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Benjamin Yoskovitz of Highline Beta: “Believe in Yourself”

Believe in Yourself. I don’t think you can be an entrepreneur without believing in yourself and having conviction in your ability to be successful. This doesn’t mean you won’t feel like an imposter sometimes (you probably will) but fundamentally I find that successful entrepreneurs are those that simply believe. How do you get belief in […]

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Believe in Yourself. I don’t think you can be an entrepreneur without believing in yourself and having conviction in your ability to be successful. This doesn’t mean you won’t feel like an imposter sometimes (you probably will) but fundamentally I find that successful entrepreneurs are those that simply believe. How do you get belief in yourself? That’s another extremely tough question. But if you don’t have true conviction in your ability, you may find you have more lows than highs.


Being a founder, entrepreneur, or a 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 Ben Yoskovitz, an entrepreneur, investor and author (Lean Analytics) with over 25 years of experience in the tech space. Currently, he is a Founding Partner of Highline Beta, a hybrid venture studio and venture capital firm. Previously he was VP Product at VarageSale and GoInstant (acq. by Salesforce), CEO at Standout Jobs, and co-founder of an early-stage accelerator, Year One Labs.


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?

I fell into entrepreneurship somewhat by accident while attending McGill University in Montreal. It was between my second and third years of university, in 1996, when I met three guys that were looking to start a web development company. I had always been interested in technology and thought it would be interesting to dive in. I didn’t have any particular skills that made me think I would be successful, but even if it had only lasted a short while — as an experiment — I knew I would learn a ton. We formed a company called meep! media, which built websites and web applications. I had no idea that twenty-five years later I’d still be in the tech space building and funding startups. Incidentally, I finished my university degree (a Bachelor of Science in Psychology), while simultaneously working on my company at the time.

What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

I co-founded Highline Beta in 2006 with Marcus Daniels and Lauren Robinson. A few things happened at the same time. For starters, my work at VarageSale ended at the beginning of the year. It was a bit of a surprise for me (a definite low moment), and I found myself having to figure out what to do next. After a couple of months of exploring opportunities, I knew I was ready to start a company. I hadn’t started something for a while (I co-founded Year One Labs in 2010, and prior to that was CEO/co-founder of Standout Jobs from 2007–2010), and I was emotionally ready to do so. I then connected with Marcus Daniels, who, along with Lauren Robinson, were finishing up their investment mandate on Highline VC (a pre-seed fund built atop an accelerator model.) Marcus and I had known each other before but had never worked together. We both wanted to start a new company. We love investing in startups — but didn’t want to be venture capitalists. We love building companies — but didn’t necessarily have a specific idea to pursue. And from our separate backgrounds and experiences, we saw an opportunity to work with large companies and help them build new ventures beyond their core. So we combined all of these elements and launched Highline Beta.

In your opinion, were you a natural born entrepreneur or did you develop that aptitude later on? Can you explain what you mean?

Considering I fell into entrepreneurship by accident, I’m not sure I can say I was a natural-born entrepreneur. Prior to starting my first company, I played things pretty safe — did well in high school, got into a good university to do a science degree, and thought I was on track for medical school. When I got to university, the number of years required to get a medical degree really hit me, and I realized I did not excel sitting in a classroom. But I wasn’t a huge risk taker at the time. Now? It’s definitely a different story. I don’t even see starting a company as terribly risky anymore — it’s fairly inexpensive to do, there’s a ton of support systems in place (i.e., content, communities, etc.) and although there are stories of entrepreneurs selling everything they own and going into crazy debt to fund their companies, you don’t have to go that far to succeed.

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?

The first person that comes to mind is Austin Hill. Austin is a successful serial entrepreneur that I met in 2006. I had left my previous company and was trying to figure out what to do next. He encouraged me to start a new company (which ended up being Standout Jobs) and was my first investor. Prior to that, I had minimal exposure to angel investors or venture capitalists, but Austin believed in me as an entrepreneur. He took me (and my co-founder in Standout Jobs) on a crash course in raising capital, pitching your startup and being much, much bolder and ambitious. I’ll always be thankful for Austin’s support.

What do you think makes your company stand out? Can you share a story?

Highline Beta stands out because we’re combining a few different business models together in a way that’s not been proven. We have an innovation consulting business that works with large corporations, an accelerator business that helps startups and corporates work together, a venture studio that builds startups from scratch and a venture capital fund that invests. It sounds like a lot of moving parts, but together it works, and we’re proving how all of these pieces can fit together successfully and create immense value for our clients, startups and portfolio companies.

A story that I can share is related to an accelerator program that we recently completed with Intuit Canada. We helped Intuit Canada launch the Intuit Prosperity Accelerator, which was designed to help support the financial wellbeing of SMBs and consumers in the wake of COVID-19. We brought on board 8 startups to work with Intuit Canada, and the program was a huge success. At the Demo Day (March 2, 2021), we were lucky enough to have Scott Cook, co-founder of Intuit, present and share his experiences in starting Intuit and stories on perseverance. At Highline Beta, we spend all our time trying to figure out how to connect the dots between large corporates and startups to create value for everyone.

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?

The first thing that comes to mind is perseverance. I’m a grinder. I put in the time, and don’t really quit. When something isn’t working, I know I have to move on (there’s no point “beating a dead horse”) but if you persevere and stick out long enough, you’ll find the right opportunity at the right time and be successful with it.

The second thing is luck. Perhaps luck isn’t a character trait, but I consider myself incredibly lucky. People will say, “You make your own luck,” and to some extent, I think that’s true — probably by persevering!

And finally, I’m a chameleon. Some might call this “being flexible.” When blogging was becoming popular in the early 2000s, I jumped into it and started writing a blog (see: https://instigatorblog.com). I was doing a lot of writing about small businesses (because I was running one), which led to a number of great opportunities. In 2007 when I started Standout Jobs, I started writing about recruiting and human resources and pivoted into becoming a CEO of a venture-backed startup. Again, new opportunities emerged from that (and some failures too!) I’ve changed careers quite a few times, and transitioned my skills and experience into different areas, from running an accelerator to being an author, to investing, etc.

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?

Nothing comes to mind immediately, but I will say this — there are always doubters. For example, when you go to raise venture capital, you’ll get rejected far more often than you’ll receive funding. That’s how the venture capital business works. It doesn’t mean all of the venture capitalists that said “no” are right, but that rejection hurts. I’ve experienced that rejection a lot.

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?

The situation right now with COVID-19 is crazy. Most of us are working from home and have been for a year, while some are slowly returning to work. I think the whole work-at-home / work-from-an-office situation will be incredibly strange and stressful for the next year at least. Leaders have to be hyper-aware of that and the stress people are facing. I think many people are flat-out exhausted. You need to give people time off and make sure they take a vacation (even if it’s a staycation in their homes!) You need to remind employees that you care, even small gestures (like sending everyone a box of cookies) can go a long way. Just make sure you’re really listening and when you see trouble, do something about it. Don’t wait.

What would you advise other business leaders to do in order to build trust, credibility, and Authority in their industry?

Write. Write. And then write some more. Honestly, it saddens me a bit to see writing become a less-than-valued skill in many organizations. Now everything is a video. Clubhouse is exploding onto the scene, and everyone wants to jump into live audio calls. I’m not suggesting video or platforms like TikTok, or podcasts aren’t great mediums for building brand and marketing, but personally, I enjoy the written word.

Actually, someone once said to me, “the best business card is a published book,” and I would suggest that that’s still true today. So, write a book.

Can you help articulate why doing that is essential today?

For me, writing is less ephemeral than most other forms of content. Blog posts do “disappear” and become hard to find, but the written word, especially when published, has staying power. Lean Analytics was published in 2013 and it’s still being sold today. I still get asked to speak about Lean Analytics at events.

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?

Although Lean Startup methodology (and other similar concepts such as Design Thinking and Jobs to be Done) are fairly popular today, many CEOs and founders still don’t apply their principles effectively. Unfortunately, I still see a lot of startups that don’t really understand their users/customers and aren’t legitimately solving a big enough problem. If that foundation is weak, it doesn’t really matter what else you do — it’ll collapse eventually.

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 burdens you take on as an entrepreneur are immense. When you go out alone, or with a co-founder, there’s no safety net. It’s entirely up to you to figure things out — and a lot of what you have to do is not stuff you have experience with. You may have never setup a company before. Maybe you’ve never managed finances. Or hired people. And so on. CEOs/founders/entrepreneurs have to level up very quickly on a ton of skills that they weren’t necessarily thinking about when they decided to take the plunge. So, the learning curve is incredibly steep. And as your company grows and succeeds, I don’t think the learning curve ever really lessens. It’s rare that you find an entrepreneur that’s “comfortable in their role” and feels completely at ease with how things are going and has complete confidence in their ability to deliver.

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.

Back in 2007–2008, I raised venture capital funding for my company (at the time), Standout Jobs. I had never raised financing before, and I felt incredible. The fundraising process hadn’t been easy (we actually had one venture capital firm pull a term sheet on us), but once we had our funding partners, I was definitely riding a high. The experience itself was incredibly stressful — I had a young son (a couple of months old) who was in the hospital with pneumonia. I remember standing outside the hospital on the phone pitching investors. But again, when it was done and the money was in the bank, it was an awesome feeling. I don’t celebrate fundraising the same way anymore, because it’s very clearly one step in the journey and not a victory on its own. Raising capital is a huge milestone, but it too often is celebrated as an incredible success; but it’s not really success, it’s giving you the time to get to the finish line (or the next fundraising milestone!)

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.

I’ll share another Standout Jobs story. It’s now 2010 and the company is running out of money. We’re still dealing with a recession from the housing crisis, and we know we won’t be able to raise more money. As the CEO it was up to me to figure out what to do. I could have just given up and folded the business. My investors knew they were losing their money, and the team knew our days were numbered. Those were crappy, crappy days. I felt like a complete failure. In the end, we managed to sell the assets of the company and recover some of the investment that went into Standout Jobs. That perseverance served me well, but it took me about 6 years after that experience to want to start another company.

Based on your experience can you tell us what you did to bounce back?

For starters, I didn’t jump back into starting companies again! After Standout Jobs, I did co-found an accelerator, Year One Labs, but there was a lot less pressure in that experience, and our job was to help other entrepreneurs realize their dreams. So it was “entrepreneurship-by-proxy.” After Year One Labs I was still shell shocked and shifted my focus to working with other founders to help them build their businesses, focusing on my love of building software products. I became VP Product at GoInstant and subsequently VP Product at VarageSale. Running product is intense and stressful, but nowhere near as big a mandate as being CEO or founder, and that suited me just fine until I was ready to start another company in 2016.

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.

This is such a tough question…but here goes.

  1. Believe in Yourself. I don’t think you can be an entrepreneur without believing in yourself and having conviction in your ability to be successful. This doesn’t mean you won’t feel like an imposter sometimes (you probably will) but fundamentally I find that successful entrepreneurs are those that simply believe. How do you get belief in yourself? That’s another extremely tough question. But if you don’t have true conviction in your ability, you may find you have more lows than highs.
  2. Keep Your Eye on the Prize. I like to celebrate small victories, but I don’t let them take over. The highs used to be much higher (and perhaps the same goes for the lows.) I focus more on balance now, and the future state of winning. If you land a big deal, celebrate — you deserve it — but then move on. Don’t celebrate too long and don’t get ahead of yourself. Each small victory is one step closer to whatever final outcome you’re looking to achieve.
  3. Talk to People. You’re going to need two types of support teams: (1) those that love you unconditionally but don’t necessarily understand what it’s like to be an entrepreneur; and (2) those that are living what you’re living (or have lived it previously). So, the first group might be family or friends, a partner, a confidant. Find those people you can cry with. They might not understand what you’re going through, but they have big shoulders. The second group is your peer group that are living and breathing similar experiences. Almost every successful CEO I know has a small network (5–10) of other CEOs that they work with. It has to be done in a completely safe space, where everything is completely confidential, and no one judges you. Your peers won’t because they’re living it. Holding things in and not talking about them is going to result in some terrible (and likely frequent) lows.
  4. Check Your Ego. While I strongly believe that entrepreneurs need to have a ton of conviction and confidence, there’s a tipping point where your ego takes over.You start to win, and you think, “I’m unstoppable. Clearly, I’m a genius. I can do no wrong.” I love confidence, but I hate ego. I think most people are self-aware enough to know when their ego is running amok — it’s only a question as to whether or not they’ll check it, come back down to Earth and deal with reality.
  5. Work with the Best. You may have heard the phrase, “Hire smarter than yourself,” which is a great reminder that nobody really wins on their own. The best solo athletes in the world have a fantastic team behind them. Entrepreneurs need the same thing. Hire the best people you can; the people that challenge you; the people that you would jump on a grenade for. And the same holds true with co-founders. Starting a company on your own is pretty lonely. If you can find a great co-founder, you’re in luck. When you’re down, they’ll prop you up. And vice versa. Finding a co-founder is incredibly hard, but when you find the right one it’s amazing. The wrong one will destroy your business.

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?

Resilience for me is optimism. It’s the belief that things will get better. It’s about fighting for that better tomorrow while dealing with the difficulties you may be facing today. I don’t think of resilience as blinding ploughing ahead until you run yourself completely ragged. If something isn’t working — your business isn’t succeeding — there is a point where you have to call it, take your lumps, think about what you’ve learned, and move on. Live to fight another day.

Did you have any experiences growing up that have contributed to building your resiliency? Would you mind sharing a story?

When I was 10 years old, I lost my younger brother to leukemia. He battled with the disease for several years. It was a brutally painful experience (one I’ve written publicly about.) I had to grow up pretty fast after that, and I’m fairly certain a big chunk of my resiliency comes from that experience.

In your opinion, do you tend to keep a positive attitude during difficult situations? What helps you to do so?

If you’re familiar with the expression, “That dog’s bark is worse than its bite,” then you know how I deal with difficult situations. I can rant and rave with the best of them and get extremely frustrated at times and want to “blow things up” and restart. Someone wiser and calmer than me usually gives me the space to rant and then brings me back to reality. My answer to difficult situations is usually, “work harder.” And go for the small wins and the things I can control. I find it easier to remain positive when others are struggling…I have decently large shoulders for people to lean on.

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.

Your team will look to you for guidance. You set the tone. You help define the culture and how you want people to work and operate. If you’re negative it’s going to seep into your company quickly. The fear will start to mount, and people don’t deliver well under fear. I don’t believe in sugarcoating things or lying to employees — they need to know what’s going on, and in fact, I would say transparency wins the day over trying to be overly positive.

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?

“Fix it!” OK, that’s not inspirational at all, but it’s from a Saturday Night Live skit that cracks me up. The guy is talking about various problems that exist in the world and just yells “Fix it!” as the solution to everything. Some of my colleagues at a past company thought that my approach to doing things was pretty similar. I’m OK with that, as long as people understand that I’ll happily roll up my sleeves to “Fix it!” alongside them.

How can our readers further follow you online?

They can find me on Twitter at https://twitter.com/byosko or on LinkedIn at https://linkedin.com/in/byosko. And my company is at https://highlinebeta.com.

This was very inspiring. Thank you so much for the time you spent with this. We wish you continued success and good health!

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