Celebrate the small wins – like a demo booking or positive customer feedback. Remember that success comes from progress that builds upon itself over a long period of time.
Holman is a software engineer turned entrepreneur with a love for education. He currently is the Founder/CEO of BoostMySchool, the all-in-one fundraising platform for schools.
Holman started his tech career in Silicon Valley as a senior software engineer at several venture-backed startups, one of which was acquired by Google. When his former high school needed to raise money to cover funding lost due to budget cuts, he built the first version of BoostMySchool to assist with their efforts. Since then, BoostMySchool has onboarded K-12 schools and universities coast-to-coast and helped them raise millions of dollars.
Holman’s background is in math/science and he holds a B.S. in computer engineering and mathematics from University of Maryland. He loves STEM competitions and competed on the university team in the ACM-ICPC World Programming Finals. He credits a lot of his professional success to his education, which is why he strives to make a difference in the education industry and help out students who traditionally may not have access to a strong education.
In his free time, Holman likes to sing and play guitar, play pick-up volleyball, and volunteer with local non-profits that help underserved students work towards STEM careers. His life motto is: have fun, be thankful, and improve the world the best you can.
Where did the idea for BoostMySchool come from?
The idea for BoostMySchool came from my former high school, which had lost funding due to government budget cuts. When alumni and parents started to solicit donations to cover the lost funding, I worked with them to build the first version of BoostMySchool to assist with those efforts.
After the platform helped my former high school double the number of its annual donors, I decided to cold call schools in the area to gauge the broader demand for such a platform. One of the biggest moments for both the company and my growth as an entrepreneur was when we signed our first deal that originated from a cold call. We’ve since expanded across the U.S., helping both K-12 schools and universities raise millions of dollars.
What does your typical day look like and how do you make it productive?
I start every day by planning out what I’m going to work on. I look through our company calendar andtask list to get a sense of priorities, which helps me decide what to work on between meetings.
One strategy that helps me be more productive is to group similar tasks together and work on them at certain times in the day. For example, I love working on creative tasks (coding, marketing, etc.) in the morning because that’s when I have a clear head.
How do you bring ideas to life?
The very first and most important step of working on an idea is deciding if it’s worth working on. It’s easy to get caught up in the excitement of a fresh idea, which is why we build in time between idea conception and idea execution. The idea must be in line with BoostMySchool’s goals before anyone devotes execution time to it.
After deciding that an idea is worth working on, we break out the idea into smaller chunks of tasks. While the thought of taking on a huge idea can be daunting, dealing with smaller tasks makes the execution seem more manageable and it ensures that progress is being made towards the larger vision.
What’s one trend that excites you?
I love that customers are expecting businesses to become more authentic and transparent.
Even though we need to put more resources into brand presentation as a result of this trend, it excites me because this is a win-win for BoostMySchool and our customers in the long run. We’ve seen that more transparent we are, the more our customers will trust us, which leads to happier customers and more referrals.
What is one habit of yours that makes you more productive as an entrepreneur?
I devote time each month to meeting people outside of my network. I find it helpful to talk to new people about BoostMySchool because it gets me out of my day-to-day line of thinking. Frequently, the person suggests an idea or perspective that I had never heard before!
I generally accept intros from friends or cold meeting requests if the person seems genuinely interested in connecting. If I feel like I’m not meeting enough new people in a month, I’ll use a networking platform like Lunchclub or Meetup to expand my network.
What advice would you give your younger self?
Never underestimate the power of networking.
This may be surprising given the answer to my last question, but I used to think networking was too impersonal. I even refused to get a LinkedIn until last year! But I’ve since realized that this mentality is overly cynical and not everyone thinks of networking in a purely transactional manner. Many people in my network have been thrilled to provide help when I ask for it and I’m continually grateful for their support.
Tell us something that’s true that almost nobody agrees with you on.
Every entrepreneur should learn to be great at cold calling, even if it’s not needed by the company. Cold calling helps build up a resistance to rejection and also teaches the value of a concise pitch.
As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?
Celebrate the small wins!
Especially in the early stages of a company when everything seems like a struggle, it’s easy to lose belief in oneself and the company vision. I’ve found that enjoying the small wins – like a demo booking or positive customer feedback – has kept me going through the tough times. Remember that success comes from progress that builds upon itself over a long period of time.
What is one strategy that has helped you grow your business?
Asking current customers to help us out. Prospective customers always prefer to hear from current customers rather than from us, so we’re proactive about asking our current customers for testimonials and case studies that we can use in our marketing. In addition, we occasionally ask our current customers to put in a word for us within their professional network.
We’re very thankful to our early customers for believing in us and for spreading the word about BoostMySchool. Our job moving forward is to continue to repay them with an excellent customer experience!
What is one failure you had as an entrepreneur, and how did you overcome it?
A huge mistake I made in the early stages of BoostMySchool was trying to do too much myself. I’m a solo founder and I naively thought that I’d be able to master all facets of the business – sales, marketing, customer success, product, engineering. That mindset hindered initial growth and led us to miss our targets in the first year.
Now, I have almost the opposite approach as I look to delegate my responsibilities as much as I can. In addition, whenever we realize that we’re lacking experience in a certain aspect of the company, we bring on a consultant to make up for that experience gap. Consultants help us build out best-practice processes that our employees can adopt in the future.
What is one business idea that you’re willing to give away to our readers?
I’d be excited to go to a Chinese restaurant with personalized fortune cookie messages from the waitstaff. For example, if a waiter overheard me talking about BoostMySchool, the message in my fortune cookie could be “You will receive an angry customer support email at 4:31pm tomorrow”.
What is the best $100 you recently spent? What and why?
A light alarm clock. I’ve always found it easier to wake up via natural light and recently discovered that there are alarm clocks that turn on a light in addition to playing a sound. I splurged for the “Upgrade Pick” on Wirecutter and have definitely noticed that I am less groggy when I wake up!
What is one piece of software or a web service that helps you be productive?
Toggl – a simple time tracker. Back when I was freelancing and working remotely with no co-workers, I used Toggl to hold myself accountable to the hours that I’d say I’d work. Even though I’m now full-time at BoostMySchool, I still track my work hours every day because it feels like I immediately switch into work-mode once I start the timer.
What is the one book that you recommend our community should read and why?
“Never Split the Difference” by Chris Voss. This book was recommended to me as a must-read for salespeople and I couldn’t agree more. The main idea is that empathy and active listening are key in any type of negotiation: personal or professional. I recommend this book to all entrepreneurs since I believe that an entrepreneur’s main responsibility is to sell – whether it’s to customers, employees, media, partnerships, or investors.
What is your favorite quote?
“Education is the most powerful weapon which you can use to change the world.” – Nelson Mandela.
- Never underestimate the power of networking. There are people in your network who want to help out, just make sure that you show your appreciation for their help.
- Celebrate the small wins – like a demo booking or positive customer feedback. Remember that success comes from progress that builds upon itself over a long period of time.
- Your current customers will help you grow your company as long as you continue to deliver an excellent customer experience.
- Don’t try to do too much yourself and delegate as much as you can.
- Read “Never Split the Difference” to improve your ability to sell.
Company website: https://www.boostmyschool.com