Aviv Ben-Yosef: “I think founders have to stop depleting their people’s trust”

…Another aspect that’s immensely useful for highly successful startups is to make innovation a regular occurrence. Working with clients, I’ve helped implement processes and frameworks that make your bright team actually invest time in trying to come up with novel approaches instead of always following orders and doing what’s on their to-do list. Startups have such […]

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…Another aspect that’s immensely useful for highly successful startups is to make innovation a regular occurrence. Working with clients, I’ve helped implement processes and frameworks that make your bright team actually invest time in trying to come up with novel approaches instead of always following orders and doing what’s on their to-do list.


Startups have such a glamorous reputation. Companies like Facebook, Instagram, Youtube, Uber, and Airbnb once started as scrappy startups with huge dreams and huge obstacles.

Yet we of course know that most startups don’t end up as success stories. What does a founder or a founding team need to know to create a highly successful startup?

In this series, called “Five Things You Need To Create A Highly Successful Startup” we are talking to experienced and successful founders and business leaders who can share stories from their experience about what it takes to create a highly successful startup.

I had the pleasure of interviewing Aviv Ben-Yosef.

Aviv Ben-Yosef is an advisor, coach, consultant for tech executives and leaders, and the author of the recently published The Tech Executive Operating System. In his consulting business, he helps companies worldwide, ranging from day-old startups to Fortune 100 companies. Aviv’s mission is to help create world-class engineering teams that achieve the unthinkable by upgrading tech from a tool to an active business partner.


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’ve been coding since I was nine years old and have been enamored with the possibilities software creates since then. After working in both tiny startups and enterprise companies, I decided to become independent nine years ago and helped several startups on their roads to successful “exits” and to become unicorns. In the past few years, I’ve transitioned from writing code to helping my clients create R&D teams that are innovation centers, not cost centers.

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

When I worked as a highly paid software freelancer, I got to see the incredible impact that companies got from that help. However, I also noticed that productivity seemed to return to its previous state once I moved on to my next clients, and I hated seeing leaders wasting their time handling “average” teams. That’s when I decided to help companies create remarkable engineering organizations and lower their need of hiring expensive “band-aids” to help with coding, like myself.

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?

When I was just transitioning into consulting, I met my mentor, Alan Weiss, the “Rockstar of consulting.” Having access to his insights and experience provided me with a shortcut to establishing a business that dramatically helped companies worldwide. I recall sitting in one of his events in Palm Beach and realizing that I had a book in me that needed to be written. Less than a year after that, I had already completed the manuscript.

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

Frankly, I think it boils down to having a higher standard for what excellence means in my industry and the chutzpah to push my clients to achieve it. A CTO once told me that all of their meetings, across the board, become dramatically more productive after I sat down with the team and taught them to be less nice to each other.

How have you used your success to bring goodness to the world?

I’m a big believer in providing value and spreading knowledge globally. I wrote The Tech Executive Operating System because I cannot work with all the leaders who need help, but for every word in the book, I’ve published 4–5 times that for free in articles and hours of videos and podcasts. Seeing my online writing reach millions worldwide is a small way to make my industry a bit better.

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?

First, there’s, of course, the Israeli chutzpah, which is vital for providing candid feedback. One time I was working with a local startup that was having some difficulties. As I was interviewing one of the executives, I got a distinct feeling that something was off. I asked him point-blank, “you don’t even want to be here, do you?” That helped him admit the truth — to himself, too — and we could decide on a new path for the company within a couple of weeks.

Second, maintaining a beginner’s mind is fundamental to my work. Yes, having worked with dozens of companies means that I can see patterns emerging. Nevertheless, I always address a new situation with a fresh perspective and curiosity. That is the only way to curb biases and cookie-cutter approaches. For example, when a client tried to implement verbatim an idea I covered in an article, rather than trying to shove a square peg in a round hole, I helped them perform some Socratic questioning and realize what subset of that approach made sense for them and which concepts just weren’t a good fit. Every company and team is different, and we have to create bespoke methods.

Third, when you’re your own boss, you must have great discipline. Only with it was I able to write my book while in lockdown with three young kids and working with my clients — and finish the manuscript more than two months early!

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?

When I started working on my own almost a decade ago, most of my friends and colleagues were unanimous: This is just a phase, the “right” thing for you to do is start a startup company. Many people I value completely dismissed the viability of the work I now do, and in retrospect, I believe this was affecting me for years. I did not mentally go “all in” because I was repeatedly told it would be a mistake. Whenever someone approached me with an offer to join their company (which is still quite often, to this day), I would start questioning all my decisions and plans.

I believe those years weren’t as effective in personal growth as they could have been due to that “advice” I was repeatedly given. About five years ago, I realized that even bright and successful people don’t always know everything. I had to decide what I wanted and haven’t looked back since.

Can you tell us a story about the hard times that you faced when you first started your journey?

I am genuinely lucky and grateful that I always had at least decent business since I started my journey. The struggles have always been around shedding ego and not standing in my own way. For example, being the sole breadwinner for a few years made me very reluctant to spend our hard-earned money. When it came to living a better life that we could afford but were afraid of, and for things like investing back in my business and my development.

Further, I decided to reinvent myself to solve a whole new level of problems. Where initially I’d swoop in and help companies implement new technology rapidly, I realized that I was treating symptoms and not the root causes. Deciding to move into full-blown consulting globally required several iterations and a constant effort to perform such a shift without risking my family’s well-being.

Where did you get the drive to continue even though things were so hard? What strategies or techniques did you use to help overcome those challenges?

I’m a huge believer in setting suitable support systems for ourselves. I found a community of like-minded and bright people and consulted them. That eventually gave me the courage to invest in myself and reach out to a coach. Life’s too short to try and “do it all alone.”

We also can get a real boost from making sure that we make progress every day and celebrate it. I ensure that I progress by having an accountability partner. She and I talk every workday, even though we’re half the world apart. Knowing that I will have to tell her I wasted my time or procrastinated on a challenging task gives me the boost I need to avoid it. And if I fail, she’ll hold me accountable. The other side of the coin is that she can shed a positive light on my progress even when I’m “in the thick of it.” Coupling that with the practical tips from the excellent book Learned Optimism has been instrumental in my work, especially during COVID.

The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. Can you share a few ideas or stories from your experience about how to successfully ride the emotional highs & lows of being a founder”?

Personally, I never had much trouble riding the highs. The lows are a completely different beast for me. I believe that any successful entrepreneur eventually develops some callousness to rejections and setbacks. I find that what works for me, in general, is to generalize success and specify failures. For example, when I see a client undergo a significant transformation, I think to myself, “wow, I’m really good at this.” On the other hand, I treat rejections with, “well, this specific prospect on this specific day failed to realize the value in working together.” You have to treat rejections with incredulity, or you’d drown.

Let’s imagine that a young founder comes to you and asks your advice about whether venture capital or bootstrapping is best for them? What would you advise them? Can you kindly share a few things a founder should look at to determine if fundraising or bootstrapping is the right choice?

I’d start by saying that I believe it is significantly harder to bootstrap B2C products than it is to do so for B2B products. Therefore, I’d recommend founders who want to create the former to look for funding unless they have a really good reason not to do so.

For the rest of the cases, I think that founders should weigh their honest capabilities and where they would be limited. For example, some people do not have the financial wherewithal to bootstrap for months on end, or they would have to bring on external professionals in a way that would make bootstrapping hard. In those scenarios, funding can make the impossible possible. However, if you’re looking to solve a problem where your core team is capable of creating an MVP and marketing it, there’s not a lot that can go wrong with giving it a shot.

Ok super. Here is the main question of our interview. Many startups are not successful, and some are very successful. From your experience or perspective, what are the main factors that distinguish successful startups from unsuccessful ones? What are your “Five Things You Need To Create A Highly Successful Startup”? If you can, please share a story or an example for each.

The first thing that I think is essential is ensuring that many people in the organization possess Product Mastery. It is a term I coined for distinguishing between being fluent in what one does in the company to what the company does. Product mastery means that people have a deep understanding of the customers, the problem your product is solving for them, what is happening in the industry, and so forth. For example, I always tell my clients that if all their software engineers are obsessed with their tech tools or the new shiny programming language they want to use, they’re not likely to spend their brain cycles on the right things. Creating friction between them and the “real world” can create a fertile ground for innovation.

Second, organizations have to orient themselves around impact and results. It is natural as companies grow to gravitate towards a setup composed of silos and broken-down tasks. However, that’s not the best way to achieve your goals. Creating an organization where each person is aware of the impact their work is intended to achieve and providing teams with the autonomy to find the best path to achieve it is where the magic is.

Another aspect that’s immensely useful for highly successful startups is to make innovation a regular occurrence. Working with clients, I’ve helped implement processes and frameworks that make your bright team actually invest time in trying to come up with novel approaches instead of always following orders and doing what’s on their to-do list. A culture that makes space for playing tinkering and innovating must also embrace failures. If the team’s “innovation” never fails or results in a dead-end, they are not genuinely going out of their comfort zones.

As an Israeli, I’ve come to value the effect of chutzpah in organizations and the art of soliciting feedback across all layers of the team. I think the onus is on leadership to teach people to speak their minds and be vocal about their opinions and ideas, especially in cultures where chutzpah might be the norm. As a corporal in the IDF, I spoke up against a senior officer’s idea. Do you know how people responded? They listened to what I had to say and weighed it on its merit. I wasn’t “brave” — it was simply what was expected. Can you imagine what would happen if more cultures were like this?

Finally, I think founders have to stop depleting their people’s trust. Too often, we forget the effect that our words and actions have on our team and that, as leaders, we are effectively always being watched. Everything we do should be seen as if we’re actively modeling the proper behavior to the team. For example, if your company’s values include “work-life balance” and yet the team is put in blitz mode repeatedly, no one’s going to believe any of the other values you put so nicely on the walls.

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?

A mistake I see a lot is what I call premature organization. Given how hard it is to get talented people to join your company, you might be inclined to provide them all sorts of titles and promises. The issue is that these tend to create lopsided org charts where there are a bunch of managers/leaders and not a lot of actual people doing the work. I suggest fighting the urge to over-promise and setting realistic goals with your team. Expectation setting right from the start is crucial to avoid getting too much organizational debt at an early stage.

Another mistake I’ve recently seen happen more often is the tendency to bet too much on people’s potential. That is, I see founders bringing on a lot of first-timers and hoping that they would learn fast enough. I’m a big believer in letting people “rise to the occasion,” but doing so with most of your leaders might just be pushing your luck too much. Also, keep in mind that this personal growth often requires proactive coaching from the founders. Do not overcommit your attention and consider what a healthy ratio of experience and potential for your team is.

Startup founders often work extremely long hours and it’s easy to burn the candle at both ends. What would you recommend to founders about how to best take care of their physical and mental wellness when starting a company?

I’ll start with stating that I know that most founders who’ll read this will just think to themselves, “well, he’s saying nice stuff, but I can’t do that.” Tough luck; they’ll have to learn the hard way. Nevertheless, I have often heard people say that what I get done in two days most people don’t do in a week. That’s because I’ve learned that working shorter but extremely focused days is a lot better. I protect my time adamantly and avoid anything that doesn’t clearly move me towards my goals. When I was the first employee at a startup, we all worked 12-hour days the first month. After almost falling asleep at the wheel on my way back one day, I called it quits. I said that I’m going back to normal hours. Fast forward a week, and the entire team started working sane hours, and you know what? Nothing bad happened. When you know you’re going to be sitting at the office for 12 hours anyway, you lose a sense of urgency, and the quality of your work deteriorates. I’d rather have four focused hours a day than 12 lousy ones.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I would love to find a way to make everyone, youth and adults, simply read more. I believe that reading books and educating ourselves is a personal growth hack that not enough people are using. I’ve taught myself how to code and pushed myself into my preferred career. Providing others the tools to learn by themselves and enjoy all the knowledge others have collected for us in the past is something I hope to be able to focus on one day.

We are blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch, and why? He or she might just see this if we tag them.

Probably Andrea Bocelli, merely because I’m such a big fan. I envy his talents and would love to share a candid conversation.

How can our readers further follow your work online?

Other than grabbing a copy of my new book, The Tech Executive Operating System, I think the best way is to get my newsletter for tech executives, which goes out weekly with articles, podcasts, and exclusive insights: https://avivbenyosef.com/newsletter/

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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