An interview with Maria Angelova
Take time. Be patient with difficult decisions.
As a leader, some things are just unavoidable. Being faced with hard choices is one of them. Leadership often entails making difficult decisions or hard choices between two apparently good paths. What’s the best way to go about this? Is there a “toolkit” or a skill set to help leaders sort out their feelings and make the best possible decisions? As part of our series about “How Leaders Make Difficult Decisions,” we had the pleasure of interviewing Jaideep Singh.
Jaideep Singh is the CEO and co-founder of FlyFin, the world’s #1 AI-powered mobile tax service for freelancers, creators, self-employed and gig workers. Before FlyFin, he was an early adopter of AI/ML as he built Spock, the industry’s first and largest people search engine, indexing over 1 billion people. As both a venture capitalist and entrepreneur, Jaideep focuses on finding disruptive industry startups to spend his time in, creating more than $3B in value for companies. These disruptive companies have ranged from wireless LAN to AI Robotics, deep learning search engines, and SAAS. He has a B.S. and M.S. in computer engineering from the University of Arizona and an MBA from the Wharton School.
Thank you so much for your time! I know that you are a very busy person. Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?
I’ve dreamed of becoming an entrepreneur since I was a kid. At one point, I even considered dropping out of college to help start a restaurant chain. Thankfully, I was already immersed in the software development culture and was drawn to its dedicated environment. This made me realize that I wanted to start a software business. What I quickly learned was that the software business is a complex one. So I embarked on a years-long quest that eventually allowed me to develop the deeper product and business skills I would need to continue my entrepreneurial journey. Some people take a circuitous route to find their passion, but I always knew that starting my own company was what I wanted. It was a driving force.
I’m a serial entrepreneur and investor, so as they say, this isn’t my first rodeo. Before FlyFin, I was an early adopter of A.I. During the rise of Web 2.0, I built Spock, the industry’s first and largest people search engine. At that time, Spock indexed over 1 billion people, representing 1.5 trillion data records. As both a venture capitalist and entrepreneur, I’ve focused on finding disruptive industry startups to invest in and have had the opportunity to start several companies and invest in many others.
So flashback before FlyFin, the idea for the company emerged when I was looking to start my next company. I kept mulling over a list of existing consumer pain points and what software could solve them. I’d spent more than one year kicking around and vetting various startup ideas. Tax time was coming up, and I was close to the deadline to file my taxes. And this idea that I had before came up again; Once again, I was stressing out about putting together a spreadsheet of tax data to hand over to my CPA. For most taxpayers, this annual process is a real pain. I hated dealing with taxes and was certain that most people felt the same way.
So I started thinking about the parts of the process that can be automated. I wanted to find a better way to stop stressing out yearly over my taxes. I also thought about how many people could use this. After some research, I discovered that the number is massive; in other words, there’s a big pain point for many people. This epiphany was important because I wasn’t just trying to build another software company. I wanted it to have a serious impact on people’s lives.
The solution I envisioned also needed to be slightly better and revolutionary. In my experience, people don’t change their behavior unless something is radically different. The third and most important piece was that even though I have experience in A.I. and machine learning and building companies around them, I really needed a strong co-founder steeped in these technologies. My co-founder, Sachin Rajendra, is an AI/ML expert on information retrieval, entity extraction, NLP and computer vision. When I met him, I realized we could be a killer team and develop a market-leading product.
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful for who helped get you to where you are? Can you share a story?
Thank you for all that. Let’s now turn to the main focus of our discussion. Can you share with our readers a story from your own experience about how you lead your team during uncertain or difficult times?
My co-founder at FlyFin, Sachin Rajendra, and I founded the company just before the pandemic started. At that time, it was just us co-founders. We landed funding in the middle of the pandemic and then had to start building a team. I found it a little challenging to build a team remotely. Typically, when we assess candidates in person, we like to have the candidate in a room, and we give them complex problems to solve in real-time, on a whiteboard, under a specific time limit. I want to assess their methodology and how they approach and solve problems. So the whole structure of sourcing and interviewing people adds to building in-person chemistry, and because of the pandemic, our preferred hiring structure got disrupted. And while video adds to building human chemistry, it’s still not the same as in-person. So I found building a team remotely at the very early stages challenging, including:
1. Building a team
2. Getting the team to work productively
3. How to ensure the teams have interesting work and get the feedback they need to be productive.
4. Through this process, we experienced some hits and misses; some people couldn’t adjust to working remotely.
Did you ever consider giving up? Where did you get the motivation to continue through challenges? What sustains your drive?
I never considered giving up at all. If anything, our optimism builds with every passing month. My drive and that of my co-founder come from the positive feedback that we are seeing huge demand for the product, our users and the market. Also, having done it before, I could compare this journey with previous entrepreneurial journeys. And I found others were more challenging compared to building FlyFin in terms of user perception or market acceptance of our product.
Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader?
I have a few examples.
1. Taxes are a complicated space. We had to consider whether FlyFin should go out and raise more money in the middle of a pandemic. More seed capital than most companies and hustle to do this raise. Our success will be correlated to how strong a product platform we can build. This was a strategic and difficult choice. There aren’t too many tax companies because it’s a very complex endeavor: building a tax management app, coupled with A.I., and then automation and CPAs on top of all of this — it’s a very complex space. I find being focused on raising adequate capital, even with doubts about whether or not to raise more funds. Things could have gone either way during this time.
2. Building a large, sophisticated platform required not just adequate capitalization but an intense discipline on spending. Did we want a geographically disparate workforce versus work from home policy? FlyFin has its team widely distributed. Our employees are based in Silicon Valley and India. We found that people wanted to come in and work from a central office. However, they also valued the benefits of working remotely. They just need to be productive. There is so much talent at a global level. We offer some centrality for employees who want to come into an office but also enable people to work from home.
3. As a leader, facing difficult decisions and having the courage to make tough choices are essential. One such decision I made was to let go of a highly-skilled, experienced employee. It was a hard decision, and I agonized over it for several months. However, retrospectively, it was the right decision for the company, allowing us to move forward and continue growing.
What process or toolset can a leader use to make a choice between two difficult paths?
No one should make any difficult choice quickly. You have to take your time and not rush this process. I recommend talking to as many people as possible. And those you speak to don’t always have to be the “right” people. This process can help you crystalize the issue. Research on your own if you still need information. Most importantly, take your time.
Do you have a mentor or someone you can turn to for support and advice? How does this help? When can a mentor be helpful? When is this not helpful?
Strong company leadership is the best place to look for input on matters. It’s good to have terrific people on your board. After all, they are one step removed but still have enough context on the problem. Also, tap your network of friends who are entrepreneurs.
What would you say is the most critical role of a leader when faced with a difficult decision?
One key role leaders have to play is to take a stand and then sell that position to all the stakeholders around them and convince them of it so that everyone is on board. For instance, there are so many different paths on the product roadmap. There can be really experienced people and inexperienced people from whom you want to obtain feedback. Do a lot of data gathering, etc., to gather an abundance of data. There is always an abundance of data. Even from there, you must put a stake in the ground on your position and sell it. Also, acknowledge when you’re wrong. You want to aim to ensure your ratio of being right versus wrong is high.
Do you ever look back at your decisions and wish you had done things differently? How can a leader remain positive and motivated despite past mistakes?
Learn from the mistakes, not by yourself but by discussing them with the broader group and leadership team. By being transparent and open about mistakes, one can learn. FlyFin does this very diligently in product and marketing. Often, FlyFin will review some of their previous tests, checking to see if it is a new idea or one the team already tested but didn’t perform well. Sometimes what seems like a new idea is an old one, but reviewing previous testing of ideas, can give you insight into the chances that these new ideas will work or are the same old ones.
What is the best way to boost morale when the future seems uncertain? What can a leader do to inspire, motivate and engage their team during uncertain times?
It’s essential to keep the noise out. You have to focus on your problems and work on executing really well. Do a better and better job executing. At FlyFin, the team does weekly metrics reviews, and every month or two, there is an all-hands meeting to review everything done as a company. During uncertain times presents an excellent opportunity for team building. There’s a lot more talent available. It’s a great time to upgrade one’s skillset as a team. For example, we have experienced engineers, product managers, and marketing people we’re interviewing now. And we’re bringing them on, replacing others who weren’t as motivated. We’re bringing on more experienced people selectively.
Can you share 3 or 4 of the most common mistakes you have seen other businesses or leaders make when faced with a hard decision? What should one keep in mind to avoid that?
1. Spending money for growth: having the financial discipline to do a 180-degree turn and suspend growth for a while — for profitability. I think a lot of people get this one wrong.
2. Managing expenses: It’s easy to dial up the spending but when there are downturns when you need to save. And it’s hard to be even-keeled when it comes to spending.
3. Give up too soon: Whether it’s taking a lowball offer to sell the company or shutting it down too prematurely.
Here is the primary question of our discussion. Based on your experience and success, what are the five most important things a leader should do when making difficult decisions? Please share a story or an example for each.
1 . Know more. Get more data.
2 . Reach out to as many people as you can. Discuss the decision with as many smart people as possible — whether they know your business or not.
3 . Take time. Be patient with difficult decisions.
4 . Play the long game. Sometimes you have to play the long game compared to the short game. This approach means taking calls that reduce conversions in the short run but will keep your users happy. This path can build more trust in and protect your brand. Sometimes, it’s easy to make outlandish offers just to get more people to subscribe and use your product. However, in doing this, some people could be disappointed. Dial a little more toward the long game, and, yes, the immediate conversion may be lower, but in the long run, you’ll gain the trust of your users. This isn’t an easy decision because our focus tends to be daily and short-term.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
I’m a big fan of Ben Franklin. After all, he was an entrepreneur, philosopher, scientist, diplomat, inventor, etc. I have two favorite quotes by him.
1. A penny saved is a penny earned. As cliche as this sounds, it’s an excellent way to operate your life and business. It brings a value orientation toward things. Applying this can be challenging.
2. There are only two certainties in life: death and taxes! As an entrepreneur, I had two options and didn’t want to focus on death, so my focus became taxes.
How can our readers further follow your work?
Instagram: https://www.instagram.com/flyfin_tax/
LinkedIn: https://www.linkedin.com/company/flyfin-ai/
This was very inspiring. Thank you so much for the time you spent on this. We wish you only continued success.
Thank you for the amazing opportunity!
About The Interviewer: Maria Angelova, MBA is a disruptor, author, motivational speaker, body-mind expert, Pilates teacher and founder and CEO of Rebellious Intl. As a disruptor, Maria is on a mission to change the face of the wellness industry by shifting the self-care mindset for consumers and providers alike. As a mind-body coach, Maria’s superpower is alignment which helps clients create a strong body and a calm mind so they can live a life of freedom, happiness and fulfillment. Prior to founding Rebellious Intl, Maria was a Finance Director and a professional with 17+ years of progressive corporate experience in the Telecommunications, Finance, and Insurance industries. Born in Bulgaria, Maria moved to the United States in 1992. She graduated summa cum laude from both Georgia State University (MBA, Finance) and the University of Georgia (BBA, Finance). Maria’s favorite job is being a mom. Maria enjoys learning, coaching, creating authentic connections, working out, Latin dancing, traveling, and spending time with her tribe. To contact Maria, email her at angelova@rebellious-intl.com. To schedule a free consultation, click here.
Jaideep Singh Of FlyFin On How Leaders Make Difficult Decisions was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.