Matt founded SkillSetz in 2018 after spending more than fifteen years as a management consultant and B2B eCommerce technology leader serving Fortune 500 clients across a broad range of industries. Matt’s completely unplanned career path gives him a cross-dimensional understanding of the $1T B2B Professional Services market given his time spent selling and delivering enterprise procurement advisory services
, leading cross-functional digital transformation projects, and designing complex B2B eCommerce strategies for dozens of iconic, publicly-traded business customers. Matt currently leads the SkillSetz team from the company’s headquarters in Naperville, Illinois where he also lives with his wife Ariella and their three young children.
What is SkillSetz all about?
SkillSetz offers businesses of all sizes a one-stop shopping experience for all of their business service needs. One way to think about it would be to imagine Amazon and LinkedIn getting tossed into a blender together. SkillSetz would be the smoothie that combines the B2C usability of the Amazon shopping experience, with the access and visibility to highly qualified professionals that LinkedIn is rightfully renowned for. We will never be as successful as either of those two iconic companies, but they are important role models for us as well as an inspiration.
Our business customers enjoy simple and transparent access to a deep network of world-class professionals whose experience, expertise, and talent are available for project-based work. Our purpose is to make it easy for our customers to collaborate on project-based services opportunities, execute any mutually agreed upon work orders, and settle any related transactions – all while ensuring transparency and compliance.
We believe the time is right for corporate America to rethink how they can find and utilize the expertise they need for their specific business challenges. We believe that helping our fellow professionals commercialize their natural abilities to create value for themselves and their families is a business idea worth fighting for – especially right now. We also believe that the American workforce is the most powerful, creative, diverse, and innovative talent pool on the planet.
In the last 12 months, we have also now proven that all of us can work from anywhere.
Tell us a little bit about your background and how you started your company?
I have spent most of the last 18 years working as a B2B and Procurement technology advisor for (mostly) Fortune 500 companies and similarly sized private companies. My exclusive focus during my career has been helping these companies better control and manage their corporate spending while making the experience as painless and efficient as possible for their employees.
Along the way, I learned an awful lot about how spending really works in large companies. In 2018, I founded SkillSetz which, in retrospect, was a natural evolution of my experience. It started out as a way for me to use my knowledge, experience, and (as my mother calls it) moxy to help large corporations get their arms around their Services spend – which remains a formidable challenge for most large companies today. The fact that I could help my fellow business professionals by empowering them to transform their own unique natural abilities into meaningful economic value for themselves and their families was icing on the cake.
The company began in 2018 as a really expensive hobby where we began experimenting with some emerging hybrid cloud technologies and applying some of these cutting edge capabilities to some of the common business and process challenges I have seen throughout my career in Enterprise Procurement. By the end of Q1 2019, I had seen enough to know that we had an opportunity to do something very special. Exactly 12 months later the COVID pandemic turned the whole world upside down. I knew instantly that I would be spending the rest of my professional career helping businesses and services providers find each other with SkillSetz.
What was the biggest problem you encountered with your business and how did you overcome it?
This will probably come as no surprise but time and money was the biggest problem when we started building SkillSetz. I set out with the mindset that we were going to build a powerful, marketplace platform that would need to plug and play with the enterprise at scale. I made the decision that I was going to figure out how to fund and grow this business myself and I applied this philosophy to every business decision I made ever since. There is something about human nature that makes us less prone to making bad financial decisions when it’s our own money.
Ultimately, how we really overcame the time and money challenge came down to planning and discipline. When we started building the platform in 2018, my consulting practice was taking up most of my work day and paying all of the bills of both companies. It also was 18 months before COVID so the idea of a Professional Services marketplace wasn’t exactly on anyone’s radar. With that in mind, we decided to play the long game and take our time on the architecture and interoperability strategy.
I made the decision to continue with my active consulting practice while investing 20% of my monthly net income from the practice into SkillSetz. We layout our feature roadmap in 6 month blocks with key milestones and activities in Jira Cloud. All of our applications are synced and integrated with Slack which keeps us all connected all the time. The development team is on a schedule that puts them 8 hours ahead of our team here. The communication set up was key because the costs were negligible and we were always in sync.
Between the summer of 2018 and the onset of COVID in Q1 2020, I would wake up early every morning, grab my coffee, and jump on Slack and Jira to check in on the dev team on the work that happened overnight. Then I would begin my day job providing advisory work to my enterprise procurement clients. At the end of the day, if I thought of anything new or if there was something I didn’t want to forget, I’d drop a note into Slack for the dev team to see when they woke up. I would save my more strategic thinking around SkillSetz for weekends because my brain can’t switch gears that easily.
That’s how we boot-strapped SkillSetz from a whiteboard to production in 18 months. At the end of the day, none of this would have been possible without some really strong trust between myself and the other SkillSetters who helped me build SkillSetz. Yet, it is precisely that trust that really helped me overcome the time and money challenges because I could not have done this without them.
What would you say is the biggest business problem you are trying to solve and how are you solving it with SkillSetz?
The biggest problem we are trying to solve is the clunky, out-dated business process of finding professional service providers that match a specific business problem, collaborating with the right provider on requirements, executing a legally compliant work order, receiving the services, and paying the provider’s invoice.
It sounds pretty straight forward but you would be amazed at how difficult and uncontrollable this process is in corporate America right now – something I learned through 20 years of enterprise procurement consulting. In fact, the $1T Professional Services industry is probably the last industry around that still relies on the “I know a guy” due diligence and referral model.
Overnight, COVID-19 turned this boring procurement challenge from a clunky process problem to a clear existential threat for both sides of the equation. Businesses across the globe are accelerating their digital transformations because how they get things done in this new world has changed forever. For Service Providers of all shapes and sizes, business development and customer engagement are problems that are not going to go away anytime soon.
How is this whole commercial development and relationship structure supposed to work now in this new world with all these new post-COVID frameworks? At SkillSetz we think our platform can help bridge that divide and bring both sides of this huge market together in a way that makes sense for everyone.
What were the top mistakes you made starting your business and what did you learn from it?
When I think back on starting SkillSetz and some of the decisions we made in the early days, I would say that I made two really big mistakes that both cost me.
The first big mistake I made was very early on when we were designing the platform. I did not take the user persona development work as seriously as I should have. I gave it superficial thought – not deliberative thought. That mistake alone cost me about 3 months of development costs because we had to go back and rewrite the personas and then the code when we realized the flaws during UAT. The reason I am so hard on myself for this one is because it was a self-inflicted wound.
The second biggest mistake I made early on was signing on to some SaaS agreements that we ultimately didn’t need. That was just plain stupid. There is never any reason to pay for something until the exact moment you need it, especially in today’s day and age. Businesses change and circumstances change but the one thing that doesn’t change is the fact that once money goes out the door on an expense, it’s not coming back.
What is one thing that you do daily to grow as an entrepreneur?
I spend at least 2-3 hours every day reading quality content. Change is happening so fast now, especially in technology so it is really important to always stay on top of emerging opportunities for – and threats to – your business. I like to think that every lesson that I read that someone else learned is one less lesson that I will have to learn the hard way. I would say this commitment to reading and learning is probably the most important thing I do every day. I feel like I can never afford to stop learning.
What are three books or courses you recommend for new entrepreneurs?
I would say the one entrepreneurship book that probably impacted my thinking and my career the most was Blue Ocean Strategy by Renée Mauborgne and W. Chan Kim. It does a really good job of exploring the idea of innovation in the face of seemingly insurmountable odds and I have seen its application and relevance many times throughout the course of my career. It’s an encouraging read because it shows the entrepreneur how strategy can make all the difference when the market competition is fierce.
The second book I would recommend is Outliers by Malcom Gladwell. I think this book is particularly helpful to entrepreneurs in terms of understanding what it really means to be an entrepreneur and what kind of commitment it really takes. The one interesting takeaway I had from this book is that all of those iconic, famous tech founders who all dropped out of college – they all still put in the time and effort to learn. The idea that their education stopped is a fallacy. They dropped out because they concluded that approach was a better life investment for them – and every single one of them was right.
The third book I would recommend is House of Cards by William Cohan. The book tells the story of the rise of Bear Stearns and gives a fascinating play-by-play account of how it all came apart in 2008. This book has always stayed with me as a cautionary tale about hubris, greed, and cognitive bias. My big takeaway from this book was the exposition of the role and dynamic nature of “confidence” in the business world, and especially on Wall Street.
What is the one thing you wish you knew before starting your business?
I don’t know if this is applicable to everyone, but I for one tend to be obsessed with data, details, and nuances. As a founder, that passion can be really helpful at times but it can also be really unhelpful at times. If I could go back and talk to myself before starting my business – I would tell myself “Always know your audience.” The reason I would say this is because one of the things that makes entrepreneurs special is the insane amount of passion and focus they have. The problem is that everyone that entrepreneur talks to is not in that same mental space.
When I think back on my career, it is clear to me that I wasted an inordinate amount of my time and other people’s time over the years on communications, sales, and networking that, in retrospect, was all doomed to fail because I didn’t know my audience. I wasn’t effectively communicating with them because I wasn’t thinking about or considering their perspective. I was too busy selling whatever vision I had and looking for affirmation. I tell my kids all the time that you can’t talk and learn at the same time. Similarly, you can’t know your audience unless you listen to them.
What has been your most effective marketing strategy to grow your business?
I would say that the most effective marketing strategy for SkillSetz so far has been just telling our story. Obviously, we didn’t plan for COVID to come along last year and accelerate the normalization of work from home and remote working relationships in corporate America. We considered ourselves fortunate to have been in a place where we were already pretty far along on our platform build. We felt like SkillSetz was set up in a great position to help lead this transition to the future of work.
Since the pandemic began, we have not had to spend a lot of time explaining to people why SkillSetz is timely and relevant – so telling our story is the best (and most powerful) thing we can be doing to grow our business. That’s because when we do that, people are telling us their stories.
They are telling us about how their professional life has changed, how their home life has changed, how their view of the world and the future of work has changed. What’s really cool about this is the growing affirmation of how we are really all in this together. That is why I would say that professional networking has been the most powerful marketing tool thus far.
If you only had $1000 dollars to start a new startup, knowing everything you know now, how would you spend it?
If I assume you have a phone, laptop, and wifi then this is an easy one – and I would have saved myself so much money and heartburn had I known this sooner. I would take $250 and have Legal Zoom handle my incorporation. Then I would take the other $750 and buy a subscription to the Founder Club by Product Hunt which gets you access to a ton of free resources and subscription credits for a wide swath of cloud services to get your business kick-started. They literally have something for everyone in the tech startup scene and the ROI on that subscription translates to 6-12 months of free runway on your core technology related expenses. There is literally no better way for a startup team to stretch your capital than grabbing that subscription.
What’s your best piece of advice for aspiring and new entrepreneurs?
The best piece of advice I can give any new entrepreneur is to make sure you really want this. I don’t mean wanting the success, money, and professional shine that comes with building a winner. Thats easy – who doesnt want that? I mean you have to want to do all the ugly, tedious, inglorious things – not because you want to – but because they must be done to succeed.
There is no substitute for the insights, instincts, and confidence that are derived from putting in those mental reps. You will not see any return on that pain in the short term, but you also will not see any value gains in the long term without putting those reps in every day.
What is your favorite quote?
My favorite quote can be attributed to Mike Tyson who, if you haven’t noticed, is aging like a fine wine. When he said “Everyone has a plan until they get punched in the mouth” he meant it quite literally. I have often thought about how (figuratively) true that statement is.
As someone who spent the better part of the past 20 years working on transformational projects for large companies, I know all too well how a figurative punch in the mouth can throw hundreds of hours of project planning out the window and make you look weak and unprepared. Every time someone tells me that the project plan is all buttoned up, I hear Mike Tyson’s voice in my ear.
How is running a tech company different than what you thought it would be?
It is WAY more fun that I expected it would be. I think this is because we are purpose driven and everything we do is designed to help our fellow professionals – so it really doesn’t feel like work at all. The other thing that I really like about running a tech company is that it is much easier to rely on others to help you.
Most of my career has been spent doing advisory and consulting work which I really couldn’t farm out. As a result, I was relatively limited in the scope of things I could take on at any given time. Today, I have an entire squad of absolute rock stars on our team helping us build SkillSetz and so many things get done without me even knowing about them. It’s an amazing feeling to watch a community rise up organically right in front of your eyes.
How can readers get in touch with you?
I plan on spending the rest of my professional life helping businesses and professionals find each other and create economic opportunities for each other on SkillSetz. That is the only place I want to be and that is where you will always find me. I’m also on LinkedIn and Twitter.