I Hired College Students to Run My Business (PK&C WINternship 2020 Report)

December 2020 marked the first winter after I graduated from college. I built the winter break internship that I wish I'd been able to experience myself and offer it to current Grinnell College students. I hired Grinnell students because they fit in well with my random approach to business hours, project-based work philosophy, and communication patterns because I learned all of those things in college. I built my business as a college student, so I have a competitive advantage when hiring from an untapped market and trust the people I hire way more than most businesses would be able to. This is a complete report on the process and results of hiring, onboarding, working, and shipping with my interns.

WINterns Group Chat

When I attended Grinnell College, I never knew the best way to spend my winter breaks. Five weeks always seemed like too long to do nothing but not long enough to get anything done. My freshman year I worked at my hometown Trader Joe's. My third year, I battled debilitating anxiety symptoms at the tail end of internship-finding season. My fourth year, I wrote the beginnings of Writing for Software Developers.

But, my sophomore year, I had a proper internship. It was an extension of a job I held part-time during the academic year, a remote data science role at a Wisconsin insurance company. Over winter break, I worked there full time, joined the team for standups and meetings, and even went to headquarters in Madison for a week, my first and only business travel. It was an enlightening experience and my first time working in person in a professional setting. I wore a suit and gave a presentation to proper executives. In the years that followed, I looked for dedicated winter break internships, but didn't find many. I imagine most companies don't think it's worth onboarding college students for a few weeks.


I filled all available positions in less than 24 hours ... on a weekend.

Friday night, I sent the following email to the Grinnell College CS Students mailing list, which is often used for distributing job applications. This is the only thing I did to advertise the internship. Here's the email:

Dear Grinnell Students,

TL;DR: I'm looking to pay $1,515.36 each to up to three smart and motivated Grinnell students to solve business problems using a combination of cleverness and code over winter break, working on your own schedule for a month. Guaranteed you'll learn a bunch that you won't encounter in the classroom or any traditional job.

Hi! Many of you may know me because I graduated in the class of 2020. For those of you who don't, my name is https://philipkiely.com and I am a Grinnell CS alum. I run a small business, taking the initiative to research exactly what I do is part of the application criteria. I like reinvesting some of my revenue in people, in 2020 so far, my company has paid out more than four thousand dollars in wages, entirely to fellow Grinnell students.

I’ll give you a hint: the most lucrative thing my business does currently (outside of my contracting activity) is selling copies of a book with a net profit of $34.44 per sale.

I am offering a unique winter internship opportunity to up to three highly motivated current Grinnell students. The program is of course fully remote and runs for the entire duration of winter break. It is a set-your-own schedule sort of thing, but there is a general expectation that a lot of work and learning gets done. Philip Kiely & Company is a pretty awesome place to work for 5 weeks. Tell your smartest friends to apply too so you can work together.

The program includes a stipend of $1,515.36 and is unfortunately only available to US citizens/permanent residents living in the United States. I would love to be able to hire international students but unfortunately work authorizations being what they are and my company being as small as it is I cannot at this time. If there is mutual interest, there may be room for one or more interns to continue after winter break on a part time/hourly basis. This is legitimate 1099 employment, with W9s and taxes and whatnot.

So, what is the actual program? Basically, it is an open-ended opportunity where you take one of the problems with my business and try to fix it in five weeks. Take all of the skills you’ve been practicing in school and apply them in real life in a relatively low-stakes environment. You’ll have a bunch of support and resources as you work, and you’ll get to learn directly from me and observe some of my daily work. It is not expected that you write code as part of the internship, the solution to each of these problems is probably mostly words, although some of them could benefit from some sort of code as well.

Part of the interview will be talking through what my business does and what things you could potentially work on are. Here is an incomplete list of problems that you could choose to work on, or you could find a combination of them, or you could figure out a different problem with my business, and the problems are of very different size, so some are not worth a whole internship on their own, some may need to be scoped smaller to fit in 5 weeks:

  • I don’t have any meaningful email list and I really need one
  • My content production schedule, distribution plan, and syndication efforts are sporadic, scattershot, and nonexistent respectively.
  • I want to appear on at least 8 podcasts as a guest in the next couple of months, but I have nothing booked
  • I have the setup for a physical brand and design but I haven’t managed to launch anything yet. Also, I need quite a bit of design/rebranding
  • I need to organize and systematically contact several dozen famous people as part of creating Writing for Software Developers 2
  • I need to create high-quality video content for Cold Email for Interesting People 2
  • I need to perform multiple rounds of high volume but extremely personalized sales outreach
  • I'm trying to spin up an editing agency

A good rule of thumbs for success on a solution or the validity of a problem to work on: will it sell 44 books? If so, it pays your stipend, we’ll go for it.

Here is how applying works:

  • Send me an email to philip@kiely.xyz (NOT a reply to this email or this Grinnell email address)
  • Tell me about your aptitude for business, your technical ability, and your knowledge of the creator economy. It is okay if the answer to some of those is “none yet”
  • Describe an independent project that you have completed within the last 2 years, links appreciated Talk about which problems you’d be interested in learning more about. Triple bonus points for pointing out a problem that I haven’t seen yet.
  • People from all class years are encouraged to apply I care about aptitude not age. That said, and I really hate to say this because I was 17 for most of my first year at Grinnell, you do have to be 18, again because my business is not big enough to be configured to work with you otherwise.

I’ll be accepting applications until Dec 15, but this is a rolling process, once I have 3 people I like the program is full. So, apply soon. If you apply, you should have an interview within a day or two and a decision right away, this isn’t one of those applications that takes forever to hear back from.

Of course, also email me if you have any questions. philip@kiely.xyz



A few key things from this message:

  • The stipend is approximately what I earned the winter break I worked at a grocery store, adjusted for inflation, rounded to the nearest net income from a book sale.
  • Different people have coined different terms for it, I like Joel Spolsky's “smart and gets things done.” I'm filtering for this in the job posting by having the sole hurdle to apply being figuring out what my business does and also by having the applications be rolling so that speed of response matters.
  • I leave what I'm looking for intentionally open-ended to increase my reach and my chances of finding someone I didn't even know I wanted.

Three people applied within the first 24 hours, and I interviewed and hired all three of them day-of. Three video calls back-to-back on a Saturday sealed the deal. Rolling means rolling. I didn't see myself turning down any of the applicants, so I figured there was no point in leaving the application open and having to make a tough decision or overreach my budget.

Here is who I hired, in order of hiring. I'll be presenting their work in this order throughout this writeup for consistency. I've included, with permission, the emails they sent to get the job. While everyone ended up working on slightly different projects than they originally proposed, I think everyone did a fantastic job of understanding my business and its needs. If, after reading this, you want to hire any of them, send me an email and I will make the referral with an enthusiastic letter of recommendation.

Jeev Prayaga, Design & Development

Hi Philip,

Hope you're doing well! My name is Jeev Prayaga and I’m a rising junior at Grinnell, currently on a year-long leave of absence. I came across your email in the CS email list and decided to seize the opportunity to apply.

After reading a little more about your work (as a programmer, writer, and consultant), I was inspired by your thoughtful approach to blending content and code to solve problems. I was particularly drawn to your book, Writing for Software Developers, which seems to be an accessible (and incredibly useful) guide for budding software content writers.

I believe my skills and experience would be put to great use at Philip Kiely & Co. Though I am a computer science major, I’m always trying to think outside the software “bubble” and explore ways code, design, and writing can combine to create successful products.

In terms of potential work, I think my skills would best be suited to your efforts to:

  1. Launch your physical brand and design. I’ve been obsessed with graphic design, UI/UX design, and web design for almost a decade. I have experience working with design tools like Sketch and Figma and would relish the opportunity to dive into a brand refresh.
  2. Spin up an editing agency. This is a really intriguing avenue that I’d love to learn more about. I know your success as a freelance tech writer is a core component of your business, so I’m interested in how you can harness that success and kickstart this new editing business.

The two business challenges above stood out to me first, but I would be more than willing to contribute wherever I’m needed. I know you said this is a relatively low-code internship, but I’d also love to take my software engineering skills to the next level. My programming languages include Python, Java, JavaScript, SQL, HTML, and CSS, and I also have internship/project experience with frameworks like Flask, Vue, and Electron.

A recent independent project that I am particularly proud of is a COVID-19 Activity Risk Calculator web application that won "Best Application" at the 2020 COVID Computational Challenge, hosted by RMDS and the City of Los Angeles in May. My team worked to help users evaluate the risk of leaving their homes based on a personal risk profile, a neighborhood-based risk profile, and an activity-based risk profile. I worked primarily on the design and development of the app’s frontend, which I wrote in Vue, HTML, and CSS. The working URL for the app currently only works if your IP address is in LA, but you can view the code on GitHub.

If you’re interested, you can view more of my projects on my personal website. I've also attached my resume for your consideration.

Thanks so much for offering up this opportunity and taking the time to read my application. I'd love to interview to chat more about this internship and I look forward to hearing back soon.


Jeev Prayaga

Hallie Nuzum, Sales & Outreach

Hi Philip,

I am a third-year student at Grinnell and am interested in interning with you this winter break.

Throughout high school, I ran a business with my dad where we sent people personalized, hand-written messages on eggplants, potatoes, and other produce (called MyVeggieMail, website was taken down once I left for college). My main responsibilities were fulfilling orders and marketing through social media. Over about 2 years, we reached over $15,000 in sales. In this experience, I learned about marketing and profit maximization.

I have taken the two introductory computer science courses as Grinnell, so I have a solid understanding of computer programming overall and am proficient in Scheme and C, and I know how to utilize programming to be more efficient and exact. I also have experience using Excel in multiple course contexts and in professional settings from working at Burling Library. Additionally, I am proficient in using statistical software such as SPSS and Minitab.

I do not yet have knowledge of the creator economy.

Last year I was the community service leader for the women's Swimming and Diving team, where I organized monthly community service opportunities with the men's leader for the entire team of 70+ people. For the month of October, we created a food-and-good drive that had not been done in past years. The idea was to split up the team into groups to go "trick-or-treating" in the nearby neighborhoods on Halloween for food and other goods to donate to MICA.

We had to devise a plan to decide which houses we would go to, to notify the families in the houses that we were coming so they could properly prepare, and to make it clear to the groups about which houses they were to go to. I designed the attached flyer that we handed out to the houses a few days before Halloween to give a straight-forward message about who we were and what our purpose was. We also created a map to break up the pre-determined houses for out groups to go to. In the end, the event was a huge success, and we collected over 400 pounds of food.

I would be interested in learning more about your production schedule, distribution plan, and syndication efforts because I have strong organizing skills and enjoy simplifying things with schedules. I am also interested in working with your sales outreach because I think it mirrors my experience with MyVeggieMail, and I would be interested in maximizing the effectiveness of the outreach while also be efficient. Additionally, I am interested in learning more about booking podcasts because I am an avid podcast listener and would love to learn more about the industry while utilizing my planning skills.

Thank you for your consideration, and I look forward to hearing from you.


Eva Hill, Editing & Content

Hi Philip,

I just noticed your email about the internship opportunity with your company, and I wanted to reach out to express my interest!

With regards to my business aptitude, most of my previous experience comes from the small-scale manufacturing. I started an Etsy shop earlier this year, where I sell face masks sewn from a design that I created and perfected myself this past summer (https://www.etsy.com/shop/OverdressedDesigns). I manage the shop's finances, advertising, and production, as well as shipping and logistics.

I also have significant journalism writing training, which maps well onto advertising-type writing and general consumer-engagement knowledge. My current academic interest is in the sociology of popular and news media, so I've done a degree of study into the creator economy and have spent significant time analyzing social media as a method of information distribution.

My primary technical aptitudes are as follows: * I am an excellent writer, even by the standards of Grinnell. I can write copy text right the first time, with no significant edits needed. * In a similar vein, I am an extremely good text editor. I previously worked in editorial production at a design firm where all but one staff member had no post-secondary writing training. At that job, I honed the ability to smooth out text for an easier, more engaging read without changing the tone or core ideas. * My logistical organizing skills are highly refined from my role as news editor at The Scarlet & Black, where I'm regularly juggling multiple different writers and artists' assignments several weeks ahead of when they're due. * In terms of coding knowledge, my experience is limited (primarily R Markdown and related), but I'm a fast learner and have good understanding of the basics of coding.

In terms of the opportunities provided by this internship, I'm most specifically interested in the problems posed by your outreach goals, particularly booking podcast appearances, reaching out to celebrities, and performing sales outreach.

Based on looking at your website and reading your job description email, I believe I could facilitate these goals by helping you to develop a strong, consistent outward brand personality - there's a lot of interesting content and humorous, engaging writing there, but since the content creator industry is so oversaturated, those things really need to be taken to the next level to stand out.

You mention wanting to work on branding in the job description, and I would like to see what effect it would have to do a close reading of the front page of your site, rework it for a stronger immediate impact on visitors, and then develop that into a multi-pronged campaign to get both customers and celebrities/podcasters on board.

I look forward to hearing from you!



Michael Andrzejewski, Client Project

Michael was already working for me on a client project, his work with me remained unchanged, but he joined in the weekly meetings and group chat with the other interns.


With only six weeks, I had to move fast on onboarding.

The legal logistics were simple: everyone is an independent contractor, send me a W9 and your Venmo handle (one day I'll need a real payroll processor, but not until I regularly need to send more than three thousand dollars per week), and sign this two-page agreement that basically covers what “work for hire” means. My contracts are in plain English and have no restrictions or gotchas.

With everyone hired, W9s filled out, Venmos set up to receive stipends, and contracts signed, it was time to get started! My onboarding challenge was simple: I needed to get the interns familiar with my company and the creator economy as a whole and then provide them with project descriptions in that context. I wrote a few onboarding documents covering traffic and conversion, logistics, and the projects we'd be tackling, as well as a list of resources. We went over that information in the first weekly call, and every intern had their first deliverable completed within a few days.


Working at PK&C as a WINtern was designed to feel like working on a class project.

We started each week with a call on Saturday. Everyone demoed something they built the previous week, we had a standup, and then I gave a lecture on some topic like employment contracts or salary negotiations. Beyond that, the jobs were part-time and asynchronous, though I was usually available for real-time pairing on anything they were working on.

Project Person Purpose
PK&C Brand Identity Jeev Conversion
whopaystechnicalwriters.com Jeev Traffic
Podcast Booking Hallie Traffic
Professor Outreach Hallie Research
Copy Improvements Eva Conversion
New Content Drafting Eva Research
Client Project Michael Client

For the three new interns, I made sure they had at least 2 projects each, so that if they were stuck (or blocked by me not getting to something) on one they could move to the other.

Assigning and refining projects was one of the most interesting parts of the internship. I was able to work with everyone individually to create work that they would find interesting and fulfilling that would also advance a business goal. By tailoring projects to each individual's skills and interests, I was able to get their best work.


Here is a portfolio of what each intern accomplished.


Jeev created a bunch of original designs, a visual style guide, and proposed layout updates for my website. Some stuff is already live, others will be going live when I get them up, still more are held in reserve for improving Cold Email for Interesting People in March.

Sample of Jeev's Designs

Jeev also worked on a new version of Who Pays Technical Writers. We'll launch the full site a few days, but for now check out this early mockup he made.

WPTW mockup

On launch, the site will be open source, so you can take a look at his code then.


Hallie wrote well over 100 cold emails during her internship. This wasn't just copying and pasting a template, but researching the person she was writing to, adjusting prepared material to meet their interests, and adding genuine personalization.

First, she queried podcast hosts about having me on their show, leading to me being featured on Indie Bites, 10 Minute Tech Comms, The Not-Boring Tech Writer, and Side Hustle School. These episodes will mostly be released in February, and each time an episode is released it generates a small traffic bump and exposes my work to a new audience.

Hallie also sent market research emails to professors at colleges and universities across America. Working from a list of professors, she sent personalized messages asking about their students' needs when learning writing. Already, several responses have given me direction for preparing a version of Writing for Software Developers aimed at the classroom.


Eva worked on a bunch of smaller projects and was involved in other interns' work as well, which makes her impact both large but difficult to measure.

Eva created:

  • New copy for my website, especially the Writing for Software Developers page
  • A style guide for PK&C
  • A bunch of feedback for CEfIP 2 for when I work on it in march
  • A user research email to send to CEfIP readers asking for feedback

I want to draw particular attention to another thing that Eva did: a beta test of the professor outreach project with Grinnell professors. She discovered that the entire motivation of the original outreach plan was flawed, and saved the project from generating a bunch of emails that would have been, at best, ignored. Her user research helped me adjust course on the project and re-imagine it as a user research project that has been much more useful.


Over winter break, Michael advanced to an important milestone in the documentation: internal circulation. We've been working together since June on this project, so he has been able to see the entire cycle of working with a client: initial scope and negotiations, working through the actual project, and now finishing up and securing delivery.


I asked each intern to prepare a short writeup of their experiences.


As a design/development intern at PK&C, I worked to craft a visual style guide, update existing design assets, and help relaunch the Who Pays Technical Writers website. My first task was to identify the core elements of the existing PK&C brand (for example, the logo and primary colors) and incorporate them into a well-organized style guide. The challenge here was to create a comprehensive visual style that communicated the PK&C brand regardless of context. Much of my previous design experience has focused on a single product (like a website, magazine, or poster) rather than a brand. Working for PK&C gave me an appreciation for design in context; everything I designed throughout the internship had to remain consistent with the style guide and fit seamlessly with other products.

Using the style guide as my only constraint, I then worked to fully redesign several of the PK&C graphics and illustrations, ranging from book covers to Twitter preview images to Youtube thumbnails. My favorite task was designing a new cover for Cold Email for Interesting People, which was a chance to really exercise my creative muscle. After initially fumbling with different concepts, I hopped on a call with Philip and was able to narrow in on what he was looking for. With a makeshift “mood board” of book covers in my head, I attacked the project with renewed vigor and designed a cover that Philip loved. With a more clearly defined aesthetic direction, I found it much easier to redesign the other PK&C assets.

My final project as a PK&C intern was to design and develop the frontend of Who Pays Technical Writers. The existing website was a simple Bootstrap site with a list of publications and agencies that hire technical writers. My job was to design a new and improved version with more detailed entries, search/sort features, pagination, and a form page for suggesting new resources. After creating a mockup and running it by Philip, I began writing the HTML, CSS, and JavaScript to make the new site interactive. In parallel, I worked with Philip to migrate the site to a new development environment, during which his help with build scripts and version-control was very helpful. As I write this, I'm working to finish developing the site in preparation for the launch.

As this internship comes to an end, I'm incredibly appreciative of the unique opportunity I had to work with a very small but well-rounded team. Throughout the process, I learned from Philip about how to build connections, seize opportunities, and navigate the business side of technology. I also loved the chance to work alongside three other interns, each of whom brought a different set of skills and talent. Seeing Hallie's dedication to get Philip on a podcast, Eva's detail-oriented approach to writing, and Michael's clever methods to syndicate content was a rewarding experience in itself. And, in the process, I developed new skills and did work that I can proudly display in my portfolio.


During the WINternship I had two main projects: professor outreach and podcast booking. The initial plan for professor outreach was to send cold emails to professors suggesting that they check out WfSD, possibly buying a license for their department or putting the book on their course syllabus. However, user testing revealed the problems with this plan, so now we are conducting market research to learn about CS students and their writing. With this information, Philip can develop an effective version of WfSD 2.0 tailored towards his goal audiences.

From this project, I learned about how to write cold emails. I learned what aspects should be included and how the emails should be structured. I also gained experience working in a team on this project by being able to have Eva look things over before Philip does, and coordinating between multiple people. Additionally, I learned how to change direction on a project that considerable time was already spent on.

I also spent some of my time working on booking Philip to be featured on multiple podcasts. In this project, I researched different shows to create a large list of possibilities and evaluated these shows based on specific characteristics (currently producing content, features guests, etc.). After finding the shows I wanted to contact, I made email templates for the different types of shows that I could tailor to each podcast. I went through the list and contacted the podcasts, sometimes digging deep for contact info. I added or deleted different content from the email (e.g., Gumroad, Philip's technical writing experience, previous feature on Software Engineering Radio, specifics for the success of WFSD) for each show based on what I believed they would be most interested in.

I really enjoyed the podcast booking project. Overall, I gained a lot of knowledge on the world of podcasts. I learned how to research shows to gain information so I could tailor the emails to best fit their needs. As I continued contacting the shows, I got more efficient at doing this and rewriting the email templates. With this skill, I can send a large volume of personalized emails. I also now feel very confident in my skill to successfully get a guest featured on a podcast. I may not use this specific skill in my future, but I still value having it, especially after learning how podcast appearances are a great marketing tool. Additionally, it felt great to see the concrete results of my efforts: successfully booking appearances! Not all projects yield such concrete results, and I now have numbers to advertise for future job searches.


My job as an editorial intern at PK&C this winter was to edit new and existing content produced by the Company. Over the course of my internship, I focused on contributing as much as I could to polishing text and advising structural changes to get our message across clearly and efficiently.

If I'm doing my job well, I'm invisible; my end goal is always to help the writer I'm working with to evolve their content into the best possible version we can create. This internship has given me a fantastic opportunity to practice that skill, working on customer-facing site pages, academic outreach campaigns, and even future editions of PK&C's flagship publications, Writing for Software Developers and Cold Email for Interesting People.

One of my favorite projects this winter was the campaign of cold emails to professors across the country that I worked on with Hallie. Hallie would write the initial copy of the emails and I'd add comments about what changes I'd suggest in structure and wording, and then we'd work together to get our respective visions to mesh. I also conducted a brief user study early in this project, sending a draft of the email to a few different Grinnell professors of similar profiles to the professors the email was actually intended for and asking for their feedback. Based on the feedback these professors gave, PK&C changed course on the project, resulting in a significant rewriting process for the email campaign. As in the first round of drafts, I worked closely with Hallie on developing clear and concise emails to send to the targeted professors.

In addition to this editing work, I also wrote the first iteration of the official PK&C style guide during my internship. Though this wasn't my first time working on a style guide, I'd never been the initiating editor creating the guide's original version. Using the Chicago Manual of Style, 16th and 17th edition, as the default style manual for the Company, I wrote and developed a PK&C-specific guide to cover frequently-asked usage questions, as well as more individualized standards for styling PK&C terms in publications and on the web.

One of my favorite things about working for PK&C this winter was that it gave me the chance to work in writing and editing, my own academic and professional area of interest, while also being exposed to the forward-thinking ideas and personas in the technology industry. As a company, PK&C blends these two elements seamlessly, and as a result I learned much more than I'd ever expected to about industry terms and practices. One incidence of this happened during the style guide project, where I created a simple edit log that Philip requested I change to a software-style semantic versioning record. At the time, I had only the vaguest idea of what semantic versioning was, and the pursuant research taught me a lot about shipping and updating processes in the software industry.

But even setting aside the excellent professional experience and portfolio pieces I gained during this internship, there was still much I enjoyed in the program - especially its interpersonal aspects. Through weekly meetings where the interns shared our progress and Philip advised us on important skills in the business and tech world, like salary negotiation and reading a contract, I learned not just within the scope of my own internship but within the others' as well. This has been an awesome experience, and I can't wait to see what PK&C does next!


As a PK&C employee, I work primarily on technical writing for a hardware company's documentation. The company creates a device to track hands. This device is fairly complex and uses cameras and LEDs to illuminate and photograph hands, after which the images are transferred to the computer and used to generate 3D models of the hands for interaction.

It was my job to elaborate on this process and explain the complex phenomena behind the device. To acquire this information, I interviewed the founder and CTO each week. Ultimately, my writing will allow for greater standardization across the industry and provide valuable insight into the device and the company behind it.

Under Philip's guidance, we organized the sections we'd written into a polished website. At this point in the process, the website is circulating internally and we will make modifications based on the user feedback we get.

I truly enjoy this work. I love learning about the clever tricks and optimizations the client has used to improve their design. Both the meetings I've had with the CTO and Philip have been incredibly valuable and have added to my knowledge of business and technology. I have greatly improved my technical writing and polished up my strategy for grassroots promotion. As I plan to own my own technology company in the future, I am honored to work with such impressive individuals and I am excited to present the work I do to the wider world.


I'm thrilled with the outcome of the internship. The only thing I wish I'd done differently is instead of using lowest-common-denominator tools like Google Drive, I should have asked everyone to learn my preferred toolkit, which has a low learning curve and accelerates productivity.

Next winter, I hope to host a similar program, and depending on the financial performance of my business I may be able to expand the program, make it full-time, or otherwise improve the quality of the experience. I also will look into running a summer internship this year if I can build and fund the right program. I hope to work with these people again in the future, but if you're reading this and are hiring you should hire them quick before I get the chance!