Old Man and the Sea and the Sharks of the Startup World

I find inspiration for sales and leadership outside of most business books. Don’t get me wrong, I have an extensive list of great business books that have influenced me over the years but if you don’t balance it out with novels or biographies, you can miss a more wholistic perspective to understand business and most importantly, yourself even deeper.

My latest inspiration came from The Old Man and the Sea. I read this back in college when I was feverishly studying Hemingway’s writing style for my journalism classes at the University of Illinois, Urbana-Champaign. More specifically, how he uses few words, yet each word carries a power to make the reader complete the thought and how that same approach is game changing for journalism. After recently re-reading Old Man, it offered up an entirely new perspective on where my life is at today; specifically, how the book relates to startup businesses. There were several themes that stood out, but the ones that resonated are as follows:

Resistance to Defeat

As a fisherman who hasn’t caught anything for the last 84 days, the Old Man is fighting against defeat. He never gives in. Instead, he sails further into the ocean than ever before, hoping to land a fish. He finds the largest fish he’s ever seen, hooks the marlin and for three days / nights, despite immense physical pain and mental exhaustion, he continues to push. Then, after finally killing the marlin, the Old Man fights off the sharks even though the battle against them seems hopeless.

“But man isn’t made for defeat. A man can be destroyed but not defeated.”

In other words, victory over the inevitable is not what defines us. Rather, it is our struggle against the inevitable, even when we know it is, that defines us. The more difficult the struggle, the more worthy the opponent, the more you can define your strength to persevere and ultimately, your identity.

Pride, Respect and Mastery

Pride is often depicted as a negative attribute that causes people to reach too far and as highlighted in another terrific book not about business Sway, can lead to people making irrational decisions to save their own pride. In Old Man and the Sea, Pride acts like a prime motivator. After killing the first shark that was eating his marlin, the Old Man wonders if the sin of pride was responsible for the shark attack because it caused him to go out further in the ocean, beyond the usual boundaries that fisherman observe. It was pride in his diminishing reputation that caused him to go alone to prove himself as a great fisherman once again.

The Old Man’s pride is portrayed as the single motivating force that spurs him to greatness. It is his pride that pushes him to survive three grueling days at sea, battling the marlin and then the sharks, and finally it’s his pride that pushes him to return alive with the carcass of the marlin intact to display his accomplishment to his peers.

When relating to the greatness his hero Joe DiMaggio show on mastering the craft of baseball, the Old Man draws parallels to his own craft of fishing and if he can be offer the same dominence to fishing as Joe D has on baseball. In addition, the Old Man relates to the pain that Joe D has with bone spurs to his ailing hands as he fights cramping from holding the line for so long.

Finally, there’s a respect the Old Man shows nature, the marlin during the 3-day fight, and the ocean itself. The old man doesn’t see the marlin as just an advisary that had the potential to outlast him but as a friend. The Old man shows a deep admiration for the marlin and hints that the law of nature is what unites us as humans.

“Come on and kill me. I do not care who kills who.”

When you push the boundaries, go out further than anyone else has, find your marlin and finally after a tireless battle, the sharks pick your marlin apart, only for you to outlast and defeat all of them in the process, this is the biggest parallel that I draw in building, scaling and winning as a startup. Is it crazy? Yep. Is it pride that drives us? Could be. The mantra of anything worth doing will always be difficult and as you face its challenges hold true. Because in the actual overcoming of these challenges is what truly defines us our character and continues to test our strength so that you can look back at your story and say with pride:

“I did that.”

Then you say.

“What’s next?”

“Every day is a new day. It is better to be lucky. But I would rather be exact. Then when luck comes you are ready.”

The Wisdom of the Dog Whisperer and Sales Leadership


Having a Golden Retriever and two kids, I naturally watch a lot of dog training shows. 🙂 Dog training shows can teach you a ton about parenting and leadership. Before you think I’m completely degrading my kids or employees, there are a ton of great examples of how Cesar Millan ‘s lessons in “The Dog Whisperer” can translate peaks to being a great leader. It’s about the importance of rewarding the right behavior and the discipline of good habits. The most important factor in these rules is being consistent with the rules.

If you are not consistent with the rules, (i.e. when the same behavior is sometimes rewarded and sometimes punished) the dog becomes stressed, confused, and starts to take no commands at all.

I’ve seen this dynamic more often than not with sales managers. It’s very common in new managers but it’s very concerning when you see it in a VP of Sales – how long have you been leading this way and how did you get to this position?

An example of this would be celebrating the deal more than the process of getting a deal closed. Closing a deal is the result of the fuel you put in every day, the prospecting, the check in calls, the nurturing angles, the business cases, the art of a good proposal, the buyer call, and more importantly – the “pick yourself up, dust off and do it again” side of sales. In fact, the best sales people make losing look like winning because they did everything necessary to close the deal, but instead of closing the deal they found a way to get a win in other areas. If you pay attention to this process, the little wins during the process and celebrate the execution of it, the more deals will come – that’s predictable success. Most importantly, this practice focuses on all of the finger prints needed to close a deal, learn how you won / why you lost and makes you adapt for the next set.

If everyone on the team feels like they had a successful day and accomplished something, then they are more inspired to to do it again the next day. Setting the right expectation on a daily basis will help your folks understand whether their day was a success or not.

As an example for front end sales:

Did you send out 20 emails, connect with 10 people, write two new posts within your LinkedIn groups that are knowledgeable, share 3 times and comment twice on twitter posts from your network in a positive way and end the day with a clear definition of what the plan to achieve your ultimate goal the next day.

Sales is unpredictable, but this is predictable – if you do it every day than you can predict success. Create the right habits and do them every day, this will lead to success.

If sales folks aren’t putting in the effort on a daily basis to fuel and influence their pipe, then you have to either look at yourself to figure out whether you acknowledge the fuel in the first place or, if you do, tell the person who isn’t putting in the effort what’s expected – if they don’t perform the basics they will never master the art of sales.

If done well, you will lead a culture of predictable success but if done poorly and celebrate the deals that didn’t follow any process or rhyme, you run the risk of dismantling everything at the expense of celebrating a victory. If you don’t know what led to the success than how can you expect to repeat it?

We’re no different than dogs, we like routine, structure and direction which will open up what is possible within every sales person. Set the tone that success starts and ends with consistency. If every day’s success weighs on whether or not deals are coming through than your team will only be focused on pressure tactics to close business (the wrong way) as opposed to nurturing, challenging and selling solutions (the right way). If everyone is anxious about the consequences of not closing a deal every day, they won’t pay attention to what actually closes business – the process.

How Poverty can teach Resiliency

I’ve been running the same run since I moved back to San Francisco in 2015. There have been variations in the route, longer and shorter distances but the main route to the waterfall right underneath the Park Presidio and back has been the mainstay, the core of the run. I reflected during a most recent run how my life has evolved during each run. The original runs with my Golden Retriever (Jinx), the next set of runs with my oldest (Addie) learning how to ride her bike, with my youngest (Audra) reading books loudly in the stroller, with both my kids on bikes and me frantically trying to keep up, and now ones with my new puppy (Soda) who only runs in certain weather conditions. When I’m solo, I think a lot during my runs, and it’s truly a helpful release. Today I thought about my most recent experience, visiting Kenya.

I joined Sama (then Samasource) during the pandemic, so in office visits were not a thing let alone hopping on a plane to East Africa. After working almost 2 yrs at a company, I finally visited our offices in Kenya and saw first hand the impact Sama makes. I speak constantly to customers on the importance of data accuracy in models, how a dedicated workforce is essential for scaling and how you can do all of this in an ethical way, but seeing the work first hand was eye opening on so many levels. To connect the world’s most innovative Computer Vision work that’s happening all around us today with meaningful, digital work with people in the slums of East Africa is quite the mental model to jump through. Yet it exists! Every time you put on a Oculus to experience Virtual Reality, use social media filters on Instagram using Augmented Reality, are exposed to Smart Robots that are revolutionizing farming or vacuuming your floors, or Autonomous vehicles that are just starting to ride driverless, you’re experiencing the work product from people that have been, in Sama’s case, provided a unique opportunity to transform themselves by getting meaningful work in communities where opportunities are not as plentiful. I knew when I visited Kenya I would gain more context on this perspective, but I wasn’t ready for the perspective I actually experienced.

Walking down a mud road during my visit to Kibera neighborhood

One of the first things that altered my perspective was that Sama is a massive company! So many people work on amazing projects for our customers. I had gotten caught up in my own expanding bubble of close to 200 folks that make up the US / EU team, I wasn’t ready to see thousands of people getting to work because of the business our clients give us. Incredibly fulfilling to see this first hand, our customer’s data on screens being annotated. It made me feel connected in a different way to folks that share such a different story than my own that live across the globe but are somehow connected in the same journey together. Powerful.

Movie theater in Kibera

I took a tour of Kibera, Kenya, (the largest slum in Africa and largest neighborhood in Nairobi) where Sama sources the majority of our workforce, and what I experienced was much different than I thought I’d experience. I saw poverty, no doubt, but it was different from the poverty I’ve been exposed to in the US. There was an infectious vibe to this community and an incredible resourcefulness that was inspiring. There wasn’t any evidence of drug use or depression but instead, everyone had an incredibly positive outlook and were thankful for any gains they’ve received. When people heard I worked at Sama, I instantly felt the gratitude in return and it was completely genuine.They had an entrepreneurial spirit to them that inspired me to employ a similar perspective in my own life, and I’m a pretty positive spirit. 

I was wrong about the level of impact Sama makes. I was under the impression that when Sama “Gives Work”, it’s lifting / rescuing individuals out of the slum and putting them into a lifestyle I’m more familiar with. Yet the more I asked, the more I gained a perspective that in providing Digital Work above living wage, this allowed young individuals to make a difference in their own community. They referenced the old generation in their community being lazy and not seizing the opportunities to make their community thrive, but with digital work that we provide, this new generation is investing back into their community and making it better. When giving someone opportunity, it’s essentially giving them the consistency to live they way they want, and what I witnessed was that these people chose to invest in their community. Instead of moving away from poverty, these incredible individuals are instead seeking to improve living conditions, roads, water, electricity along with their families living conditions within the community.

Kibera is called “chocolate” city because of the mud and the rusted tin roofs

So when I reflected on this during my last run, I thought about a company’s own “runs” through different economic conditions, and in Sama’s case: non-profit to for-profit, Series A to Series B, B Corp certification, a pandemic that forced us to adopt a new WFH model and actually house people in luxurious hotels. The run is the mission and if the mission is strong enough, the central route shouldn’t change even though there will be obstacles that force you to weave toward the destination. Yet the main lesson I gained was by Giving Work, you provide individuals in communities limitless options on how to make their own footprint, their own impact. Isn’t that the entire point of living? To make your difference how you choose? To make your footprint in the areas you want to be remembered. 

Inspiring to think of what my home town of San Francisco could be if everyone adopted the same mentality as the people who live in Kibera. Giving work unlocks opportunity, which in turn can make a community thrive, but that’s your choice as an individual as to what impact you make, where your footprint stands and who you impact along your own journey.

The Tech Industry Has a Responsibility to Do More Than Just “Move Fast and Break Things”

The tech industry, more specifically the AI space, has been thrust into the spotlight once again.  Companies are being held accountable for making short-term decisions that make a long-standing impact… and it’s about time.

The companies that push their “ghost workers” or “crowd” to standardize their annotated data that drives down cost and increases speed of delivery finally being exposed on causing irreversible damage on influencing bias in algorithms in favor of profits. The same companies have recently been exposed for other unethical practices such as asking the same “ghost workers” to describe their skin tone in the job application process, thinking that by weeding out certain applicants because of their skin color will help in ensuring they’re not biased in their annotation.

Why have these practices even existed in the first place? I think it can be explained by the mantras that dominate the tech industry itself. We’re taught to “move fast and break things” and while that is great for innovation, translating this into business decisions doesn’t always equate to doing what’s right for society.

You don’t need to be the CEO to have your company’s values guide you to the right decision in difficult situations. The importance that values have as an organization is not simply to attract talent to work for you or inspire people to work harder but rather to guide employees and businesses themselves when facing difficult decisions. These decisions aren’t just what guide leaders of organizations but ones that individuals are facing every day in their work life.

Short Term Sacrifice, Long Term Impact

While AI is pioneering the future, businesses have long faced difficult decisions, as doing the right thing for society can often come at a sacrifice to profits. There are inspirational examples of businesses that were faced with making difficult business decisions that ended up being good for society. In hindsight these decisions seem like a no-brainer but in the moment, they were certainly anything but simple as they were bad for business.

One example of this came in 1982 when Johnson & Johnson’s worst nightmare became a reality. Seven people died in Chicago after taking Extra Strength Tylenol, their best selling product, that was laced with cyanide through tampering. Most predicted that Tylenol would never recover from the sabotage, yet it became a hero moment for the company. The decision as to what to do was placed on the company’s chairman, James Burke, who quickly decided to pull the product from not just the shelves of the Chicago stores where the tampering occurred but the entire product line of 31 million bottles. Those Tylenol capsules that were pulled were replaced with another product in the safer tablet form free of charge. At this time, recalling products was unheard of and this one cost J&J more than $100M and a few years later another $25M with the relaunch of safer Tylenol non-tampering bottles.

The move turned out to be the right one. The stock was teetering in the short term during the recall but quickly steadied and recovered two months later to record highs. The stock has paid out investors in dividends ever since. The interesting part of this entire story was when faced with this difficult decision, James Burke was calm and steady in his decision making. When asked how Burke seemed so in control of the decision at the time, he simply stated that the J&J Credo provided his guiding light.

The Credo, which is nearly 350 words, lays out the guiding light in the first sentence: “We believe our first responsibility is to the patients, doctors and nurses, to mothers and fathers and all others who use our products and services”.

When faced with difficult moments, the values of the company provide the lighthouse to where to steer the ship.

Saving the Soul of AI

The long road isn’t often celebrated in tech, where you’re constantly pushed for instant ROI without a discussion of downstream consequences. But these are exactly the discussions we should be having, especially in AI. We’re finally beginning to hear the world’s best brands begin to detach themselves from the AI tools that source from the “crowd”, but frankly, it’s long past due and the voices aren’t loud enough to make a significant difference.

From my conversations with Data Scientists, they overwhelmingly believe that ethics, fairness and bias in AI are real problems that can be solved today before we go down an irreversible path. There are brilliant researchers who often root against the success of their own research until they’re confident that businesses will make the right decisions. This harkens back to 1941, where researchers retracted papers they submitted to Physical Review on plutonium, holding them until the end of World War II. Do we have to wait for AI’s Hiroshima moment or can we take pre-emptive steps?

There are many facets of doing the right thing in AI, but regardless of industry, it starts with the data supply chain: from data sourcing, to data annotation to data enrichment and management. AI is not yet fully regulated and doing this rigorous work can be hard and go unnoticed. Still, the regulation of artificial intelligence is coming. The short cuts businesses tmake when deciding how their AI supply chain is sourced will catch up to and cost more in the long run, and rightfully so. To pre-empt businesses from making the wrong decision in these moments we need to continually force the conversation, demand that innovation does not have to come at the detriment to humanity and have consequences for those that are not centered on this.

Why I Work at Sama

One of the many reasons why I chose to work at Sama, one of the only B-Corp certified companies in AI, is the strong foundation built on integrity, humanity and the importance of diversity at all levels. These values have guided us through many difficult times, helping us ensure we do the right thing whether that’s taking care of our data labelers during COVID-19 times, or how we approach building the world’s most trusted human in the loop annotation tool that leverages the diversity of our labelers. We’re constantly tested as a business and while it’s tempting to take the short cut it’s typically true that the right thing to do is to stand by our core values regardless of the cost.

At Sama, we believe the right decision for your data supply chain should start with partnering with companies that have a technology-enabled impact story that increases economic opportunity in underserved communities rather than crunches it through margin. To keep us honest, there was a randomized controlled trial through MIT researchers over 3 years, to measure exactly that: Whether a flourishing business can also deliver significant, measurable impact and stand for ethics in AI.

I work at Sama to continually be a part of something bigger that creates growth the right way, because doing the right thing should always be celebrated over short-term, ruthless business decisions. You can be a part of saving AI’s soul and still run an amazing tech business.

Why do you choose to work where you work?

June 30th, 2020, a Milestone

Today marks a milestone for a lot of business leaders and professionals out there. This is the end of the month, your quarter and the first half of 2020 in the bag.

At the end of today, look back and reflect on everything you’ve done this year. Whether you hit your targets, took on new projects, landed a job or laid off from a job, it’s healthy to reflect on the fight you went through. You’ve been tested. You’ve questioned your strengths. Your outlook on race in world has been influenced. You’ve been scared for your family and friends. The uncertainly as to what’s ahead has proven to be quite cloudy and that can be rattling. Despite all of this, you’ve pushed through and survived. You’ve turned challenges into opportunities and become more aware of the issues surrounding you.

Now the question really becomes whether you’ve made a difference, become stronger, led others through the uncertainty and picked them up, helped them through the same mess to see a world in a new light. Success during the next 6 months will look differently than the last 6. The next 6 months will be about how you are even stronger than the last 6 months. It’s no longer just about surviving but turning the world around to be better than it was entering 2020. You may think that your voice is small, but the world needs leadership right now in every corner of life. This adds up to make a compound difference. 

To get this all started, take a few minutes and recognize those who helped you, fought by your side and thank them. Thank your family / friends for being there when it mattered most and kept their confidence in you through everything. 

Thanking them publicly is even more impactful so I’d love to start. I’m not going to include why I’m thanking them, I just want them to know that they made a difference. Carolyn Betts, Sam Jacobs, Sonny McCall, Brooke Motta, Nate Gentner,  Kris Taylor, Chris Monberg, Katrina Wong, David Yandel, Jeff Gore, Mehul Patel, Ed Schafer, Jeff Torbeck, Ronny Criss, Andy Madden. 

One exception on not including reasons is my wife, Julie Yandel. Who’s been my lighthouse and will continue to be my partner in navigating the world in front of us, whether it’s through a storm or sunny weather, we got this. 

After reflecting yourself, please comment below on people that have made a difference in your life this past six months. 

The Perfect Prospecting List

In sales, there’s this promise of the secret list. The one made of gold. The destination is so alluring for the sales person. The list that is filled with buyers who are ready to answer an email with “hell yes!” and pick up the phone ready to see your product with pockets full of money. Best of all? They’re the decision maker and don’t need any buy in from other parties. I have the map that can lead you to this destination. 

The map is nowhere. Neither is the destination. Every sales person will always complain about lead quality, it’s natural. However, those that come around to the fact that the “gold in them thar leads” is the journey itself, are the ones who separate from the pack to become great. When getting a fresh batch of leads, whether you’re an Enterprise AE being handed a lead from your SDR, or whether you are an SDR getting a batch of leads from your RevOps person, here are some good reminders to get you going: 

  • Look at your leads with the intent to screen in, not screen out. Spend the extra time to “connect the dots”. 
  • Look at the company, not just the user and ask whether or not the company could use your solution and what the user may stand to benefit from passing you on internally. 
  • Turn a loss (”no” on an email or call) into a potential win by asking the extra question on how you can help the prospect in other ways than selling them something. Maybe it’s an introduction to someone in your network that could help, or a recommendation on where they can take their kids hiking this weekend. Always look to add value. 
  • Research the user, not just the company. Find common connectors within your organization as well as your network to “connect the dots” on making the introduction warm. 
  • Research the company, not just the user. Find connective value to other companies within a similar industry. Is there a trend happening in this industry that you can spot early to “connect the dots” and create a compound effect in sourcing. 

Finally, always…. Always stay positive during the hunt and discovery process. It’s tough to push through but if you go the extra mile every day, you’ll turn 10 leads into 100 just by peeling back the extra layer that most don’t bother with. 

How this ‘Moment’ will forever brand you

I was interviewed a few weeks before Covid-19 became a pandemic. The topic was “Keep you Hiring Funnel Overflowing in 2020 & Beyond” and I broke up a few of the major themes from the podcast into separate posts to elaborate even more. What I’m trying to center on is whether, in the matter of only a month, the content aged poorly in a matter of 45 days. More importantly, do the themes apply to today’s current landscape. Let’s take a look at some of the themes and see how many (if at all) apply to the current Covid-19 world.

Why a Network First Mindset Always Wins

This theme focused on how you should always seek to be of value to your network. With time and consistency, your network will start to do the same in return. In the podcast, the concept focused on ensuring you find appropriate connections of value within your network at all times so that you make new connections in return that will help you get introduced to the right candidates.

How this applies to the current Covid-19 World:

If there’s one thing to focus on right now it is just this concept. Ensuring everyone within your inner network is met with an opportunity for you to present value is more crucial than ever before. I’ve seen countless people extend themselves and their business offerings in this time of need without any reciprocity. I’ve also seen the opposite, where some people are seeking to take advantage of the current state and promote their needs without offering much in return.

If there’s any silver lining to this pandemic it’s shown how much closer we can become while we become further, physically, apart. Going through the same chaos has, in turn, brought us closer together and truly shown the human spirit is resilient. It’s also shown the need to be connected to one another and how a network-first mindset is really the only appropriate one in light of everything that’s going on.


This theme focused on how a company’s brand is truly important in attracting the right people. When you pop on a website and you’re inundated with demo requests, pop-ups, forms to fill out and screen takeovers before you can actually consume the content or what the company is about, you’re hit over the head with a “used car lot” experience. It says that before presenting you with anything, you’re asked to jump into their sales funnel to make a purchasing decision.

How this applies to the current Covid-19 World:

Who you are as a business and what you value is on full blast right now. Companies pivoting their business models to respond to the current pandemic shows everyone what your values truly are. There are other businesses that are forced to make tough decisions like lay-offs and furloughs, which puts even more people in difficult situations. The important point here is not what you have to do but how you do it. It matters if you make your employees feel like humans and not numbers as you lay them off, take the time to understand that this time will pass and when it does, your actions as a company will come to light. I’m not saying that companies are inherently evil if they have to lay people off, I understand that this is the reality of the world today, but if you treat your people like they’re expendable and without heart, this will certainly bite back when you need them again.


This theme focused on two things:

  1. How depending on referrals does not equal to a diverse and multifaceted team.
  2. Look for potential in your candidates rather than if they’ve done the same thing in the past.

Diversity is incredibly valuable in understanding different ways to tackle problems. Any team that has their identity firmly rooted in many perspectives will outperform those with only a few. Don’t just focus on race and gender but also personality types as well. The other added benefit is that a diverse culture will offer multiple perspectives and end up improving every team member’s growth both personally and professionally. This creates a loyal team that bands together through good times and tough ones.

Hiring for potential over experience is a personal mantra of mine. It’s harder on the interviewer to look for signs of potential outcomes than actual outcomes but I’m telling you, this pays off in the long haul. I’m not saying hire an entry-level salesperson to take on an Enterprise AE role, but I am saying that don’t limit yourself as a hiring authority that focuses on industry, role, and experience exclusively for your hire. As an example, if you’re looking for an Enterprise AE in MarTech, try opening up the search to candidates that come from a different, but similar industry with experience as an Enterprise AE. The reason is simple, if you give someone a chance, they will outperform your safe decisions and if you only stick with safe decisions your competition will lap you.

How this applies to the current Covid-19 World:

Look, there are more candidates on the market today than there were when I did this podcast and surely, many of them have some incredible experience to do the job. In this time they will perform, but I question how long they will be interested in doing the same thing they’ve been doing for years when the economy bounces back and more options start to resurface.

Final thoughts:

I was unsure of the outcome of the exercise when I started this post, but in writing this, it becomes obvious that staying true to your principles can guide you through the toughest of times. Your values are your compass when it seems you’re lost in a dark forest without a glimmer of light showing you the way out. How do we get through this together? Stay connected, focused on improving yourself as well as others and solidify your brand in the process. We’re in a moment of time but how you act during this time will define you when we get through it.