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Ownership through Failures: An Entrepreneur’s Take on Difficult Decisions with Erik Gross (2/3)

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The entrepreneur, business owner, and people manager are faced with difficult decisions as a part of leadership whether it be deciding to abandon a goal or eliminate jobs through a layoff. Erik Gross, our guest this week in episode 268, highlights the importance of learning from our failures while also owning the decisions that led to those failures. Listen closely to the way Erik owned his decision to become a software developer after some very pointed feedback from a friend.

Original Recording Date: 02-17-2024

Erik Gross is a technologist, a consultant, an entrepreneur and founder, and a career coach. If you missed part 1 of Erik’s story, check out Episode 267.

Topics – Advice for the Technology Entrepreneur, Resilience or Blind Optimism, Three Perspectives on Layoffs, Managing People and A Good Manager, Paid to Work in Technology

3:07 – Advice for the Technology Entrepreneur

  • Would Erik’s advice for technology entrepreneurs be the same? He thinks back to former guest Al Elliott’s description of an entrepreneur from Episode 235, emphasizing that the entrepreneur’s initial idea of the solution to a problem may look different than the ultimate solution.
    • Erik says as an entrepreneur he’s had both successes and failures. The form something was in when it became successful or failed was quite different than what Erik had thought in every case.
    • “There’s this thing I learned…over the years…moments when you find out that you’re wrong about something are golden. They are some of the most important moments you can ever have in your life. You find out a few really important things about yourself in that moment.” – Erik Gross
    • In those moments…
      • Do you have the self-respect to admit and realize you were wrong?
      • Identifying what you were wrong about, which could have been affecting your performance for years, presents an opportunity to never do that thing wrong again.
    • The above took Erik years to learn and handle and is how he generally reacts once he gets past the emotion of being wrong about something. In his entrepreneurial work and in his work with people trying to break into tech (via The Tech Academy), Erik coaches others to process these situations in the same way.
    • We know that no one can be right all the time. It’s the way we respond in those situations that helps us grow! Erik calls these moments “growing moments.”
    • Nick would point out two hurdles in these situations:
      • Getting past your ego and questioning your self-worth
      • Motivating yourself to keep going and change what you’re doing or decide to quit
    • Erik would agree and say there are 2 factors at play:
      • “What you say to yourself sticks. When you say positive, self-validating things about you, they have a tendency to stick. But when you say negative things about yourself…maybe you never voiced them out loud but they are inside…those unfortunately stick really, really well. I’ve found it really helpful to recognize that most of those things, they come from outside influences. They come from others’ criticism, others’ attempt to belittle you or cause invalidation or cause uncertainty or worry in your life. And you can grab on to them and hold them, and they start to feel like that’s actually you. But they originally came from outside of you. When you’re a kid, man, the world is your oyster and life is full of brightness and gold and goodness and joy. External influences can beat that out of you, but it never truly goes away.” – Erik Gross, on negative self-talk and its origination
      • When you have been knocked down, it is up to you to choose to stand back up and keep going. Others can help build us up, but the choice and decision to keep going is ours.
      • Erik tells us he’s been knocked down many times and gone through situations of both tremendous challenge and pain. Though he did not always get it right, he did get it right enough to learn something about himself that he says can be a lesson for all of us. We are each tougher and more resilient than the credit we give ourselves for those qualities.
      • We get to choose whether to stand back up when we are knocked down (no matter how badly or to what extent we were knocked down), but do we remember that in the moment? Exercising the choice to stand up more frequently can help us recognize how tough we really are. The toughness is a recognition that we will inevitably fail in different areas, but we can be joyful in having a choice to stand up and the ability to make tomorrow a new day. Erik tells us this is true for him, and he has seen it be true for many others.

7:55 – Resilience or Blind Optimism

  • How can we determine the difference between being resilient and having a blind optimism about pressing forward?
    • Erik says this is a question any of us could ask ourselves, but it is particularly applicable to the entrepreneurial minded individual. Knowing when to pull the plug on something because it is unwise to continue with it is a challenge, and our ego can often get in the way.
    • “Ultimately all you can do is attempt to be as objective as possible in the moment and look at the situation and analyze the two decisions you have in front of you – continue to plow down this road that so far has been kicking my behind or let go of it, abandon that purpose, that goal, and pivot…. Only you can tell and judge what’s going to do the greatest good over the longest period of time. It’s a very personal decision.” – Erik Gross
    • In looking at the above, there are several areas of your life which will be affected regardless of the decision:
      • Personal
      • Family
      • Groups / work
      • To some extent, the impact could be all people in the above categories
    • Erik is suggesting a mental framework here in which we try to strip out the emotion and be honest with ourselves about which of the two options produces the greatest good long term for you, your family, and the groups in which you are involved.
    • This is a decision no one else can make for you and that you must own.
    • Once you make the decision, don’t look back and get stuck in regret. It will destroy you.
    • Erik is not perfect by any means but has had to make decisions like we’re discussing here.

10:10 – Three Perspectives on Layoffs

  • Erik recounts a story from his time running and trying to scale The Tech Academy when he and his co-founder had to execute a layoff impacting several people. That was a very rough decision.
    • “These people that joined you in your mission, leaned into it like you are…and you have to tell like a third of them that you didn’t make it go right to build the business strong enough to be able to afford them and you have to let them go…that is rough. But you’ve got to analyze it objectively. And you pull the band aid off, but you can’t look back in regret on it. Otherwise it was for not, and you will still dwindle afterward because you’re stuck in the loss of what you had to do.” – Erik Gross, a founder’s perspective on executing layoffs
    • Nick says this sounds incredibly hard. There is the decision to reduce your workforce but also deciding by how much and furthermore who will be cut. Most people impacted want to know “why me?”
  • Suppose you’re a manager who is told they must execute a layoff and has no choice in the matter. What is the advice for this person?
    • In this situation Erik would encourage the manager to start inside themselves for clarity on the situation. Handle yourself first.
    • Moving into executing layoffs and exit interviews without assessing your own internal disagreement with the situation will make the situation even worse.
    • “If there’s still any part of you that’s like…‘why are we doing this’…any frustration on it…you’ve got to have your own conversation with your leader and fully resolve that before you just jump into…actually embarking on it or you’ll be doing it insincerely. You’ll be doing it with your own doubts and reservations about the action.” – Erik Gross
    • As for selecting who will be impacted when it comes to layoffs, there are many factors we could discus. Erik would say the front-line manager or leader should know the business need, the projects the team under you are working on, and some idea of what the next 12 – 36 months might look like in your area. From there look at the group of employees and decide which of them will produce the biggest impact in that future time period using a ranking system (even though most of us do not want to judge or be judged). Erik suggests the ranking is something that must be done even if we don’t like it.
    • “You have certain rights as a manager, but you have a responsibility. And that balancing of ultimately the company has to survive, and that’s your responsibility. You can’t get away from that. That’s why you took the job. You didn’t take it to be popular.” – Erik Gross, on the responsibility of the manager
    • Managers should still seek to be kind in what they are doing.
    • After ranking the members of your team based on the metric above, the people who stay should be fairly clear.
    • When it comes to having conversations with people impacted by a layoff, it goes back to understanding the viewpoint of others. Erik mentioned he’s been fired in the past, and it stinks!
      • Erik mentions a couple of instances where the person delivering the message to him about being fired or laid off was kind and gracious. The kind approach helped Erik deal with the unpleasantness of the situation quickly and move on.
      • Other times in his experience Erik has seen these situations handled crassly or cause invalidation. They were not handled with kindness.
      • “You can never go wrong by being kind and nice to other people.” – Erik Gross
  • Suppose you’re the person receiving the news of being laid off…
    • Something applicable related to interview processes and getting job offers came up recently when Erik was giving a talk for students of The Tech Academy and recent graduates.
    • “You have to prepare to be rejected in the interview process.” – Erik Gross
    • When interviewing for jobs, people will likely get more “no” than “yes” answers.
    • “Even in the most ideal work situation, there is always a possibility that something will happen and they’re going to have to let you go.” – Erik Gross, on the reality of layoff always being a possible outcome
    • If you have done a good job at the company you’re forced to leave and can leave proud of the work you did while employed there, it can be of some help.
    • Erik has no advice that would be worth anything if it were trite like “just get over it.” The situation stinks, and there is no denying it.
    • But, Erik feels a caring and compassion for the tech industry
      • Knowledge workers are very valuable according to Erik. We can apply soulless machines and tools (i.e. digital computers) to real human needs and problems to make an impact for good. That impact ends up being greater than the time spent getting to the solution.
      • It takes a special type of mind to be a knowledge worker. It takes someone who is hard working, persevering, and a willing to be wrong to solve difficult problems.
      • We should not lose sight of our value as knowledge workers, especially if we’re let go.
    • It’s ok to be upset, feel bad for a day or two, go take a walk, etc.
      • “But don’t for a moment think that that is you that’s invalid, that you somehow are lesser than…. Surround yourself with really awesome people who see what you really are and demand that you live up to it.” – Erik Gross, on receiving news you have been laid off
      • Erik uses the example of his wife not allowing him to wallow or be in a “funk” for too long after being laid off. She knows his strengths, weaknesses, and how capable he is. If at any point Erik begins to lose belief in his abilities, she will kindly remind him of his capabilities, the expectation that he live up them, and that the current attitude cannot stand. We can all be a friend like this for someone else.
      • Nick would put his wife in the same category. She has always believed.
  • What about the business owner who has to come to terms with the need to execute a layoff?
    • The owner may not be executing the layoffs at the lowest levels, but that person has to start the chain of events to head in that direction.
    • “Here’s the thing. When you decide to start an activity, when you decide to start a group. Whether you’re stating it out loud, or internally, or you’re not even looking at it, the fact is that you’ve made a contract with yourself and with anyone else who chooses to join you on that mission. That contract includes, for me at least, one overriding principle – you as the creator of that activity are 100% responsible for its success or failure…period…end of story…. At the end of the day you own that thing, good or bad.” – Erik Gross
    • Erik says we can ask others to be responsible for the activity’s survival, and the right people might lean in and commit.
    • A business owner must help people understand the decision to execute layoffs belonged solely to them as part of being responsible for the success or failure of the company. This is ownership. There is no abdicating the decision to someone else, blaming someone else, or dodging the responsibility placed on the owner.
      • Even if the economic climate is not good, the business owner is still responsible for the company’s lack of performance or inability to weather that environment.
    • Sometimes reducing the workforce has to be done for the company to survive.
      • Though this is a brutal message to accept, someone had an idea for a business and was brave enough to create it. Without that happening there would not be jobs for people at the company.
      • “I don’t like a management worker divide at all, but having done a lot of entrepreneurial work, it’s the truth. You put yourself out there to build this thing. You’re owning it fully. That means you’re responsible and have the right to cut off parts of it if it isn’t working.” – Erik Gross
    • There are so many things to think about if you’re a would be entrepreneur, business owner, or manager listening!
      • A manager’s department is a microcosm of the same concept we’re talking about with the business owner.

21:12 – Managing People and A Good Manager

  • What made Erik want to gain experience as a people manager?
    • Some of this is the impulse to teach others well. Erik says in reality he has a mixed rate of success as a people manager.
    • Erik has done extremely well as an entrepreneur. But, he knows his strengths and weaknesses and chooses business partners that will compliment him well.
      • As an example, Erik’s business partner Jack is very good at making businesses scalable and implementing policies and procedures.
    • Erik managed people when he was in sunglasses sales and when he was a store manager for a flooring company
      • “At the end of the day what drew me to that is that I get tremendous personal joy from watching someone become more of who they are. I can see a possibility there. I can see this tremendous ability that could be unleashed whether it’s as a salesperson or as an engineer or as a project manager or someone who can achieve consensus in a real divided group…. When someone doesn’t believe that about themselves, but I know it’s true from close interaction with them, it is tremendously gratifying to help them push through that and start to recognize how awesome they really are. And when you do that, as long as you operate within the confines of how the policies and procedures of that company work, then you’re a good manager of people” – Erik Gross, on being a people manager
      • The belief and self-confidence of the people on a manager’s team is what produces forward motion for the goals and objectives of the team (and the overall company).
    • Nick sees this as a form of but not quite the same as being that friend to someone which we discussed earlier. The manager can see capabilities of the people they manage and can help their employees grow and learn to unleash these capabilities.
    • Erik has an odd mix of things he does right now as the co-founder of a school (The Tech Academy) and helps with marketing and curriculum development for it, he works full time for a technology training company, and he spends time doing career coaching and entrepreneurial coaching for technologists.
      • In Erik’s regular full time job he has an amazing manager who is skilled at managing the needs of the business and the long-term career needs of the people under her. Because of this, Erik’s manager makes a big positive difference in his life. The people leader has the opportunity to meet the needs of the business but at the same time help people grow personally and professionally. This creates very loyal employees.
      • Erik has had other types of bosses in his career who were not so great and is very thankful to have a good one. We hope our listeners can work for a great manager for as much of their career possible.

24:48 – Paid to Work in Technology

  • Right now Erik’s public persona is made up of being a technologist, a cloud transformation consultant, technology entrepreneur, and founder of a coding school.

  • Erik was not professionally paid as a software developer until 2011.

    • Since Erik was 11 years old, he has been writing code and working with technology.
    • As a teenager, Erik would write code on Texas Instruments calculators (specifically the TI-84 model) to create games and for school exercises.
      • Erik would write programs independently of this to use for character development in the game Dungeons and Dragons.
    • In the Navy, Erik was not specifically programming, but he gained some very helpful experience.
      • The Navy had to equip people like Erik to go out into a fleet of ships which could have an array of technologies onboard. And no one knew which flavor or combination of technology they would encounter because the ships were built at different times. Ships could range from being deployed in the last 6 months to being as much as 40 years old.
      • The Navy had to prepare people for anything. This meant a deep dive into digital circuitry, components that make up CPUs and computer memory, how digital storage works, how to build logic gates, details of silicon, how to build an instruction set on a chip, binary numbers, etc. It was extremely deep.
      • Erik ended up on a ship commissioned in 1956, which had no computer stuff on it.
    • After the Navy Erik went into sales, but with 1996 came demand for eCommerce.
      • Erik’s business partners at the sunglasses company suggested the company needed a website.
      • Erik recounts visiting a large tent outside a shopping mall with books that had not sold when they were in retail stores. He bought 8-10 technology books for extremely cheap and learned HTML, CSS, JavaScript, and Visual Basic. Erik built the company’s first eCommerce site.
      • Erik loved working with and learning the technologies but was off selling sunglasses.
    • In the early 2000s Erik was a salesman for a flooring company, and there was a very complex software used to manage the company’s financial operations (booking jobs, doing flooring installs, billing customers, etc.).
      • The company was the 20th largest flooring company in the country at the time and had specific software needs.
      • The company needed to upgrade to the latest version of the software they were going to use, and Erik recognized how complex and difficult it would be. At this point he made it know that he knew about technology.
      • Erik got looped into the implementation and customization of the updated systems, and he loved it.
      • “I really do love this. But I’m in sales. I’m in sales.” – Erik Gross, on his thoughts after being involved with a large software upgrade at the flooring company

  • “At each sort of job or chapter in my life, technology would come creeping in, but the actual shift happened at a very low point in my life.” – Erik Gross, recounting the years 2008 – 2010 when he was not doing well financially

    • In addition to not doing well financially, Erik was also not doing well at home. It was causing a great deal of stress.
    • It finally came to the point where a friend of Erik’s confronted him about the situation in a private setting. This friend said it was not ok that Erik was not making a lot of money and was very firm in the tone and delivery of this message.
    • Erik understood this friend was right, knowing he was letting people around him down as well as himself. In fact, thinking about this consumed Erik for several days. He continued to think about it.
    • Erik recalls being in the car with his friend Jack (who would later co-found The Tech Academy with Erik). Jack asked about his background and if Erik knew things that had potential to make a lot of money.
    • Erik started talking about technology and computers when recounting his background.
      • “Wait a minute. You’ve been programming since you were 11. You did all this computer nerdy stuff in the Navy. Why aren’t you doing this?” – Jack, Erik’s friend who would later become a co-founder and business partner
      • Jack told Erik he was going to connect him with a friend who worked in technology.
      • Erik got on the phone with the friend of Jack’s and was asked all sorts of questions about what he knew.
      • “Erik, you don’t need to go do a degree. You just need to learn how software is being made now. What are the current technologies? That’s all…. I can give you the kind of things you need to learn. I can write it down for you. And if you’re willing to burn the midnight oil and just rip through this and get up to speed on how software’s being made right now, I can try to get you in on a contract I have with the state…. It’s going to be really rough, but if you’ll do that, I’ll go to bat for you.” – Advice for Erik from friend of Jack’s who worked in tech
    • Erik went home and told his wife about the conversation and how much work it would take him to get up to speed, seeking her support if he chose to do it. He told her about the earning potential of putting in the work and how much he loved the discipline of computers.
      • Erik’s wife agreed she would support him.
      • Erik bought a cheap computer on CraigsList and a number of technology books from Goodwill.
      • He would stay up until the early morning day after day to learn the fundamentals of object-oriented programming, understanding databases, revisiting languages he had used and how they had changed, and learning about new programming languages like C#.
      • “Two and a half weeks into this that moment happens like it happened on the submarine, and it all clicks…. And I wrote up a resume and sent it out, and one week later I had a job for $84,000 a year. I had been making $38,000 a year or less. My life changed on a dime. It was that come to Jesus moment of a friend sitting down and saying ‘this is not ok.’” – Erik Gross, on technology becoming a professional activity
      • The tools Erik needed were there the whole time. He just had to realize it for himself.
      • Erik loves the tech industry and has done very well in it to this point.
    • Nick loves the fact that Erik decided to take action based on a friend’s feedback. It’s never a bad idea to share your background and skillset in a specific area with someone else and getting some guidance from others in the same industry on how to improve or fully pivot into a new area.

  • If you would like to follow up with Erik on this discussion, you can contact him using one of the following links:

    • Career Architect – helping technology entrepreneurs launch and scale knowledge-based businesses without risky investments and years of trial and error, using an engineering-based approach to design, testing, launch and growth.
    • The Tech Academy – a licensed trade school which helps people transition to careers in technology through delivery of online and in-person coding boot camps

Mentioned in the Outro

  • Nick was particularly struck by the mention of “being that friend” to others in this interview.
    • Being that friend involves holding someone else accountable for living up to their potential in a kind way. It’s making the other person own the action to do something about the situation.
    • People did this for Erik because they cared about him enough to do it.
    • Though not stated in the episode, Nick would classify this as mentorship. A mentor can hold us accountable in a kind way, make us own our actions, not let us off the hook, and not let us make excuses. A coach can do this too, but Nick immediately thought of a mentor’s role.
  • We discussed decisions and the analysis of the impact of those decisions.
    • This is especially important for an entrepreneur. It could mean abandoning a goal or shutting down a business.
    • A consistent pattern in former guests looking at job changes or other major life changes was the importance of getting input from their families before making a decision. This is a way of seeking support for a decision we want to make which could / will impact the rest of our family.
  • Kindness really does matter.

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