bounce back?
I knew the best way out of this jam was to keep pushing forward. I didn’t know how or when it would resolve itself, but because our initial funding round was happening at the same time, I knew it wouldn’t be long before we’d be able to at least cover the basic necessities. In the early days, co-founders always draw lower salaries than others in the company, and certainly in comparison to previous “regular jobs”. Luckily our seed round was successful and we have an excellent trajectory ahead of us.
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.
- First of all, you need a good support system, especially at home. For about a year, I was an employee at a 9–5 job while building Lend-Grow at the same time. The days and nights were very long, and I had absolutely zero free time. On top of all of this, we were blessed with our son arriving in April 2020. Luckily, my partner Haley has been along for the ride and understands the sacrifices needed to reach our goals. At the beginning of the venture we talked about what it would entail and she encouraged me to pursue it because she knew it was something I wanted to do. Over the years she’s realized it’s impossible for me to sit still, and the opportunity was calling me. She has been extremely supportive, even in my most stressful moments she is there to keep me going. In fact, I don’t think I would have been able to do this without her love and support. Being a new parent, I had, even more, to learn and tackle, not to mention doing all of this in a pandemic. It was an extremely trying time, but both she, our son, and my extended family are all there to cheer me on. I think a support system is the most important thing you can have to be successful because there are always sacrifices you have to make and situations to deal with which would otherwise be impossible.
- The next thing you need to ride the wave of entrepreneurialism is a team of amazing people who share your vision. I am truly lucky to have an amazing Co-founder, Nish, who has also quickly become my friend. Although it’s been less than 2 years, it seems like I have known him for much longer. Whether work-related or not, he always has something interesting and unique to say. We are both very analytical people but come from different backgrounds, which I appreciate. Our growing team is also key since they are all making sacrifices just like we are as Co-founders. Everyone on the team in this early of a company knows and is excited by the prospect to really build something, and we all ride the highs and lows together on the same ship.
- Although it may seem impossible as an entrepreneur, a work-life balance is absolutely essential. Otherwise, you’ll simply burn out, and your work product suffers. Personally, I’ve realized some of my best ideas come when I’m on a beach, hiking a mountain, or doing something completely unrelated to work. A great book on this topic is called “Scaling Up Excellence” which talks about the ebbs and flows of life. Even in nature, there are cyclical motions like the seasons, the sun and moon, and life itself. People are part of this natural world and the same rules apply. If you have a strenuous workout, you need recovery time for your muscles to repair themselves. The same is true for your mind. There must be periods of rest in order to recuperate and be as maximally effective as possible.
- I also find a solid routine helps a lot. This structure makes it hard to not skip what is essential and doesn’t allow you to make excuses for not working out, eating right, spending time with your family, and pursuing your personal interests and hobbies. It may sound ridiculous, but put these things down on the calendar if you have to to make sure you’re not skipping over them. Having a daily routine makes it much easier to achieve your goals little by little, without forgetting anything.
- Finally, no matter what bumps in the road may come, having a clear vision for yourself and for your company is crucial. As they say, if you don’t know where you’re going, how A vision for yourself and your company. This is the island on the horizon that no matter how rough the sea may become, you can always find that fixed point to reorient yourself.
If I may add one more to this list, it would be to stop and celebrate your wins, no matter how small they may be. It can become way too easy to overlook these times and move on to the next one, without reflection and pausing to soak in the glory of another challenge met. For an entrepreneur, the thrill of accomplishment is certainly the preferred dopamine-delivery method, but when you stop and celebrate with your team too it is a great way to build camaraderie.
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?
I believe resilience is akin to mental fortitude. There is any number of distractions today, each one of these is a ploy to steal your attention, time, or energy. I say resilience is akin to mental fortitude because it really does take a healthy state of mind and unshakeable confidence to do what needs to be done. To avoid these distractions, you must first recognize them. I think the ones to be most aware of are our food system, social media, media, Hollywood, and materialism. Unfortunately, I don’t think our society is at the point where it can help each individual realize their true potential, so it is up to you to become self-actualized. I believe resilient people have an attitude about life that’s simply uncommon, and allows them to think rationally about any challenge that comes their way. As they say, where there is a will, there is a way.
Did you have any experiences growing up that have contributed to building your resiliency? Would you mind sharing a story?
I attribute a lot of my achievements and attitudes about life to the way I was raised. Growing up, I didn’t have helicopter parents (thankfully, as this probably would have made me less successful). Instead, I was given opportunities which I could either take or leave. My father did a great job of instilling a sense of personal responsibility in me, showing me you get what you earn and nothing more than that. Everyone carves their own path in life. Nothing is handed to you, and I knew I had to work for the things I wanted in life.
In your opinion, do you tend to keep a positive attitude during difficult situations? What helps you to do so?
A positive attitude is absolutely essential, particularly in difficult situations. I also believe this is a choice, you can choose to be positive or you can choose to be negative. Someone once told me whether you have a good day or a bad one is something you decide in the few moments after waking up. It really doesn’t matter what happens in the course of the day, it simply boils down to how you react to it. Perception is reality and if you can train yourself to maintain and operate in a flow state as much as possible, everything becomes more positive.
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 disposition has an immense effect on their team and their clients because people are looking to them for inspiration and guidance. Positive attitudes lead to positive outcomes. A leader’s role is not just to set the vision for the company but also to be an embodiment of the culture you want your company to have. If you’re leading by example, no amount of trust-falls, free snacks, or company t-shirts can touch that.
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?
One thing I am always conscious of is time, and as I mentioned being protective over your time is crucial. Ben Franklin is quoted with “Lost time is never found again,” which I find immensely powerful, especially today. People can become fixated on the wrong things like money, material possessions and Instagram likes. But if you lose $100, you can always make it back later with a good investment later. However, if you waste an hour or a day you will NEVER get that back, no matter what decisions you make later on. For some people, the time has somehow become the enemy. These individuals wish time would pass by faster- they can’t wait for their day, their shift, their commute, whatever it may be, to be over. This, to me, is crazy. A smart entrepreneur is constantly trying to maximize their time. Every hour is an opportunity to either do something constructive or throw it away. Spending 30 minutes every day on Facebook seems harmless, but over the course of a year, that adds up to 7 days… an entire week staring at a screen that brought you zero benefit. Imagine all the things you could do with that extra week in your year. Time waits for no one, so use it wisely.
Of course, I also love the Twain quote: “Find a job you enjoy doing, and you will never have to work a day in your life” because it does a good job of summing up the life of an entrepreneur. Entrepreneurs don’t do what they do to have a job. Jobs are everywhere, and they’re easy. Being an entrepreneur is hard, but it makes it a hell of a lot easier if you enjoy it. If you’re not enjoying all of the ups and downs, you simply won’t succeed.
How can our readers further follow you online?
I can be found on Twitter at @OptimizePrime, Instagram @OptimizePrime, or connect with me on LinkedIn at https://www.linkedin.com/in/optimizeprime/. My personal site is optimizepri.me where I write about digital marketing, business, and technology.
This was very inspiring. Thank you so much for the time you spent with this. We wish you continued success and good health!