Entrepreneurs have no shortage of ideas. But how do they know if a new business idea is actually a good idea? Our guest this week would advise seeking fast feedback during the ideation process to save time, preserve energy, and remain focused on delivering value to your intended audience.

This week in episode 294 we’re rejoined by Erik Gross to discuss some of the lessons learned from his recent entrepreneurial pursuits. We’ll talk through how the entrepreneur can go from ideation to taking action. This includes generating ideas, capturing ideas, scrutinizing or testing ideas, and deciding to abandon certain ideas. We also discuss how the entrepreneur, business owner, or manager can invest in employees even before they start work by making roles occupiable. And it starts with putting all the pre-requisites in place to write good job descriptions.

Original Recording Date: 09-07-2024

Topics – Entrepreneurs and Ideas, Focus and Subjecting Ideas to Scrutiny, Sources of Feedback, Scaling Business Opportunities with Automation, Entrepreneurial Succession Planning and Attitudes, Investing in People and Making Roles Occupiable, Thoughts on Employee Onboarding, Transferring Duties to Others

2:29 – Entrepreneurs and Ideas

• Erik Gross is a developer, an architect, and an entrepreneur who has been very active in the tech space over the last 10-15 years.
  • This is a return visit for Erik to our show. You can find our previous discussions with him in the following episodes:
    • Episode 267 – A Theme of Learning with Erik Gross (1/3)
    • Episode 268 – Ownership through Failures: An Entrepreneur’s Take on Difficult Decisions with Erik Gross (2/3)
    • Episode 269 – Monetize Yourself: Leveraging Your Most Valuable Knowledge with Erik Gross (3/3)
• Though we did talk about entrepreneurship a little in episode 268, does the entrepreneur naturally get a bunch of ideas to chase, or is there more science behind it?
  • Erik knows many entrepreneurs and says in general the entrepreneur has a plethora of new ideas, and this can be both good and bad.
  • Erik learned the idea itself is less valuable than executing on an idea, but he still gets excited when he gets what seems like a great idea.
  • “If you’re paying attention, if you’re interested in helping people, if you’re interested in starting and growing things…you’ll have lots of ideas. Is it going to withstand a scrutiny from the marketplace? Will people pay for it? Is it something that has legs? There are a lot of other questions. But yeah, the ideas…most entrepreneurs…they are full of something, but generally ideas are what they are full of.” – Erik Gross
• Do most entrepreneurs keep a list of ideas they will go back and reference?
  • Erik, like many technologists, is a nerd for tools. He uses Obsidian to capture ideas.
  • When an idea hits, Erik has been known to pull over if driving to capture the idea and get it out of his head. Otherwise the idea might be lost, which is a terrible feeling.
  • Even if people make lists of ideas, it does not mean they are going to execute on any of them. Periodic review of your ideas is a good practice because something you jotted down a while back may be related to what you are currently doing.
  • Nick says keeping a list of ideas makes sense whether we are an entrepreneur or just a technologist, a people leader, etc. These ideas can be for things we want to study, blog about, research, etc. Where Nick fails is going back to review past ideas.
  • Erik does go back and review past ideas he’s captured (could be for product design, offer design, etc.)…usually about once per month.
    • Often times something will trigger him to go back and look through past ideas.
    • He may have captured a specific tool which could come in handy later, for example.
    • “I’m just deeply curious and interested in a lot of things, and especially in the entrepreneurial space, I have a hard time not thinking about it.” – Erik Gross
    • Erik would tell you he is rarely not working. He might be thinking about how to solve a specific problem or physically doing work.

7:17 – Focus and Subjecting Ideas to Scrutiny

• How does the entrepreneur focus their attention in the right area when they have multiple ideas?
  • “I learned a while ago that when you get that urge to look at a new shiny object…generally, it’s because you think that shiny object is going to fix a problem you’re having executing. But almost always, the plan you put in motion to execute in that area was based on some earlier guidance that at one point you really agreed with. It made sense to you…. Most of the time, its failure to actually get the performance or the results that you wanted is due to your applying it incorrectly.” – Erik Gross
    • Erik says we can go back and look at what we were trying to make work in the first place, review the source material now that we have more experience, and be honest about where we failed to execute.
    • This process usually prevents looking at the shiny object and enables us to apply an engineering mindset to the recipe for success we were trying to follow. How can you go back and correct any mistakes?
  • For those in any creative or engineering space, Erik recommends reading A Technique for Producing Ideas by James Webb Young and says it lays out a mental model for generating ideas that is as reliable as engineering.
    • When Erik discovered the book, it was the first time he had seen that mental model laid out as a process. Erik also realized that he had been using the same mental model for years. Listen to how he describes his own “mental machine.”
  • After generating what seems like a great idea, an entrepreneur has to willingly subject the idea to scrutiny. Putting your idea into the marketplace of ideas or the marketplace of services and products takes some courage and humility.
    • “Be willing to be wrong. Be willing to take sometimes harsh feedback or criticism. It’s so much better to find out very quickly…. That feedback loop, especially in the early processes of an entrepreneurial launch of a product or service, that feedback loop should be hours or days.” – Erik Gross, on how entrepreneurs can think like engineers and use feedback loops
    • Fast feedback may come in the form of being advised not to do something. It would be better to get horrible feedback quickly instead of after months of effort spent building something.
• Does becoming ok with failing fast remove attachment of ego to the idea?
  • Erik says yes and shares the story of working for a company that did 3D modeling around 2010.
  • While working there, Erik got what he thought was a great idea for a pocketbook for devices that could also hold other things.
  • Erik remembers sharing the idea with his management at the software company, and they told him it was not a good idea. While it was demoralizing to Erik, he knows they were right, especially with the change in form factor of mobile devices over time.
  • The experience of subjecting ideas to scrutiny can be humbling, but Erik stresses the importance of doing this very early on.
  • “When you get knocked down, the only person who can pick you up is you. And you have to agree to stay down. You have to agree to it…. It’s fine to get knocked down. Of course, it’s going to happen. It’s fine to feel bad for a little while. What are you going to do a little while later? Are you going to stand back up and jump back in, or are you not? That’s personal responsibility and integrity, and it’s a choice.” – Erik Gross

13:57 – Sources of Feedback

• Where should the entrepreneur seek the fast feedback on an idea?
  • Erik would encourage listeners to check out Joel Erway, creator of The Power Offer.
  • In the online marketing space, we see consistent launches of new products and services.
  • The Power Offer as a framework says you should call out your specific audience, which requires you think deeply about who you want to sell to (i.e. an identity or persona).
    • Erik reminds us that we cannot sell a new product or service to everyone.
  • You’re asking a simple question to your intended audience about their interest in getting a specific benefit without certain obstacles or pain points.
    • Erik says it’s been extremely valuable to ask this type of question and that he’s done it probably 8 different times in the last couple of years.
    • Start with your warm market, which Erik defines as anyone you have the ability to contact right now. This might include social media followers, e-mail subscribers, etc.
    • “Business owners – if I could help you make more money and improve efficiency by leveraging cutting edge AI and automation tools without having to pay for expensive, time-consuming custom applications, would you be interested? …That’s one of the ones that worked. The ones that didn’t work are legion, but thank goodness I found out super fast.” – Erik Gross, an example of how he leveraged the Power Offer
  • Erik reminds us that people do not pay for your product or service. They pay for the benefit it provides.
    • It’s important to specify the audience so people can understand if what you’re offering can benefit them. And if it does, they will pay for it.
    • "It’s just a rapid feedback loop. That’s all it really is. It’s your chance to find out really quickly whether it’s got any legs. And in general, the people in your warm network are often very similar to the kind of people that you want to be working with anyway…. I have tremendous admiration for an entrepreneur, for a business owner who is willing to put themselves out there and try to grow and build something. I speak to them because I am them. " – Erik Gross, on leveraging your warm network to vet ideas
    • Erik is able to identify with the group that a product or service could help. Nick thinks that is important as part of this.
  • If no one expresses interest in your idea, it’s ok because you won’t spend time going and making the thing.
    • Erik says no one will remember that we didn’t make something. He’s tried out several ideas, and only a few of them were met with a lot of interest.
  • “It’s real easy when you come up with what you think is a really good idea to only look at that thing from your viewpoint. To get honestly really emotional about it or attached to it, it’s really really easy. An entrepreneur shouldn’t be concerned with their own viewpoint very much…. They need to consider the viewpoint of their ideal audience their ideal customer…. You are there to serve them. You are there to provide more value than they paid you for, and that’s really hard to figure out how to do if the only point of view about your product or service that you look at is yours….” – Erik Gross
    • In addition to feedback from the intended audience, we need people in our lives who are willing to give us critical feedback without fear of hurt feelings.

20:32 – Scaling Business Opportunities with Automation

• How did the Most Valuable Knowledge Framework as we discussed in Episode 269 come into play as part of Erik’s ideation processes?
  • Erik says this is the earlier stage of ideation and something to help you think through what you could do. You might use Most Valuable Knowledge or some other mechanism to generate ideas.
  • If you’ve generated multiple ideas that you like, then it is time to go and get feedback on them as we’ve discussed.
• How did Erik’s business idea end up landing in the automation space?
  • Erik says this one took longer than some of the other ideas he’s tried to test out in the marketplace.
  • About a year ago he was thinking about the opportunities in the online marketing and coaching space, and Erik stumbled upon Make.com.
    • He bought a lifetime membership, tinkered with it a little for social media content creation, thought it was cool, and then didn’t think about it much.
  • A couple of months ago Erik was working to find business opportunities with more scalability than what he had been doing.
    • Erik kept coming back to the automation space, but it seemed mechanical and kind of boring because the problem he was trying to solve was a little boring.
    • After remembering Erik had signed up for the Make.com platform, he decided to go research how other people were using it. He also found content produced by Liam Ottley on building a business in the AI and automation agency space.
    • “Wasn’t there something I was using or looked at a year ago…that might fit this new sort of area I’m interested in?” – Erik Gross
• Did landing back on the same tool again have anything to do with not executing plans the way Erik wanted?
  • Erik gives the example of his coaching business. He loves the 1-1 interaction with clients but could not figure out how to scale it to a larger operation.
  • Part of the reason Erik is looking at entrepreneurial activities is to find something that can safely replace his 9 to 5 job.
  • If Erik were to become a full-time entrepreneur, in addition to financial stability, the work would need to satisfy his internal purpose to help people (something he loves doing).
  • “I want to see the person that I’m helping and look at them before, during, and after and just watch them expand and grow and do great. Whether that’s career coaching, whether that’s a business owner whose employees suddenly have 30% more of their time for highly valuable skilled knowledge work because of the automation solutions we build for them…I want to see that help. That’s my gratification. And yes, I want to get paid well for it.” – Erik Gross
  • Nick says getting the gratification one is seeking makes us more likely to iterate on an idea to improve it and make it more valuable to the people you’re trying to help – and execute the plan more efficiently.
  • Erik believes we should be working, should be of service to others, and that we should be busy. Erik also works very hard so he can enjoy leisure time.

26:36 – Entrepreneurial Succession Planning and Attitudes

• How can the entrepreneur learn to notice it’s time to take a vacation and allow themselves to do it?
  • Erik has heard about the idea that an entrepreneur cannot take a vacation.
    • “If you have a business that requires you to be in the business, you don’t actually have a business.” – Erik Gross, sharing a strongly worded viewpoint he has heard from other successful people
    • Erik’s take is that each person has a unique level of sustained effort to put toward something.
    • “I’ve worked through that before, and I’ve learned that you actually harm yourself when you do it, and you harm the activity you’re trying to grow. The reason it’s growing is because of your drive, purpose, creative energy. And we can fool ourselves when we’re getting…burnt out, but it isn’t the same as it was when you’re not burned out.” – Erik Gross
    • Erik shares an example with us from his own life. He’s been working very hard for a number of weeks but shares a specific instance where he intentionally chose to take a morning to relax.
  • Suppose you’re an entrepreneur who accepts they are going to reach the point of burnout.
    • Erik stresses the importance of having a strategy for finding the right people you can trust to take on some of your responsibilities.
    • “And if that isn’t part of your initial process of planning this business, then you are really planning to have a much higher pressure second job.” – Erik Gross
    • Maybe you accept that at first a company will be just you, but you need to identify at what point you will bring on more staff, how you will find them, and how to know what they should be allowed to work on.
    • This is also helping to set up the eventual future sale of your company if that’s an outcome you want to consider.
• Nick labels the above as succession planning. Entrepreneurs need to do this as do people managers. Many people want to hoard knowledge and struggle to want to train others or offload responsibilities. What is Erik’s take?
  • Erik has seen attitude this far too often, especially in service-based businesses.
    • It starts when an individual becomes extremely talented in an area like masonry, plumbing, etc. and then wants to grow their business.
  • Erik has observed 2 things that can harm growth.
    • The first is being unable to let go of delivery of the actual product or service, unable to completely trust that someone else will do it. The business owner / expert may truly believe no one else can do as good of a job as they can (due to the pride they find in their work).
    • Some are of the opinion training their people well means the people will leave and become competition. This is the same to Erik as “ideas are worthless. Execution is everything.” Building a person’s experience in service delivery does not mean they automatically know how to run a business. They do not see the pressure to make payroll or understand how to handle the marketing, the referrals, and other administrative tasks. It’s better for the business owner to invest in the people, even if they leave and go into business for themselves.

33:48 – Investing in People and Making Roles Occupiable

• How do you figure out who to invest in whether you’re a business owner, a mentor, or a hiring manager? What are the qualities we should be looking for (keeping in mind our backgrounds are in technology)?
  • This is something Erik and his co-founder Jack really had to work through for The Tech Academy. In the beginning, they did everything. Early on they defined a strategy to help in this area that’s been successful.
  • “Periodically, we would list out…all the things still on our plate. At the beginning it was everything…. We’d list out all the different roles we were fulfilling. And then we would figure out which one of those roles is keeping us from selling and delivering, the pillars of the organization. Because those are things we had strong expertise in and that guaranteed the survival of the company. So we’d look at…what are those things on that list that we’re doing that aren’t actually selling or actually delivering? And there would be a lot of them. Ok, which one would free us up the most?” – Erik Gross, on what he and his co-founder at The Tech Academy would do as part of a strategy
  • At this point people usually go out and start hiring, but Erik suggests there are more steps to do this well.
    • "You have to define the role you want them to do and make that role occupiable….
    • Making a role occupiable means listing out everything that role does, the tools someone in that role would need, and the process used to get tasks completed. The process may be almost habit for you, but you need to be thinking of people who are new to the company / team and would not know this by default. They immediately would have some background and understanding of what to do.
    • Erik says consider any basic orientation outside the person’s role that is needed. If that doesn’t exist, you will need to prepare it.
    • All of the above takes time, and it’s time away from selling and delivering and doing the role in question.
    • “But it’s worth the time to organize it because what will happen is as you define that role, you will start to get a very clear picture of who could actually occupy that role. And so when you actually go out and promote it you can describe the exact kind of person you’re looking for, the exact ideal skillset, the exact attitude because you laid it all out, very clearly, on paper.” – Erik Gross
    • Doing this up front is a service to anyone walking into the role. That person then walks into a role that is well-defined.
    • Erik shares a story from his time at IBM as a client / server developer. There was no explanation of what the role meant or what he would really be doing day to day. The onboarding document was outdated, and it took 3 weeks for him to gain access to the proper systems to make meaningful contributions.

37:53 – Thoughts on Employee Onboarding

• What are some of the questions Erik wishes he had asked in interviews based on the idea of writing a really good job description for someone?
  • What does onboarding look like? Erik loves to ask this question.
    • If the company doesn’t place emphasis on onboarding, it’s not a good sign.
    • In technology roles specifically, Erik values a set of onboarding documents with some knowledge of how to access credentials to required systems. Someone should be able to follow these without needing to bother existing team members.
    • “I never want to be that guy or girl that arrives on the team and is constantly asking people for information that they know should already be written down somewhere. Them answering is keeping them from their much more valuable work.” – Erik Gross
  • Is there an architecture overview of the systems in use?
  • Does an onboarding document include the tools one would need to install, where to get credentials, location of code libraries, etc.?
  • Employee onboarding is more than just HR stuff like payroll and tax information.
• If we look at this from the other side, how quickly can the entrepreneur impart context to new employees?
  • Relevant context would be things like:
    • Why the company was formed (i.e. purpose)
    • Who the company serves
    • The benefit people get when they interact with the company
    • The products and services offered to provide the benefit
    • How the products and services are delivered
    • Who new employees would work with to make a contribution to the above
  • A web developer needs more context than just being told to build an application to deliver actual value.
  • Erik says impart the context to the new employee, and then show them how to do the processes of their job.
  • All that context comes from doing the prep work of clearly defining the role (which Erik would classify as making the role occupiable).
    • Erik mentions doing all of the work up front somehow enables you to find the right person. It’s happened to him a number of times.
    • “I hire a lot of overseas developers and technical talent of all sorts…. I’ve found that every time I do a really good job of fully describing…the exact bounds of their role and what my plans are for onboarding them and how I’m going to pay them and how I’m going to do continuing education for them…which parts of my service or product will I have them do initially and then what will I have them do as they get up to speed. When I’ve defined all of that, now I can craft a really well-optimized job posting. And I get the kind of people that I want to be talking to to respond. And I can quickly in 2, 3, 4, 5 days filter through that…have 3 people I interview, and hire one of them.” – Erik Gross
    • When Erik does not do things like the above, he doesn’t get the right people as quickly, and he might not know the right questions to ask in interviews. Not doing the pre-work can make someone look unprofessional.
• Sometimes we put effort into building expertise in areas because it can bring us pleasure, and other times we build expertise to avoid pain. The pre-work we are talking about for the job descriptions and making the role occupiable is more of the latter.
  • Bringing on people means you are asking them to join you in a mission.
  • Certainly you need a viable, sustainable company that can pay you and your employees. But it was built for a reason.
  • “You can treat them just like they’re interchangeable, just like gears in a machine, or you can go ‘no, they’re not.’ When you treat them as individuals and care about the kind of people you bring in, it’s unbelievable how much extra they bring to the table that you never found out even during those initial interviews.” – Erik Gross, on treating people well by being prepared
  • Erik has consistently found the people he’s hired know about other things that surprised him in a good way. And it led to deeper collaboration. But it was due to getting clarity up front to make the role accessible and occupiable.

43:57 – Transferring Duties to Others

• Does writing the job description allow you to accept or let go of the fact that duties will be offloaded to someone else?
  • Erik says it does but not always.
  • At The Tech Academy, the hardest duty to let go of and offload for Erik and Jack was content creation.
  • Erik is very good at making curriculum and teaching. So is Jack. They had written nearly 50 job descriptions for the company before finally handling the curriculum / content creation role (including sales and delivery).
  • Part of their challenge was clarifying the thought processes, the background data, and the methodology behind imparting technical knowledge effectively.
  • “I can look at it right away and know, but it’s that expert’s curse. How do I articulate what went on in my evaluation of that piece of data?” – Erik Gross, on clarifying curriculum creation methodologies
  • Erik and Jack created an apprenticeship program in which participants would iteratively try to create a piece of content with feedback on each iteration. Upon each iteration, Erik and Jack would correct the person but also go back to the training materials they had created to determine what might be missing.
  • “You asked this question in the context of being unwilling to let go. There is nothing that you bring to the table as the business owner, entrepreneur, or creator of the thing…there is nothing you can’t transfer, even if it seems like it’s so intrinsic to who and what you are. But that was not an easy lesson for us to learn. We both had to learn that one.” – Erik Gross, on learning how to transfer their knowledge to someone else

Mentioned in the Outro

• The Power Offer sounds like something that could be used to propose new projects within your company and possibly to expand our scope influence within the company. Nick gives the example of a small problem with a marketing system indicating a deeper root cause that needs fixing.
  • Our warm network is our co-workers.
  • Another way to test our ideas is to share them with members of our technical community (in-person or online).
• Erik shared a good process the entrepreneur, business owner, or hiring manager could follow before creating a job requisition.
  • Identify the work someone in this role would need to do at a high level. It could be like Erik described, work that is getting in the way of more valuable work or a specific set of work that needs a dedicated person. Then get more specific:
    • What are the processes someone in this role would need to follow?
    • What are the tools the person in this role would use?
    • What systems would someone need to access in this role?
    • What knowledge do they require upon hire vs. what you will teach them?
    • Who will the person in this role collaborate with?
    • How will the work done in this role change over time?
    • What salary is appropriate for someone in the role?
  • Being very specific forces good documentation of processes and tools and the work being done, and it forces you to keep updating that documentation.
    • This also eases the transfer of responsibilities to someone else.
  • We discussed the necessity of giving a new employee context about the company, the purpose, and where the employee’s role fits. You can give them purposeful work and an understanding of that purpose as soon as they start!
• For more episodes on entrepreneurship, check out:
  • Episode 235 – The Best Bad Option with Al Elliott (1/2)
  • Episode 236 – Having the Vision, Charting the Path, Removing the Blockers with Al Elliott (2/2)
  • Episode 96 – Building Your Own Business From Idea to Operations with Ashley Connell

Contact the Hosts

• The hosts of Nerd Journey are John White and Nick Korte.
  • E-mail: nerdjourneypodcast@gmail.com
  • DM us on Twitter/X @NerdJourney
  • Connect with John on LinkedIn or DM him on Twitter/X @vJourneyman
  • Connect with Nick on LinkedIn or DM him on Twitter/X @NetworkNerd_