Scratching your entrepreneurial itch – Part 2

Photo of two males sitting and talking in a break-out area of a co-working space.

So you have an entrepreneurial itch? Here’s something that might help you with that.

This is Part 2 of a series of 3 articles: In Part 1, I introduced the notion of the entrepreneur and being entrepreneurial for yourself while being an employee of an organisation.

In this article (Part 2), let’s explore scratching your entrepreneurial itch by going to work in someone else’s start-up. You don’t have to take the big risk of starting something yourself: Not as the first step, or even any future step. [Sidenote: To be clear – a “start-up” is not simply a new business that is doing something well-known and established; it’s a highly evolving venture, typically tech-enabled, creating a new product or service that likely has a lot of risk and unknowns, expecting to scale-up from just a few people. And often it’s a small organisation that doesn’t have, nor seek, the maturity or infrastructure of established organisations.]

I’ve had the experience of working in a few other people’s start-ups. I’ve recruited and inducted other people to work in those start-ups. And I know people who have launched their own start-ups who have shared their thoughts for effective colleagues/collaborators. We’ve got some useful things to share from real-world experience.

[Another sidenote: In terms of Self unLimited Scenarios – if that’s on your mind – you could be in Scenario 2, where you are happy with your main current employment job and want to add something on the side (part-time) as you expand your abilities and reputation. Or you could be in Scenario 3, where you are unhappy with your main job and are actively exploring how and where you will go join another organisation that will work with you to have the kind of workscape you want.]


Start attending to your entrepreneurial itch

Here’s some steps to take in your adventure to work in someone else’s start-up venture.

  • Decide how committed you are to work with a start-up. Is this a casual or a dedicated interest? Will this be something you will do on the side as part-time work; or are you prepared for the sacrifices that come with working in start-up organisations? Because active fast-growing start-ups will likely want a lot of your time, attention and energy – working in them is not for the leisurely.
  • Reflect on what kind of entrepreneur you might be and what size of organisation is a good fit. Use this quiz as a prompter for your thinking. IMPORTANT – You don’t have to accept the results as True with a capital T. Treat them simply as a stimulus for thinking and experimenting. Turn up your curiosity radar.
  • If you lack opportunities for getting foundational experience, then do a small side-gig to show yourself to be a self-starter (like described in Part 1 article). Or be an intrapreneur with a volunteer organisation (more on intrepreneurship in the third article to come).
  • Do your Value Exchange Ledger for working in a start-up organisation (buy the deck of VX cards from our shop and/or do our short eLearning program). Think about a real organisation that you know about to give you rich context to explore value possibilities, or be more general as a starting point – you can always review and refine your Ledger as you get to know more about any particular organisation. A symbiotic value exchange is a great thing to aim for.
  • Do your unique Value Proposition for a start-up eco-system. Use the Value Proposition Canvas tool by Strategyzer, and draw upon the Value Elements you put on the IN side of your VX ledger – see previous point). The VPC is a tool many contemporary start-ups use, and it’s great for you to be familiar, even fluent in defining a Value Proposition. Once you have this defined, collect and curate artefacts, stories and recommendations to show the substance of what you offer. Be ready to refer to these, or showcase these when networking and interviews.
  • Treat your attending-to-this-itch like your own project/venture. Be prepared to invest in yourself with money and strategic activity to prepare yourself and to introduce yourself to entrepreneurs. (See point below about Pitching.)
  • Find yourself a peer-mentor or sponsor for this venture to encourage and validate you. This won’t be like normal job hunting and you need support to ignore certain voices that might caution you to make ‘safer choices’.
  • Intentionally create a diverse professional village for your own venture – filled with people who can inspire and challenge you. Who do you know already? Who knows people to introduce you to? What kinds of people would be good to add?
  • Learn about what’s happening in entrepreneurial eco-systems.
    • Follow entrepreneurs on social media – go for well-known names like Richard Branson, as well as the lesser known ones who still have an impact like Kate Kendall and David Hauser (Australia-based). Contribute to their conversations, amplify messages you believe to be helpful to them.
    • Join communities like Silicon Beach (you’ll get to meet David H there at Melbourne events). Check out local Meetups that have a innovation/start-up/lean flavour. Be interested and be interesting! Build relationships.
    • Subscribe to startup-innovation-entrepreneurial newsletters, magazines and podcasts. Learn the lingo. Get conversant in the trends. See who the players are, particularly local players in your area. Your Local Government Authority likely has a start-up supporting program – investigate what they provide and how you can tap into their support system.
    • Go to innovation exhibitions/expos/conferences where start-up businesses are going to get knowledge and support for their ventures. Talk with people working in start-ups and ask their advice. Find start-ups you want to be a fan or groupie of and join their communities – they’ll love your support, and may even have opportunities for you to be an influencer or early tester of their products and services.
  • Contribute financially to someone’s venture to show yourself to be an investor and willing to actively support other’s entrepreneurial endeavours. Check out crowdfunding sites like Pozible (I know the founder, and was part of their early-adopter  group in their early days). Or loan your money to small businesses through Kiva – the world’s first online lending platform. Experience the process and opportunity of being a funding investor.
  • Research the wording and skills mentioned in startup job adverts  … any advert! Don’t limit yourself to roles you would apply for. Build up a clear picture of how working in start-ups is different then established organisations.
  • Draft content for a Portfolio Resume (PDF with instructions of how to create) of the range of skills and experience that you think would interest a start-up business (and you’ll have a good idea of what this is, because you’ve been exploring the broader entrepreneurial eco-system!). Consider transferable skills. Ask someone who works in a startup to look at your draft resume, and advise how to strengthen this content for a start-up audience.
  • Do targeted responses to job adverts fully armed with knowledge about the organisation about self and why it’s a good match. Could do this just for fun and practice, as well as testing the waters about what’s currently out there.
  • Be creative for a start-up you really like, and prepare a pitch: a) Pitch their offering to someone you know, a potential customer; or b) Pitch yourself. Being able to do a strong tight pitch is a necessary skill when entrepreneuring. It takes time to develop this skill and you will want to be good at pitching yourself if you are seeking work. Pitching takes preparation, and with greater skill you can get quicker at the preparation part. Many innovation meet-ups or groups have pitch nights – a chance to have a real experience in front of a live audience, and get helpful feedback to improve.


And some additional thoughts from two serial entrepreneurs in my network.

Neville Christie (81 years young, entrepreneuring since he was 12!):

“I want to be able to read something about a person before I consider having them contribute to my business. A good online profile will do, it doesn’t need to be a resume. If a person is offering a particular skill or service, I connect more with profiles that are client oriented – which means they seek to understand their client’s needs rather than simply selling.
I’ll often seek out Freelancers for small creative and technological tasks – reaching them through platforms like Fiverr or Upwork. I’m willing to give them a go at responding to my brief with a basic offering. I’m prepared to have three iterations in getting the value I want – but after that I give up.”


David Hauser, Director and CEO of Silicon Beach Australia (I’ve summarised-paraphrased his thoughts here from a phone conversation we had):

  • Believe in the vision of the start-up you join, in what the start-up seeks to create or change in the world. Support this vision. Connect your personal motivation to realising this vision, such that you can work independently, self-driven and not need to be highly-managed or motivated by a leader.
  • Be able to speak-up and speak out quickly – even to people you think may be senior or more experienced. Take the lead when there is an issue to deal with, or a job to be done. Call out what might be wrong and not working. Everyone has a perspective that could make a useful difference – and this might feel like arguments in the intense context of startups. Appreciate the stress that creative conflict brings, and be able to recover quickly from this. And when a decision is made, get behind it regardless of your initial perspective: “Disagree and commit.
  • Expect your team mates to be sources of inspiration; as you can be to them. Be curious. Be aware. Learn about solutions they have come up with. And then take action to try something yourself that moves things forward. You need to be able deliver something, knowing it will go through iteractions to get better and change with the influence of your team mates. Underlying this is the need to be a really effective communicator with your team mates.
  • Add to your specialist skills, a range of general skills so you can contribute in multiple ways in a tightly-coupled team working under intense pressure. Be prepared to take responsibility and lead in your subject-matter-expertise as one of your key contributions to the team.


Working in a startup is for those who can work without predictable structure and routine. You’ll likely revel in the inherent uncertainties and have good tolerance for the inevitable inconveniences that arise. It can be a fun and exhausting ride. It’s worth trying at least once, thinking of it as an experiment (you can read a story of when I once worked in a startup). And if the entrepreneurial itch doesn’t go away – then employment in start-ups could be a more permament fixture in your workscape.


Up next: Part 3, being an intrapreneur inside an organisation where you currently work.



Helen Palmer, Founder of Self unLimited, has been in many workscape situations where she felt the entrepreneurial itch and did something about it. From small things inside an organisation, to working in other’s startups, to founding her own business and creating unique products and services – she’s got personal experience in activating and cultivating her entrepreneurial capability. She’s keen to help others take their first steps into unleashing their creativity and ideas for a world that needs them!



(Amended) Photo by Helena Lopes on Unsplash