👋 Howdy! This is the Open Source CEO, the bi-weekly newsletter that unlocks your full potential.

COMING IN HOT TODAY 🔥 

🌱 Early stage founder, doing great thing: Our Ajay Prakash interview.
🧵 Up your money wisdom: In a single thread.
🎙️ An audio education: Out: university. In: podcasting.

If you’re interested in sponsoring these emails, reach out. I’d love to share some ideas and see how we can work together.

PARTNERS 💫 

LEADER OF THE WEEK 🎙

We have a great one for you today team. EntryLevel, founded and led by Ajay Prakash are a very early-stage startup but one that is off to a flying start. They are backed by Blackbird, one of the best VC firms in the world and are tackling a huge and meaningful problem.

Let’s hear from Ajay and see where the secret sauce is coming from.

Ajay Prakash - Founder & CEO of EntryLevel

Ajay is the Founder and CEO of EntryLevel a tech education company that is making cohort based education accessible to all without the $10,000+ price tag. EntryLevel is 2.5 years old and has already reskilling over 30,000 people in 182 countries and is growing faster than ever.

Prior to EntryLevel, Ajay ran a non profit called Real Skills in the education sector, helping engineers find employment after university. Real Skills helped over 5000 people. He was also the co-founder of several failed startups such as Tailor Brews (online custom beer brewing), Qubit Protocol (a quantum computing company) and a litany of others. Each failure was bigger and more spectacular over time, growing products to millions in revenue and hundreds of thousands of users.

Ajay has years of experience in growth and product as the Global Head of Product at Draper Startup House (a hospitality company for entrepreneurs with locations in dozens of countries), Chief Product Officer at Tradeflow (a large software company dedicated to international trade), and many other roles.

What is your main day to day job as CEO?

Since we’re still a relatively small company, I think it’s important that I’m still in the trenches doing individual contributor work - building programs, designing product features, and executing on ideas.

In terms of structure, I have 1on1s with my direct reports every Monday which discuss goals, how they are feeling, and anything I can unblock them with. Apart from that, we have a strategy session every Monday where we check in our OKRs and see how everyone is doing. Mondays generally is packed with meetings for me. Tuesday to Friday, I split my time with the following:

• 20% - Unblocking my team with various things

• 20% - Reviewing and providing feedback on work

• 40% - Actual work such as building programs, product development, and more recently customer support. (I’ve seen tremendous benefits of hopping on support myself)

• 10% - Meetings (partnerships, hiring, or otherwise)

• 10% - Research and opportunistic work. Looking at the sector, markets, and just various study

Explain your philosophy around leadership? How do you think about it?

I’ve always liked Quiet Leadership by David Rock which is a leadership style that plays more of a coaching role and helps people come to their own decisions. My grandfather always told the story of Archimedes who sat in a tub and noticed the water rise, discovering the law of buoyancy. According to him, Archimedes was so excited he ran down the streets naked to announce his discovery yelling “Eureka!” There’s the power to decide something yourself. So as much as possible, I want my team to discover what they should do themselves rather than me telling them.

I’ve tried to create more of an idea of meritocracy by being receptive to ideas from all levels of our organisation to the point where I have many non-direct reports sending me essays with amazing ideas or thoughts almost weekly (and I love it!).

How do you build culture?

We want to build a supportive culture that is focused around helping everyone work on OKRs without micromanaging them. Here’s what we’ve tried to make that happen:

• Taco Leaderboard: When we tried to do a ‘kudos’ initiatives where team members can give each other appreciation for their work or help - it was hard to enforce it. However, we discovered the easiest possible way of doing it was “Tacos on Slack” and just getting key team members to religiously do it. The rest of the team followed, and now it’s normalised.

• Customer Wins: One of the things I noticed was just how much love we get in socials and online. I wanted the product and development teams (who primarily just see issues and problems all day) to really see these wins as well. So we have a Slack channel for this and also discuss it every Monday. It helps humanise some of the goals we have around growth or student completions.

• Friday Townhalls: Every Friday, every team member comes together and we play games or discuss anything we’d like. It’s more of an informal session for the team to bond with each other. It’s always tricky to maintain relationships in remote working so we use Friday meetings as an opportunity to do this

• Wednesday Virtual Co-working: A recent addition where we just work together on a Google Hangouts link where interruptions and chit chat are encouraged.

To be honest, we haven’t figured this out perfectly. We’re always trying new things and looking to improve our culture but these are some things that have worked reasonably well.

Detail your recruitment strategy. How do you hire all-star talent?

You want to hire the best, but as a startup, there are really two ways you can approach this.

A) Convince A Players to join you and take a risk with you

B) Find diamonds in the rough who you’re sure will become A players and you can get them whilst they’re cheap

Earlier in the organisation, I focused on (B) by hiring quickly and giving them 1-2 month trial periods to see how they go. Incremental commitments. I’ll give them projects to work and as they succeed, I ramp it up. However, as we grow, I’m pitching more serious players to come to work with us. Success begets success - I’m motivated to keep crushing it so more people are attracted to come to join us. The best players are attracted to other A players and A-class companies. So I’ve strived to just make us a leading A-class company.

How do you set goals?

We used the OKR model which has been helpful, especially in 2023. We used to have OKRs across the organisation and for each department but it kept breaking down. This year we’ve just only set global OKRs and focused on 1-2 objectives which have been incredibly helpful in focusing us as a team. Being able to link things such as customer support to company growth has helped everyone have a better “why” when doing things.

For next quarter, I’ve done a brainstorming with these questions:

• What are the most important things that we need to get done?

• What do we need to start doing or changing?

• What do we need to stop doing?

Usually, the team and I have a dozen ideas or so then we try to prioritise and group these things to form 1-2 objectives. In the past, operations, customer support, and engineering have been tricky to loop into high-level objectives but we’ve been better at this by just being clear about how it impacts something like user experience or growth.

Do you run hybrid, on-site or remote and why?

We are 100% remote but we have a cluster of team members in Sydney, Australia who meet occasionally for dinner. We’re remote because it’s more effective for us as a company that has customers in 182 countries to cover multiple time zones whilst also not limiting amazing talent by geographic bounds.

How do you get the best out of yourself professionally?

Adding structure to my life helps me produce better work. As an entrepreneur, it’s tempting to craft your life to be flexible, but I feel for me it creates a lack of motivation and energy. I like waking up early and following a rough guideline for the week.

Ensuring I plan my week on a Monday means I can just focus on the work rather than worry about what I should be doing. 

EXTRA READING: Beehiiv recently profiled EntryLevel’s newsletter which has grown from 0>60k in less than a year! Talk about building a community!

And another quick piece is Ajay’s breakdown of getting 7000+ Signups in 7 days with $0 in marketing.

And that's it! You can follow Ajay here and also don’t forget to check out EntryLevel (and maybe sign up for a course!).

TWEET OF THE WEEK 🐣

TOOLS & RESOURCES 🔥

One, let’s call it a resource I have been enjoying lately is the Acquired podcast. Ben and David the hosts are two super smart guys and embark on what I would say are the best business deep-dives out there.

It’s not banter from start to finish, but it’s smooooth and I leave every episode (or series) feel like I am wiser as a founder.

You can’t go wrong with these guys. Check them out!

And that’s it! Feel free to reply to this email and spill your thoughts in a deeper more personal way as I'd love to hear what you thought of this edition.

See you next week. ✌️