It’s officially been one month since I started conducting interviews, and two months since I decided to pivot my strategy. The last month has felt like the longest of my life but has also passed in the blink of an eye.
Perhaps the most notable transformation has been in my mindset. Strangely, I feel as though my personality has changed. Or perhaps it has regressed to a prior state.
I finished college with a Bachelors in Entrepreneurial Studies which is a pretty silly degree. I learned a lot of useful things1, but there is no substitute for doing by learning.2 I chose this major because it was easy to finish, but this was also the major that best fit my personality.3 I moved to San Francisco right after college because I was enamored with all things startups and tech.
I quickly learned that in order to be effective in that word, it helps to have a skillset4. Thus, the journey began to gain some skills and ended nine years later working at a 16K person company.
In my free time now, I listen to startup podcasts. I’m reading books like the “The 4-Hour Workweek” and getting stucked in to hustle-culture YouTube. I’m also watching far too many luxury real estate videos5.
I have become rather ambitious and perhaps delusional with my goals; I feel like a walking stereotype of “startup guy.” As silly as I feel sometimes, I have full conviction that I will succeed.
The Big Unfair Advantage
I always assumed I would found a tech company. But for most of my career, I’ve been a frontend platform engineer that works with marketing data. Unless I start a business in that space6, I’d be better off finding a job at a startup and learning how to be a proper fullstack product engineer.
Right now, I want to work for myself. I want to tie my efforts directly to my outcomes.
The other area of expertise I have is interviewing software engineers. I’m probably one of the best people in the world at this. A lot of engineers could be great this. But most engineers don’t spend their Saturdays writing interview questions for fun8. I became good at this because it’s something I love working on.
It’s also the perfect time to launch a business in this space. LLMs can now solve most coding interview problems with ease which makes it easier to cheat. The way software is being written with LLM coding tools is changing how the job is done. The standards for interviewing software engineers are actively being reset.
The Big Pivot
As loyal readers know, my first attempt to make money doing this was to offer consulting services to help companies improve their software engineering hiring. The feedback I received from companies was pretty consistent: “This sounds interesting, but it’s not a priority right now. We just need to hire people7.” So I decided I would become an agency recruiter.
I must confess, many aspects of the job don’t appeal to me. It’s essentially a combination of being a salesperson and a matchmaker. But it has proven to be the right move:
It gets me closer to companies. By offering to solve an immediate problem (we need engineers now), I can establish a relationship and prove my expertise. They’ll know firsthand I’m an expert at evaluating software engineers.
I am gaining greater visibility into the hiring problems companies are facing and I’m even more convinced my skills are badly needed.
An agency recruiting business run by a software engineer who pre-screens candidate will be very lucrative. There is a ton of challenging and tedious “people work,” but the rewards are direct and tangible. After being funemployed for most of 2025, I sure would like some money.
As challenging as the “people work” is, I’m good at it. I worked in sales for a year, I know how to put my nose to the grind and get the work done. I also know how to ride the emotional rollercoaster that comes with it. Eventually, I’ll be able to replace myself with people better at this than I.
The Big Hypothesis
In chapter 1, I made the assertion that there are good software engineers hiding in plain sight. Since then, I have proven that to be true; I have a ~33% pass rate. Here are the reasons why:
I’m very good at evaluating engineers. I actually forgot how good I am since I hadn’t interviewed since 2024. And I forgot how bad most companies are at this.
Companies are foolish for not giving more candidates a shot. They are still generally attracted to signals like “good college, good past companies”. I understand why they do this, but they are missing out on a ton of great talent as a result.
In that same vein, their interview questions are poorly written. I’ve seen this first hand doing some initial consultations. Poor questions filter out good people and fail to test for relevant skills.
Many great engineers aren’t the best at marketing themselves or they don’t shoot for more competitive jobs. I don’t strictly screen everyone that comes into my funnel. I give pretty much everyone a shot as long as they fit some basic criteria9.
These diamond-in-the-rough software engineers find me. On a typical day, I might have three coding interviews scheduled, but many candidates reschedule or cancel at the last minute. I’ve found that the engineers who actually follow through with the interview turn out to be pretty good. My guess is that these engineers have conviction in their skills. Their tendency to show up to the interview is an indication of that.
The Big Challenge
So far, things are going quite well. Honestly, it’s going a little too well. But I believe this is the case because there is a critical gap in the hiring market and I’m uniquely skilled to fill it.
One lovely surprise is how many of my former colleagues have reached out with encouragement. They administer the questions I wrote on a weekly basis and have full confidence in my skills. This has helped me stay the course when I have doubts about this path. I’m going to print out those messages and post them on my wall.
The next big challenge however is convincing people who haven’t worked with me that I can find them great engineers.
The Big Sleep Deficit
Over the past month, I’ve done several jobs:
Building the interviewing platform and talent portal (kind of an applicant tracking system, but specific to my use case).
Writing interview questions.
Conducting coding interviews all day, every day. This is absolutely exhausting and no one should ever subject themselves to this.
Sourcing candidates.
Convincing companies to hire through me.
This coming week, these are my tasks:
Conduct just a few interviews.
Specifically source for candidates that match what my customers are looking for.
Find more companies to hire the great candidates I’ve found.
Write new interview questions; one for a customer’s specific hiring needs.
But perhaps the biggest and most important task is to take a break. I have been burning the candle at both ends and there is a notable degradation of my health, both physical and mental10. This is, of course, impacting the quality of my work and is ultimately counterproductive.
In my hustle-culture YouTube binge, I came across this quote: ”slow is steady, steady is fast.” It’s time to embody this. I will relax once I place my first candidate and make some money. But that first win always takes longer than you think. Until then, I need to work steadily.
I also need to reset my foundational habits. Disconnect from work around 8pm so I can fall asleep on time. Go on daily runs. Spend 30 minutes every day doing chores. Do a proper grocery trip. Food prep so I always have healthy options for breakfast and late night snacks. Reach out to more friends, maybe start a weekly dinner ritual; I’m a very social creature, I’m going crazy without an office to go to or coworkers to interact with.
A former roommate reminded me that I have a pattern of always sacrificing my health to grind. It’s time to break that pattern, I mean it this time!
The Big Vision
Aside from fantasizing about buying this penthouse, I’m thinking a lot further ahead about the business. Hustle-culture YouTube told me to do this.
I am already thinking about bringing people on to do all of the jobs I outlined above. 1-2 dedicated people for sourcing, finding new business, and matching candidates to companies. I also hope to find several part-time engineers to take on the bulk of interviewing. Doing it well is an exhausting job and I suspect it’s best to address this with horizontal scaling. This might be appealing to those working on their own startups or who are semi-retired.
Ideally, that will leave me with time to work on writing interview questions11, sales, relationship building with clients, and becoming a LinkedInfluencer12. All of these are founder-type jobs anyway.
I originally got into this business because I wanted to help companies improve their hiring. The 2027 goal is for Eng Hiring LLC is to achieve this vision and change how software engineer hiring is done for the better.
The Big Walking the fine line between confidence and Dunning-Kruger
I have complete conviction that I will succeed and accomplish all these goals and more. This is all predicated on the belief that I am one of the best people in the world at evaluating engineers. There are already GOATs🐐 like Gayle Laakmann McDowell and Aline Lerner, but my goal is to disrupt the coding interview, not just join the hall of fame.
That last paragraph was a bit embarrassing to write out, but also one that I fully believe in. This confidence is concerning at times; I worry it will make me blind to criticism and stunt my growth.
And yet, when I’m conducting an interview with one of my questions, I can see the gears turning in the minds of my candidates. I know how to precisely throw wrenches in their solutions. I know a dozen ways to guide them and which one to choose. I see the moments of inspiration when they formulate solutions.
And during the rare interview, I encounter the sublime: software engineering greatness.
1 The best professors and classes were by former industry professionals who had worked on startups themselves as opposed to professors who were primarily interested in research.
2 Which very much applies to my coding classes too. I didn’t fall in love with programming doing my homework. I fell in love when I was working on an optional prototype for a different class project.
3 I was often thinking of business ideas in college. The only real idea I followed through with was bike reselling. I bought cheap used bikes in winter, waited until the Spring when there was high demand and sold them. I made good money but it was very labor intensive and not worth the ROI. A very valuable lesson to take from my first failed business.
4 My only skillset was working with bikes, which I actually did for four months to make some money while I job searched.
5 This is rather embarrassing to admit, but I want to be honest with you. My aspirations are now much higher than a one bedroom co-op in Manhattan.
6 The best I can think of is finding a better way to do client side tracking. There is actually some opportunity here since cookie regulation and whatever Google Chrome is doing has thrown the industry into disarray. But this is a very challenging problem space with a lot of external powerful forces (see aforementioned government regulation and Google Chrome). It’s not one that particularly excites me either and I don’t really like the customers of that business (I’ve been dealing with their difficulties my whole career).
7 The irony being that if they invested in their process, hiring people would become faster and more effective. But I get it, it’s hard to shop for vegetables when you’re overwhelmingly hungry now.
8 My work on engineer interviewing never got me a raise. It was helpful for promotions, but I never got the impression it moved the needle in any way when it came to compensation.
9 They have to live in areas that are relevant for my customers. Right now I’m focused on hiring in NYC since I’m working with startups that require being in office.
10 I invited a friend over today so I was forced to clean my kitchen. I’ll spare you the gross details but it had basically become a biohazard zone; I cleaned it with a mask on. Sorry if that’s TMI, but I want to be honest about how hard starting a business is and the unfortunate side effects.
11 This is one task where I’m a bit doubtful someone can replace me. Though I did do a lot of interview question review at Square. Perhaps I’ll target this as part of my 2028 vision.
12 I’m sorry to all my connections for my relentless posts. I find it just as annoying as you. Know that I post only to promote my services. I try to make them as entertaining as possible though.
