This week, I get the pleasure of asking Robb Dunewood 20 Questions. I found out about Robb few years ago while listening to Daily Tech News Show with Tom Merritt. Roibb is a cohost of the show and I have really enjoyed his point-of-view about technology. That beng said, I honestly do not know much about him, but her seems super interesting. One of the things I do know of him is that he lives in the Central Ohio area, and therefore I might be able to actually compensate him for his time and efforts for these 20 Questions with a beverage or dessert of some format.
Since I know very little about Robb, this will be fun. Let’s get to the questions…
In a previous career, I was a cartographer/GIS Coordinator. I came to that career due to my love of concepts of space and place. So, one of the things that I think set the table really well for a conversation in 20 Questions is finding out someone’s Geographic Story.
For example, my geographic story is that I was born as an Air Force brat just outside of Oklahoma City, Oklahoma. My parents moved to Montgomery, Alabama when I was 3. By when I was 3 , I mean, on my third birthday we moved to Alabama. I remember having my third birthday party at a rest area during the move… We lived in Montgomery for another year until my dad was released from active duty and found a job in the Magic City, Birmingham, Alabama. I grew up in Birmingham and moved away to college in Northeast Ohio at Kent State University. I followed my then fiance to the Columbus, Ohio area. I have lived in Columbus through getting married, having 2 kiddos, getting divorced, getting remarried and having 4 step-kids. Question 1: What is your Geographic Story?
I was born and raised in Northeast Ohio, about 70 miles from Cleveland and also about 70 miles from Pittsburgh. Growing up, families were divided based on if they rooted for the Browns or the Steelers. I lived my entire childhood in Ohio with the exception of 5th grade, where I briefly lived in Columbia Maryland. After graduating high school, I started college in New England, but, a sports injury brought me back to Ohio where I also attended and graduated from Kent State University. Grad school at The Ohio State University brought me to Columbus where I met my wife and have resided ever since.
Who doesn’t love Kent State. It is pretty amazing that the ending of our geographic stories is so similar… Aside from the 20 Questions I did with my ex years ago, this is the first Kent to Columbus culmination so far. I can tell you that I truly do love the Central Ohio area. I understand that it is not the most exciting place to live, but it definitely is a nice place.
Okay, since we are in the same geographic area, Question 2: what is your “go to” hole in the wall, local restaurant that you get excited to go to everytime you decide to get it? (yes, this is me trying to find another restaurant to eat at)
I am a huge fan of House of Japan over on Sancus Blvd., right in front of JPMC. It isn’t as fancy as some of the other Hibachi grills around town, but the food is delicious, the service is good, and the wait time, even during dinner rush, is not too bad.
House of Japan is fantastic. I have not been there in a while, but others in the fam have. I think my daughter went to a birthday party there not too long ago.
Here we are at question 3…I love this question because it either induces incredible passion or tremendous apathy. Question 3: Cake or pie? Which specific one and why?
I am not a big fan of either, but if I had to choose, I’d say pie. There are times when I am in the mood for a piece of Apple Pie or Sweet Potato Pie. I don’t know that there is ever a time when I’ve said, “You know what I could go for? A piece of cake. I don’t even like cupcakes.
So you are more of the tremendous apathy group. I get that. I am more of a pie guy myself, but truth be told, I’ll kick a baby for some cheesecake. Question 4: Is there any food out there that you cannot control yourself around?
I am a huge fan of Mexican food. I wouldn’t say that I can’t control myself around it, but, I could probably eat it daily for a week or 10 days before I would feel like I had enough.
Interesting choice since Columbus is now known for violence erupting at taco festivals. Sadly, my favorite taqueria, Taqueria Los Tizoncitos La Joya, that was located in the Crosswoods area closed. First Woody’s Wing House was demolished for one of 17 Sheetz opening in the area, and then La Joya closed. Cosswoods is a sad reminder of past meals. (this past paragraph is for all y’all Central Ohioans)
I know this next question is a hard left turn, but I do not want this to become a food only interview… so here we go. I have always loved your balanced and realistic opinions concerning tech and the world. So, since it is a big thing right now… Question 5: Do you think that a generalized AI will ever be truly “intelligent” and not merely a better statistical probability output that closely approximates a human?
So, I don’t think that AGI will be intelligent in the way humans are. These systems already have access to literally all data that has been written and digitized, and if they only just get better at predicting the next letter, essentially what LLMs do, they will improve to the point where they have the appearance of consciousness. Some will argue that machines will only appear to be sentient and not actually conscious. I’d argue, what's the difference if humans can’t tell?
I have had that “what’s the difference if humans can’t tell?” question roaming around in my head as well. Specifically, how is it really different than how humans think anyway… This is the part of AI development that is really interesting to me. We are learning more about how humans actually think by trying to get machines to better approximate that.
Question 6: How did you end up in the tech pundit space? What drew you to technology and then what drew you to making a living talking about technology?
I have been into technology ever since I was a kid. I got my first computer, a TI-99/4A, when I was 11 and started writing code shortly after.
I didn’t actually go to school for computers. Computer Science was different pre-World Wide Web. It wasn’t even invented until my senior year in high school. But, once, I got into college, things really took off. I was too far along into pre-med to change my degree, but, I did get a minor in Computer Information Science and started working towards a master degree in the space, but, the corporate world came calling.
I worked my way from a consultant to the executive levels of management at various software companies, and along the way, started blogging, teaching, and podcasting. I don’t have that I hated my job and had to strike it out on my own type of story, but, in 2017 i started preparing to to become a full-time creator. I left the corporate world in 2019, and and haven’t really looked back since.
Having been caught in a RIF and not getting any traction for new employment, I envy your move to self-sufficiency. With this economy today, I don't know when or if I will get gainful full-time employment any time soon. I need to focus on just working my part-time job and trying to score some commissions and contracts.
Question 7: What part of the technological world has you most excited right now, what part has you most concerned?
I am most excited about the equalizing force of technology, particularly in media, and how its use has essentially removed gatekeepers that used to control the dissemination and distribution of information. A creator with an email list or social media following can rival corporate media with billion dollar budgets when it comes to getting a message to the masses.
I’m most concerned about the speed at which AI could displace jobs across wide sections of our workforce, and, because the technology can be applied to so many industries at the same time, we won’t be able to recover in similar ways to other technological transition periods in history.
Technology can definitely be a great equalizer and democratizer. The biggest issue I see with this equal flooring is that an uneducated boob with a good following can have more influence than a well-educated specialist with a smaller audience. But that is the rub of today’s connected society. In the early 00’s I loved watching the democratization of the music landscape. The rise of the middle class niche-market celebrity, so there are definitely examples of this democratization of connection working.
Weirdly, I do think AI (if applied properly… that’s a biiiig “if”) could help with this influence disparity… but you are very correct that the speed of AI roles and their evolution in the workplace is alarming. You can definitely see its influence in the UX industry where I am trying to get new work.
On a different tech angle… My ex-wife is bir-racial (white mother, African American father) so my 2 biological kiddos are biracial as well. I love that you do the TheTechJawn.com. I love that there is a tech resource out there with a POC viewpoint. Question 8: What do you see as a difference between how tech is reported on by “Wypipo” and how it is reported on/commented on by POC?
One of the biggest differences I see is perspectives. One of the things I regularly say about Tech is “Tech is Tech, but it often hits different in different communities.”
There is a lot of bias in tech, not because creators of said tech intentionally mean to be discriminatory (some absolutely do, but that is not the point I’m making here), but because the mostly white, asian, and male product team didn’t think to run more testing on diverse data sets. Entire groups get overlooked, not because of malice or ill intent, but because the creators of tech didn’t think about them… The result for the marginalized often feels the same regardless of the intent.
The same bias exists in media coverage of tech. Because tech affects my community differently, I wanted to cover it from the perspectives of those differently affected or disaffected.
There is definitely a privilege to being in the population with privilege. It sounds very tautological being put that way, but truth is truth. The insidious thing about privilege is that it is often completely transparent to the ones with privilege. It is the air we breathe. Do fish notice the water they are swimming in? Privilege is quiet and treacherous. It is oppressive to both the privileged and the underprivileged. I did not see any of this until I was in an interracial relationship, I was treated differently than my white counterparts who were not challenging the status quo in Alabama and Ohio in the late 1990’s. Very eye opening.
Question 9: Do you have a favorite piece of technology (aside from computers and phones)?
Being a full-time creator, I’d say my favorite tech beyond computers and phones would be cameras and microphones. These are amongst the tools I use, darn near daily, to create the content I use to sustain my livelihood. I don’t necessarily use them as much as some of my wearables or even IoT devices, but, beyond my phone and computer (tablet), they are the tech I’d miss the most if I didn’t have them.
I imagine that as a podcaster good cameras and better mics are an absolute necessity. Similar to good brushes and canvas to a painter.
So question 10 is a question I always ask at 10. It’s less a question, honestly, but more a fill-in-the-bkank. Question 10: I find that I am mostly ______, but I find that others feel I am mostly ______.
I find that I am mostly introverted, but I find that others feel I am mostly extroverted.
That is really interesting. Question 11: Why do think that there is such a discrepancy between your understanding of you and what you feel others understanding of you is?
I think people see me in front of a camera, on stage, leading teams, being very personable, and assume based on their interactions with me that I am a people person. I'm not shy or uncomfortable around people, but,I am not energized by being around people like extroverts are and there is limit on me being social. I'm never the last one to leave the party. Even when it is my own.
I think many people do not quite understand that extrovert and introvert doesn’t mean that an introvert isn’t able to be interactive (even with large groups of people) or that an extrovert isn’t uncomfortable with public speaking. Typically introvert and extrovert has to do with social battery and how they recharge. I bet you are fantastic 1 on 1 at a party, and even better at brunch the following day.
Simple question that is relatively profound.. Question 12: Overall, are you happy?
Simple and easy to answer.
Absolutely and profoundly yes. Life always has its ups and downs, and I've had situations that I was unhappy with, but even through those situations, my overall happiness has remained extremely high.
That is an absolutely fantastic answer. I have always loved it when people I ask 20 Questions answer this question with an enthusiastic affirmative. You would also, probably not be surprised how many people haven’t thought about this recently or even at all.
Here we are at Question 13. Triskaidecaphiobiasts rejoice, we are at 13. Question 13: Do you have any superstitions or rituals in your life? (for example, crossing paths with a black cat would be more superstitious, while needing to meditate for 20 minutes a night to be able to sleep would be more of a ritual).
When I shoot free throws, I spin the ball in both hands, take three dribbles, spin the ball again, pause, then shoot. I have shot the same way since middle school.
It just doesn't feel right when I don't go through this routine.
There are so many routines and rituals associated with sports. I know that I had a very particular sequence of movements to get dressed for my soccer games. I wasn’t the elite player that I wanted to be, but I was committed to playing. The rituals associated with the sport were about transitioning from not being an overly competitive individual to being competitive on the field.
Question 14: If you could have dinner with 5 people currently living or previously living… what’s on the menu? What are you feeding these 5 people from all of time and space?
I am not a foodie at all, so I would definitely be taking these 5 people to restaurants of their choosing, but, here is my list folks, in no particular order, that I would love to sit down with and pick their brains over a tasty meal.
Martin Luther King Jr. - I'd love to hear his take on the progress made towards his dream since his passing.
Justin Welsh - I can't say he coined the term Solopreneur, but, he is who I think of when I hear it.
Myron Golden - Entrepreneur, Author, and Business Coach that stresses biblical principals in business.
Joy Ann Reid - Is actively building an independent media platform which is rivaling the corporate titans she was recently dismissed from.
Lamar Tyler - Founder of Traffic Sales and Profit, Author Speaker, and Business Coach
Good list!
I like that mix of people. You definitely have an entrepreneurial direction in your selections.
If I had to suggest a food, I think that I’d suggest wings. They are highly variable, you can make them, as fancy or as simple as you need. Almost every culture, and definitely every culture that has developed around the existence of chickens, has some kind of wing to enjoy.
So, Question 15: What kind of impact do you hope your work has on the people who follow you, listen to you, or learn from you?
As an entrepreneurial content creator who’s been pretty successful in both the corporate world and as an entrepreneur / small business owner, my hope is that my content inspires those interested in creator businesses and provides a travel guide of sorts that speeds the process up for those along the same type of journey.
Well, I for one can tell you that I have enjoyed all your appearances on podcasts that I listen to where you have guested. Your take on tech is super welcome because it has a firm base in the actual corporate world. You speak from experience and knowledge.
We are on the home stretch now. Question 16: Is there a question that I haven’t asked that you either expected me to ask, or would have liked for me to have asked?
I can’t say there is a question I expected you to ask. Happy to answer, whatever you throw my way.
Then let me be kind of sincere for another question. Question 17: You’ve worked in both corporate and creator spaces—if you had to pick one piece of advice to give someone who wants to make that leap, what would it be?
Start preparing for the leap well before you intend to take it. I strongly recommend doing the thing on the side until what you do on the side can be done for a living. The biggest mistake I see people making when leaving the corporate world for a creator business is not having saved enough to sustain their lifestyle enjoyed by that corporate paycheck.
Definitely sound advice. I wish the decision to leave corporate America was mine to make a few years ago. It would have been much better for my retirement accounts and stress levels. That being said, I do enjoy freelancing when I can find a contract.
Okay… Turn about is fair play. After being peppered with 17 Question… Question 18: What question or questions do you have for me now?
Why me?
What made you want to ask me 20 questions?
That is an interesting question. I think there are a couple of different dimensions to my answer.
Firstly, you seem interesting and intelligent and some of your interests align with mine. I have been drawn to your tech analysis because it is very grounded and tends to cause me to think of things differently when our opinions do not match.
Secondly, you seem kind, and I would venture to say that this interaction with you has solidified that understanding of you. I have never seen you be mean or nasty to anyone,nor have I even heard inklings of that kind of behaviour about you. That being said, I have also not seen you in the paint on the court. You might not be so kind when there is a game involved.
Thirdly, I am trying to broaden my perspectives. I have biracial children and a pittance of perspectives from people of color. Most of their life and upbringing has been in surroundings where one might describe it as predominantly white (with a hard pronunciation of the “w” and “h” in that word). This is something I am making an effort to remedy while trying to not put the onus of my exposure onto the POC I am reaching out to. It is not a person of color’s responsibility to get me more aware of other cultures. It is mine, so when I find a voice in the wild from a different cultural background than me that is a compelling, intelligent, and kind voice, I do what I can to learn more. I am trying, and it is trying to be trying.
Question 19: What, if anything, are you taking away from these 20 Questions that you did not bring in with you?
I am continuing to realize that people actually hear, and in many cases, care about the things I have to say.
That may sound a bit strange coming from a podcaster who has been behind the microphone as long as I have, but, in my mind's eye, when I am speaking to my audience, I visualize it as though I am speaking to a single person. People generally listen to podcasts alone unless they have a captive audience in a car, so I create content hoping the listener feels like I am talking directly to them.
Sometimes, I forget that I am having one-on-one conversations with thousands of people simultaneously, and though I may not know my listeners personally, they know me. I feel as though I need to lean more into the community that has formed around the content I create, and is one of the reasons I am being more intentional about doing things like answering 20 Questions.
People definitely hear and care. I love that I have gotten to know you significantly better, and, in turn, that you have gotten to learn more about at least 1 person who consumes at least some of the content you generate. That being said, para-social relationships are an interesting thing. They really didn’t exist until the ubiquity of the broadband internet. I guess they could have existed with Betty Crocker recipe submissions and Dear Abby, but there is a weird intimacy of knowing so much about one person who knows little to nothing about you.
I would love to think that if we encountered each other IRL (an occurrence that might actually happen due to our geographic proximity), that I could consider you to be a little more than an internet acquaintance. I think I would consider our category as Internet Friendly. We aren’t quite Internet Friends, but have interacted more than just being acquaintances.
Here we are, my good man, we have made it to question 20… sooo… Question 20: What’s next? Be as concrete or abstract, as short-term or long-term, as direct or metaphorical, as personal or generic as you would like.
That's a timely question! This is the time of year when I typically start planning for the upcoming year. For over two decades, my content creation career, including writing, podcasting, and general content generation, has predominantly focused on technology. While I've discussed, coached, and even consulted on entrepreneurship, my public content and persona have largely been defined by technology and my role as a tech podcaster.
Relatively recently, I've begun to create more public-facing content about being a full-time creator, detailing how I'm building my business, what's succeeding, and what's not. Although I will definitely continue as a technology-focused podcast host, I plan to broaden my scope to include more content on content marketing and solopreneurship within the creator economy.
So, what's next?
You can anticipate more podcasts, newsletters, public speaking engagements, and coaching on running a content-centric solopreneur/small business with a focus on podcasting.
I’ve been telling folks lately that I’ve been podcasting for nearly 20 years and during that time have made a lot of mistakes, done a few things right, taken good notes, and maybe even made a dollar or two.
My plan is to increase these types of conversations while maintaining the technology podcasting, which is so near and dear to my heart.
Robb, you are an amazing person, and I am truly happy to have gotten top know you better. I owe you a beverage/dessert/meal/drawing… something. Wouldlove to meet up with you IRL. Please give Robb a follow on Threads, Insta, and Substack all @RobbDunwood). He is one of the best. Check out his website, RobbDunewood.com, for more information, and listen to the podcasts that he is a part of… DailyTechNewsShow.com and TheTechJawn.com
Robb is a delight.
To recap:
Been a bit between posts
Got a freelance UX contract I am working on
Still working at the local petfood store
Need significantly more sleep than I am getting
But I always need more sleep
Water main broke in the neighborhood today
Water is just now starting to work
Superman was amazing
On question 10 with a different interview
Hope to get to question 11 soon
It has stalled to say the least
Suggestions for topic next week?
Any are welcome
Anyone want to be interviewed?
Lemme know
Okay, Imma call this one done
Have a great week everyone