Skillsquare Founder Tamir Jacob Shares His Top Advice for Entrepreneurs

Starting your own business can be an exciting but challenging undertaking. Here to tell us about his experience navigating entrepreneurship is Tamir Jacob, founder of Skillsquare. Tamir has mentored for Techstars, is part of the Intenational Association of Innovation Professionals, currently serves on the International Council for Small Business and is a member of USASBE, the United States Association for Small Business and Entrepreneurship.


Welcome Tamir! It’s an honor to have you joining me today.
I have to start by asking, what is Skillsquare?

Great question Anastassia.

Skillsquare started out as an idea to curate content for early stage entrepreneurs. The idea came out of a personal pain point. I felt that there was really not many resources for people out there for wantrapraneurs/early-mid stage entrepreneurs starting out. Another option was corporate employees who were tired of their monotonous corporate job and wanted a place they could go and test the waters of entrepreneurship risk-free.

The main problem I found from talking to people, was that starting out they were clueless of which direction to go and what to learn. There was already so many existing resources on places like Youtube on entrepreneurship. But guidance and direction were scarce.

People wanted to know what resources were relevant and when. Normally mentors would fill in this role. But if you are an early stage entrepreneur and don’t yet have a solid network, or you are in a full time job, and you don’t have the time to do an accelerator because you are working full-time, finding the right mentors and getting reliable entrepreneurship advice can be a problem.

I figured curating content specific to entrepreneurship, with learning feeds and group discussions would be a viable solution to what I thought was a big issue.

I was actually shocked that this hadn’t already been done.


How do you differentiate it from platforms such as LinkedIn Learning, Udemy, and Coursera?

Skillsquare’s initial plan was to partner with the accelerators and incubators. I figured if we could design a better way for them to distribute content to their cohorts, they would upload their content and partner with us, in addition to providing us with exclusive content and access to potential core customers.

This all sounded great in theory! Except I was an amateur to entrepreneurship at the time and swimming out of my depth.

We made one of the classic mistakes; “Failure to validate your riskiest business assumptions first. If I were to go back in time I would ask myself first; What are the assumptions that if I am wrong the whole business would flop?”

The good news at least was that we were right on our first implied assumption: accelerators had no effective way to distribute content to their cohorts. Some were using Slack and they didn’t like it much. Actually one the biggest accelerators loved the idea of Skillsquare and signed up straight away. The team was ecstatic!

Unfortunately the victory was a Pyrrhic one and the excitement was exceptionally short-lived.

We were very wrong about our second assumption that early stage entrepreneurs were our core customer. The cohort entrepreneurs themselves didn’t really care about what we were doing that much and were much later stage than we initially expected them to be. They used Slack to communicate and they liked it. They also used the accelerator’s mentors with office hours for advice, so they didn’t feel they needed us!


At the time we had already developed 3/4 of our product and we had tailored it to the accelerators primarily. In addition we had blown through the large chunks of our capital and to top it off, nobody cared enough about what we were doing to pay us anything.

We were also wrong about a few other assumptions.

A big one being that the accelerators had content to distribute. Apparently many of the top accelerators are actually mentor-driven, as opposed to curriculum-driven.

We were shocked. The accelerators literally had no actual content to give us to upload!

We had tailored our product to them, hoping to acquire exclusive content that they didn’t have, targeting a customer that didn’t care less.


The way we intended to differ was by curating exclusive entrepreneurship training and discussions from the brains behind some of the world’s top billion dollar companies.

It just didn’t work out how we envisioned it. The good news is that we learned to take the riskiest assumption mapping exercise extremely seriously. We are now revamping the business model!


What led you to start Skillsquare and what were you doing before you decided to become an entrepreneur?

I feel like as kids we always tend to end up the ‘polar opposite’ of our parents.

I never came from a rich family growing up. My mum was a social worker and my dad was an electrician. My parents are cautious people. Perhaps it is only right that their son was more audacious.

I started my first business at sixteen. I saw a bunch of my classmates at school were going to a nightclub. I figured someone must be making money from it. Why not me?

My mum told me “You’re insane.” She told me, “You can’t start a business. You don’t know anything about the club industry.”

Luckily I didn’t listen! I called up the club anyway. The next week, my classmates came in on my guest-list at the door. The club paid me $20 per person that came. I couldn’t believe it. Luckily they had no idea I was only sixteen. Truth be told, I don’t think they cared. They just wanted the headcount.

All I know is that I made some good pocket money that week and the following next few years going out, getting paid for it and having fun at the same time! I ended up running my nightclub management company in London all the way up until I moved to America after college. It sure worked well for my college survival budget!

When I moved to America I went into retail sales for a bit to become indoctrinated with the culture. I hustled my way to AGM (Assistant General Manager) at Burberry in less than two years. I can’t entirely understand that one. I think it might have had something to do with the British accent. In any case one day I straight up quit my job in retail and vowed I would starve or find a way into finance.

One week before I was to go broke I made it in into finance!

Later on…

I thought of the idea of Skillsquare and I couldn’t shake it. Up until that point I was always held back by the idea that I needed money to start a business. I figured however that this was no excuse for not getting started, as I must be missing a lot of steps before the money was needed! So I decided to just focus on making a first step. I asked myself, “What is the smallest thing I can do today to move the direction of my goal?” Then I did it!

The next day I decided I would take another small step and then I did the same thing the next day and the day after that and suffice it to say, progress compounded and the train has long since left the station!

A quote that I live by now is “You don’t need to see the whole staircase to take the first step.” It really helps you avoid getting overwhelmed by scenarios that may or may not happen and focus on what matters.


That’s an excellent quote to live by. What about next plans for Skillsquare? In what areas are you hoping to grow most in the coming year?

The school of hard knocks can be an effective mentor. It has helped me realize that you only have a limited amount of pivots in a startup. That said I am working on a few other projects alongside Skillsquare in ecommerce. For now we are in the process of revamping the business model of Skillsquare. I will say that the learning process so far has been epic. It is indeed true that education can definitely be expensive in America. Especially self education!

In 2018 one of my personal goals is to read a book a week. I realized last year that it is important to focus your learning on specific topics for set periods of time for it to be more effective. It allows you to go deeper on a subject and creative connections form better.


When we first talked, you mentioned that you worked in finance while also running your startup. How did you balance both roles? Do you see your role in finance as a type of insurance towards your leap into the startup world? 

I guess you could see a job in finance as insurance, or you could see it as motivation. I don’t think $100K buys too much nowadays. Maybe a couple of trips to Whole Foods a week. But it isn’t good for much else. I think at some point you have to decide if you want to make a living or you want to make a life. Entrepreneurship is the way forward to creating a dream life for yourself and your family.

The real work typically starts when I get home. I see the job as just a chore. When people ask me what I do typically I tell them that ‘finance’ is my hobby and entrepreneurship is my job.”

The funny thing is I actually just gave my notice in to my job in finance. Straight up, just said to my CFO “This is boring, I’m done.”

I was honestly tired of the corporate game playing, ‘sponsored inefficiency’ and time wasting. I realized entrepreneurship was a bit like learning a language. No one ever learned to speak French fluently from reading a book. The only way to truly learn French is to live in France and immerse yourself in the culture!

I figured at some point I needed to make the leap and just immerse myself in entrepreneurship to really embody it, so why not today? The ducks will never align exactly in a perfect row. So I fired my boss and now is where the really fun challenges begin.


During your career, have you ever had moments of self-doubt where you’ve questioned either your abilities or the path you’ve charted? What did you do to overcome such moments?

Yes. My first day as a financial analyst I sat down at my desk, looked at my computer and said “Is this all there is? Is this what I’ve been working so hard for?” Suffice it to say, my number was drawn from that moment onward!

I try to force myself to be uncomfortable. I figure if I am too comfortable I am not growing and that is bad! I believe that on some level, everything you ever wanted is on the other side of your fears. Sometimes you have to just believe everything will work out and not think about how you will make money or get on your feet and just take a leap of faith.

I believe that sometimes when you begin to flow with the current of life, instead of against it amazing things happen. True wisdom is knowing when to quit. Understanding when the game you are involved in is no longer worth playing anymore and saying “I’m out.” That about encapsulates my feelings about corporate America! It is safe to say, in those moments you must leap. In a year you will see me in a mansion or on the street! But I’ll be smiling either way, because I will have given it my best and that is all you can ever expect of yourself.

I think another really important thing is how you frame fear and the feeling of security. To me a 9-5 job represents the ultimate insecurity. What could be more insecure than entrusting your future to openly complacent leaders that just want to coast. I don’t want to be around when karma catches up to the big companies! I would rather be in control of my opportunities. I can control how hard I work and what I learn. What could be more fulfilling than directly seeing the impact of my own learning on my business? I think entrepreneurship and continuous self development are the ultimate job security.


What does your typical weekend look like?                

I do a business model canvas of a different company everyday (weekend or weekday) to practise using There is a bunch of business model canvases of famous companies already mapped out by some cool entrepreneurs at They are good to use as a check.

I journal daily my favorite learning from my readings.

I am not much of a morning person. At least, not now. I stay up super late and drink lots of espresso. The girlfriend hates it. But she puts up with me!

Weekends I mostly read, see friends, read articles, work on my businesses, occasionally walk, occasionally attend conferences and mentor at startup events.


As a TechStars mentor and a partner at MassChallenge, I’m sure you’ve had an exposure to many budding entrepreneurs with their sight set on getting their startup off the ground. What are some of the most common hangups or misconceptions that you witness?

Indeed. The most common hangup is I see so many entrepreneurs overly focus on their solutions. Many don’t realize starting out that their business idea is really an implied solution to a problem and it may not be the best one. You almost have to back track from your ‘business idea’ to the problem that you think you are solving first and for whom! It is really important to validate that the customer you have defined actually has that problem you think you are solving to a strong degree and that it causes them enough pain that they are willing (and have budget) to pay to have it solved.

The other misconception is that you need money to get started. I always tell people THINK SMALL. So many entrepreneurs think huge starting out and then seek funding to make up the difference between where they are and where they think they should be.

I think it comes down to asking better questions. Instead of asking how do I make a million dollars? At first entrepreneurs should be asking; How do I make my first one hundred dollars? How do I acquire my first customer? They need to adopt a ‘Think Small’ mentality. Then scale as they go. I am not a fan of VCs in general. I will say this though. The only time investor funds should only ever be taken by a start-up are to scale it. But this is later on after business model validation has taken place.


Henry Ford, Dale Carnegie, and other notable leaders have claimed that failure brings opportunity and is a stepping point to success. In the same vein, what would you consider one of your greatest failures and what was the lesson you learned from it?

I think failure is often a matter of perspective. If a business fails, is it the business that has failed, or the entrepreneur?

The way I see it, you are just the learner. The business is the failure!

I have therefore found it wise to keep ‘the sense of the self’ from being entangled within business or being tied to a specific outcome by this way of perceiving things.

If failure is to be understood as giving up on something; I would say I have truly failed in a big way at being part of the corporate world. I generally suck at being a conformist and I’m really bad at prioritizing showing up, as oppose to working efficiently. I would rather just do my work in a quarter of the time and listen to an audiobook. From this experience I have learnt that I should probably not be there!


What is one of the best pieces of advice that you’ve received from a mentor, a colleague, or someone you’ve looked up to?

I absolutely love Peter Sage. He is a mentor of mine now and someone I thoroughly identify with. He taught me that it is OK to build your plane as you fly it and that you will be far more successful in business if you are extremely audacious; meaning that when you “burn the boats”, you will always find it much easier to “take the island”. Some would call Peter an ‘extreme entrepreneur!’ I am proud to call him a mentor.

Peter taught me that you don’t need to know the ‘how’ before you do something. Just the end goal. The ‘how’ is not your responsibility. There is a great episode here that Peter would want me to share with you and your readers.


What is one book or podcast you’d recommend our readers to start 2018 with?

For a Podcast, I love the Masters of Scale with Reid Hoffman.

Really enjoyable and filled with lots of gold nuggets of wisdom.

For a Book, I think the most beneficial book on entrepreneurship that I recently discovered was a book called 24 Steps to a Successful Startup by Bill Aulet. I wish I would have found it years ago! Bill is the head of MIT entrepreneurship, a phenomenal mentor and human being. This is the best step by step guide to entrepreneurship for those starting out that I have found. A must read for would be entrepreneurs.


Finally, is there a way for our readers to personally get in touch with you to ask questions and get additional advice?

Your readers are welcome to contact me on LinkedIn anytime!

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