Starting a Side Hustle: A Job Board for Venture Studios

Niche job boards can be good businesses, but they take a lot to build up. Follow the journey. (#74)

After writing about how to find a job at a venture studio and talking with numerous job seekers and venture studios I decided to launch a side project: Jobs @ Venture Studios.

Jobs @ Venture Studios is a niche job board dedicated to roles at venture studios (and venture builders / startup studios). It will also include jobs at studios’ portfolio companies.

Why am I doing this?

1. It’s an interesting experiment: I want to see if a niche job board for venture studios is a sustainable endeavour. There are a lot of underlying assumptions that will need to get validated. I think of this as an experiment, with an opportunity to iterate & learn actively. It’s fun / interesting to try new tools, techniques, etc. and keep my “building skills” sharp.

2. For the venture studio community: I want to support the venture studio ecosystem, which I do through content (here’s everything I’ve written about venture studios so far), podcasts, networking, etc. I believe strongly in the potential of venture studios, and we’re just at the beginning of the model taking shape.

3. To build in public and share the journey: I’m going to document the process and see if it helps others who are looking to create side hustles/projects. I intend to go through many of the fundamental steps of validating assumptions, iterating rapidly through build → measure → learn cycles and sharing results.

Step 1: Decide to Launch a Job Board

This step was fairly easy. Admittedly, I didn’t do an enormous amount of validation, but I knew that launching a job board through a 3rd party software product would be easy.

• I had 5+ conversations with job seekers interested in venture studios. This leads to the assumption that: “There will be strong and increasing demand from job seekers to work at venture studios and their portfolio companies.”

• Others in the venture studio ecosystem (such as Dianna Lesage) are featuring jobs in newsletters, etc., which suggests there’s interest.

Instead of doing rigorous user/customer validation, I decided to launch and experiment from there. I probably should have done more user/customer interviews to really assess demand, validate pricing, acquire early customers, etc.

It’s entirely possible I invalidate the need/interest in a niche job board for venture studios and I’m prepared for that (although I’ll be disappointed!) I’m giving myself 3 months to see if I can build it into a sustainable side business.

Follow Along: My Assumption Tracking

Eating my own dog food (or as we used to say at Salesforce, “drinking my own champagne” I’ve set up an Assumption Tracker using my template. You can track my priority assumptions there and how I plan to experiment against them.

Step 2: Pick a Software Tool

I did this very quickly. I Google’d “best job board software” and a few other search terms. There are lots of options. I picked jBoard because it looked simple and reasonably priced.

With minimal validation done beforehand, I didn’t have a prioritized list of feature requirements. I knew I wanted it to be easy (no code) and have the basic capabilities of a job board.

jBoard was incredibly easy to setup. I did it in less than a day and was live (Sunday, June 26th).

I did not put a lot of thought into the URL, but decided to go for a .com (venturestudiojobs was taken) and found one that was clear and literal: jobsatventurestudios.com.

There is a risk that I discover user/customer needs that aren’t possible with jBoard and/or I want to switch for other reasons. If that happens, I’d have to transfer everything to a new software platform, which would be a pain in the ass. Hopefully that doesn’t happen.

Step 3: Implement the Job Board

Once jBoard was selected, I built the job board.

• Basic configuration: This was fairly easy, there are only a handful of key settings in jBoard. I made the decision not to accept applications on the site, but instead point people to the original job postings. The risk is that it becomes difficult to get attribution (i.e. it won’t always be possible for employers to know where applicants came from), but I weighed that against giving venture studios another place to manage applications.

• Basic design: I went with a very simple “logo” and there’s minimal design elements in jBoard. There is a risk that the job board looks too vanilla, but it wasn’t a big enough risk to find something that gave me more design flexibility. Job boards are meant to be basic and functional. As long as it looks professional enough (which I suppose is an assumption!)

• Initial job inventory: I didn’t want to launch with an empty job board, so I used jBoard’s job aggregator feature to scrape jobs from a handful of venture studios. It worked for some, but not others. It allowed me to get ~80+ jobs onto the site on day 1.

• Set pricing: I decided to charge USD $25/job posting. This is very low. Most job boards will be in the $200+/posting range. But my job board has no meaningful traffic (yet) and I wanted to set the price low enough to encourage venture studios to try. Pricing so low may give employers the impression that the value is low, which is a risk. I do not intend to keep pricing that low, and in fact, I have a number of pricing experiments I want to run in the near future.

• Basic blog: Driving quality traffic to the job board is key to its success. Venture studios won’t post jobs on the site if there isn’t enough traffic. jBoard has blog functionality, so I wrote seven blog posts, and will continue to write 1-2 blog posts per week. The posts are written by ChatGPT (with minor edits). They’re not going to be the highest quality or the most unique, but we’ll see if they help the site get ranked. I do have a content strategy emerging.

• Set up analytics: I’ve set up Heap and Google Analytics to track the site. I don’t need two services, but I wanted to experiment with both. It’s been awhile since I used Google Analytics (when did it get so complicated?) I don’t think I need the best analytics tracking ever, just enough to measure traffic, where it’s coming from, and what it’s doing on the site.

Step 4: Launch the Job Board

The job board was live on May 26, 2024. It had ~80 jobs being aggregated from a handful of venture studios.

On Monday, May 27th, I posted on LinkedIn to connect with venture studios that are hiring. I didn’t mention the job board officially.

Although I had already decided to launch, I wanted to gauge interest and see if this led to any interesting conversations.

I got some positive reinforcement (always nice), although that doesn’t necessarily translate into customers!

From this LinkedIn post I got 3 direct leads, one of which converted and posted a job. 💰

The following day, I published a long LinkedIn post on how to get a job at a venture studio. This was written at the same time as my newsletter on the same topic (Tuesday, May 27th). In the LinkedIn post, I mentioned the job board:

The post received strong engagement (12k+ impressions, 45+ comments) and I posted the URL to the job board in a comment (and in several responses). I also responded directly to people who expressed interest. I don’t know if this post got me any customers, but I saw a number of job seekers visit the site and register for email notifications.

On Wednesday, May 28th, I posted on LinkedIn again, this time about questions that job seekers should ask venture studios and an announcement of the job board in a venture studio group. The latter post got 10k+ impressions, but only 2 comments and not as much engagement as I was expecting.

I also used X to announce the job board and posted a few times, but the audience there isn’t as strong.

Step 5: Market the Job Board

Once the job board was live I began marketing it. LinkedIn has been the primary channel, but I’ll explore others as well.

• I looked for job board directories (if you know any, let me know!) to add the board to. I found one, Jobboard Finder, but I haven’t gotten my profile published on there yet.

• I reached out to a number of people in the venture studio ecosystem to let them know I launched the job board. Hopefully they promote it through their channels. (Mixed results so far; possibly because I’m now competing with their own plans to launch a job board.)

• I’m doing a lot of direct outreach via LinkedIn. I’m finding venture studios through several online directories, and searching for “venture studio jobs” on Google. I go through each venture studio, see if they’re hiring for themselves, find the contact on LinkedIn and reach out.

Do things that don’t scale.

You’ve probably heard this many times. It makes sense, but it’s so tempting to try and automate everything early. I’m resisting the temptation to “build systems” and instead, I set daily goals for outreach on LinkedIn:

• On May 30th I reached out to 7 people

• On May 31st I reached out to 13 people

• On June 2nd I reached out to 4 people

• On June 3rd I reached out to 11 people

• Going forward I’ll aim to reach out to 5-10 people per day

In most cases I’m not directly connected, so I’m sending people InMail messages first. The response rate isn’t fantastic, so I’m shifting tactics: connecting first and then introducing the job board. Most people seem willing to connect on LinkedIn, but messages from strangers may not get a positive response.

I’m also going through everyone that liked or shared my LinkedIn posts, seeing if they run venture studios, and doing direct outreach.

I’m testing different messaging in my outreach, but not rigorously. I probably should, and measure results. It’s still early days though. Here are some examples:

Finally, I’ll continue writing blog content in an effort to build SEO for the site. I’m also testing whether employees at venture studios are interested in sharing their stories (i.e. “A day in the life of a venture studio employee”) because I think this would be unique and valuable content. One of the assumptions is that interviewees will share their interviews on social media, increasing the job board’s reach.

Other considerations:

• I’m not prepared to pay for ads (to attract employers or job seekers), but I may test that in the future

• I’ll continue to cross-promote the job board on Focused Chaos (although only a portion of my audience will be interested)

• I’m looking at other submission sites (like BetaList, ProductHunt, etc.) although I don’t think any of them are a great fit

• I’m going to start exploring Reddit (there’s some chatter on there re: venture studios) to see if it’s a good place to engage; maybe Quora too

• I’ll be exploring cross-promotions with others in the venture studio ecosystem

Progress So Far

As is often the case with new projects, the progress is so-so.

• I’ve had 2 employers pay for job postings. I was hoping for more at this point. Part of the challenge/risk is that venture studios may be getting enough applicants already. One person said, “We don’t really feel a need to pay for visibility right now with the amount of applicants we have been getting!” 😢

• Two employers stopped at the paywall, and one wants to pay via PayPal (which jBoard doesn’t support). I’m chasing down all three to see what can be done.

• Twenty people have signed up for job posting alerts. These are job seekers exploring venture studios. It’s early days, but I think this email list will become a key asset if this is going to work.

• Heap tells me there have been ~1025+ users that have visited the site since it launched (I setup Heap first, and Google Analytics a few days later). I don’t have a benchmark on expectations for traffic, but I would like to see it grow month over month at a significant rate. It’s early, but product and CEO-related jobs seem to be the most interesting to people.

My initial goal is to break even.

This won’t account for my time investment. 🤣

• jBoard = USD $225/month

• Google Workspace = USD $25/month

• Purchased the Global Venture Studio Database for USD $20

• Stripe fees (ongoing)

So my minimum monthly burn is USD $250, and I expect I’ll have a few additional expenses on top of that. Getting to breakeven means 10 job postings/month at USD $25/posting during this initial test period (excluding Stripe fees). That seems doable, but we’ll see.

Early learnings:

• Most venture studios aren’t hiring a lot of people. I already knew this was the case, but there’s also an explosion of venture studios emerging. We’ll see if that balances out. More established studios invest more heavily in recruiting for their portfolio companies. I’m not opposed to including portfolio company jobs (there are some already), but there are also many other job boards/job seeker resources for those jobs.

• Positive feedback doesn’t pay the bills. I knew this already, but just because someone says, “What a great idea!” or “This needs to exist!” doesn’t mean they’re paying you for anything. I appreciate the positive signals, but I’m laser focused on acquiring employers to pay and job seekers to engage.

• Launching makes things a lot more real. Everything becomes more intense as soon as you launch. The commitment level goes up 10x. Pre-launch, you can interview customers, do research and “take your time” validating. Your commitment level is fairly low and it’s easy to back out. Once you’ve built and launched something, it’s tougher psychologically to say, “that sucked, shut it down.” I have to stay aware of that and measure my overall time + financial commitment to the side hustle. On the positive side, launching makes the experimentation more realistic and meaningful.

• I hate “waiting around”. I’ll be honest—it’s been a week since I launched the job board, traction is less than I hoped, and I’m frustrated. The excitement of seeing an employer pay $25 for a job posting is huge…the waiting for others to do so is brutal. But you have to be patient. Run the experiments, put in the work, and don’t panic. I have to remind myself about that constantly.

Strategically there are lots of directions I can go in. I’m definitely thinking about all of them, but at the same time, staying on task and trying to validate my riskiest assumptions.

For example, I could make posting jobs free, try and get a much higher volume first and then monetize (i.e. premium job postings, employer profiles, etc.) The assumption here would be that more studios are willing to post for free, and the more jobs on the site, the more traffic / job seeker engagement we’ll get. The risk is that it delays monetization, and validating viability at all.

Another idea is to scrape as many jobs from companies’ websites as possible, drive traffic to them, and then reach out and say, “I sent you a bunch of applicants, isn’t that awesome? Now, it’d be great if you paid.” Scraping a lot of jobs will cost more money, so I’m not prepared to do that yet, and I don’t know how long it’ll take to demonstrate meaningful traffic + value. For now, I’ve opted to validate demand by seeing if any studio will pay $25 for a job posting—if I get enough evidence of that I may experiment with the business model to make it more scalable.

I’ll aim to do updates once per month through Focused Chaos on how Jobs @ Venture Studios is doing. Hopefully people find it helpful.

Wanna help and follow along?

1. Track my assumptions + experiments here.

2. Contact me if you have any interesting ideas / wanna help!

3. Employers at venture studios: post jobs! (If you want a bulk deal, reach out)

4. Candidates: visit the site and learn more about venture studios.

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