How To Quit Your Job and Launch a Startup

Helpful tips on how to take a 100% pay cut to pursue your idea.

The biggest change in my career started with a presentation. A decade spent in digital media had me convinced that all big ideas are sold on slides. This story is about a few slides that carried an idea from my living room to Australia’s leading startup accelerator. For those that want to do the same, I’ve summarised tips in bullet points below.

TL;DR: My Advice for First-Time Founders (In Bullet Points)

  • It’s all about the pitch!
  • Pitch your idea like it’s a product, not an idea
  • Get ready to pitch without any visual aids
  • Get ready to pitch without IP protection; it’s the cost of doing business
  • Too much background reading may (probably will) complicate your pitch; spend the time getting customer feedback instead
  • Validation data is fuel, don’t let your engine run dry

The Problem

Process and productivity is a preoccupation of mine; but not the ‘list keeping’ style of self-sufficiency. I’m fascinated by the intersections of workflow. Below are a few questions that have often kept me from being, well productive.

  • After a document draft passes between authors; which version of the truth remains for the final copy?
  • A team finishes a brainstorm; are tasks allocated by capability, capacity or participation in the meeting itself?
  • What impacts the life expectancy of a new idea more; the presentation, presenter or approver?

At these intersections, you may sense some unspoken influence. Slight of hand steps in to shift the how while the focus is on the what.

It’s easy to measure workflow effectiveness; I want to know if work gives people what they want.

An Inception

30-Jan, 2012: Author Ryan Lizza of The New Yorker published a review of hundreds of pages of internal White House memos. Buried with the comprehensive evaluation of President Obama’s first three years in office I found inspiration.

Journalist Ryan Lizza of the New Yorker (*not actually Ryan Lizza)

Lizza detailed decision memos used by the administration to reduce complex policy matters to a single summary and set of options. Proposals that sustain, and record, momentum. These two paragraphs planted… an idea.

Each night, an Obama aide hands the President a binder of documents to review. After his wife goes to bed, at around ten, Obama works in his study, the Treaty Room, on the second floor of the White House residence. President Bush preferred oral briefings; Obama likes his advice in writing. He marks up the decision memos and briefing materials with notes and questions in his neat cursive handwriting. In the morning, each document is returned to his staff secretary. She dates and stamps it — “Back from the OVAL” — and often e-mails an index of the President’s handwritten notes to the relevant senior staff and their assistants. A single Presidential comment might change a legislative strategy, kill the proposal of a well-meaning adviser, or initiate a bureaucratic process to answer a Presidential question.
If the document is a decision memo, its author usually includes [three options: “Agree,” “Disagree,” “Let’s Discuss”] for Obama to check at the end. The formatting is simple, but the decisions are not. As Obama told the Times, early in his first term, Presidents are rarely called on to make the easy choices. “Somebody noted to me that by the time something reaches my desk, that means it’s really hard,” he said. “Because if it were easy, somebody else would have made the decision and somebody else would have solved it.”

Since learning about that process, each working day served to validate the idea further. I witnessed deliberations over email or in meetings focussed on what to decide — how to decide was an occasional afterthought. By 2015, the idea was a happy place I’d regularly visit when reflecting on challenges at work. A sketch formed in my mind; an app that I would build.

Pitch, Pitch & Pitch Again

One weekend my wife Robyn and I took our children to the zoo; the trip was an opportunity to reflect. On the drive home, I spoke up for the first time. Without going into detail, I told my wife Robyn what I was thinking and feeling. To give her, and the idea, a more robust narrative than the car trip allowed I booked time in our shared calendar for a presentation. That diary date was the first milestone.

30-June, 2015: I prepared the living room for a significant audience of one. Using AirPlay, I sent the Keynote file from my Macbook to Apple TV. The Keynote iPhone app let me change slides with the swipe of a thumb. I could focus on my voice and gestures. Kind of like Steve Jobs. I’m kidding. But really.

Slides transitioned across our TV as I began with the problem statement and my inspiration as noted above. Then I revealed some mockups of an iOS app. The concept was clearly at early stages, and I outlined the plan to pursue development… full time. I stressed ‘early stages’ and tried to play down the ‘quit my job’ part. An unfortunate combination of ideas to sell, but she saw the vision and my passion. With her support established, I set my sights on tweaking the content for the next stakeholders.

01-Aug, 2015: My family has supported me at every turn in my life; I’m incredibly fortunate. I knew support would be there again for me this time, and I was looking forward to more feedback. On an interstate trip, I presented to my mother and brother in Sydney.

With no Apple TV at Mum’s house, I cobbled together some adaptors to connect to the TV using VGA. Yes, VGA. At first, it didn’t look like the vision would be clear. Before reaching for the bounded print outs, I ran a lifeline search on Google. With a brief adjustment to the underscan slider in Macbook display preferences, it was game on.

Their feedback highlighted something I hadn’t anticipated but seemed obvious. I had over complicated the proposition. Revisiting the concept so often since reading the New Yorker article led me down many avenues to understand and define the value. Research papers on decision fatigue. Countless articles on organisational behaviour. By seeking to justify the proposition, and it’s extensions, I’d managed to sell the steak, not the sizzle.

So, the challenge was to make the proposition simpler. Before I’d solved it, though, I threw in another variable: IP disclosure. I wanted a non-disclosure agreement ready before gathering further feedback. My brother kindly prepared a document for me. I setup an account with hellosign.com to send and track NDA signatures ahead of meetings. Now the proposition had to be simple yet secret.

22-Oct, 2015: I organised a time to soundboard the idea with my friend sam granleese. I was lucky to have worked with Sam at carsales; he’s the best strategist I know. Over coffee, he’s decoded many business moves, shared insider views on digital trends and recommended tools and tactics to unlock value from data.

I’d asked ahead of the meeting if he’d agreed to an NDA and he didn’t mind. He diligently read the agreement and gave me candid feedback on the process of asking. He saw use cases for the process that I hadn’t considered. Of note, he identified that an agile workflow was great for engineers but, at times, a mystery for stakeholders. The app could help product managers quickly liaise with stakeholders on changes, approvals, clarifications or requests needed for development as it happens.

23-Oct, 2015: The following afternoon I enjoyed a beer with Lyndon Gee. I first met Lyndon in my media agency days when he was working at AOL. I later learned that he was a good friend of Robyn. He’s launched startups in London and Australia; I knew his view would be invaluable.

Lyndon gave me alternative roads to market that I hadn’t considered. Different platforms, pricing and messaging. In fact, the use case suggestions from Sam and Lyndon were excellent. They stretched my thinking about the customer and gave me options. At the time I was reading The Lean Startup by Eric Ries. Defining the early adopter set would require experimentation and having options didn’t deter me from moving forward.

With further amendments to the presentation, I was ready to pitch to someone outside my comfort zone.

Picking a Partner

Updates featuring BlueChilli appeared in my Twitter feed frequently, and their model was attractive to me. The leading Australian startup accelerator is clear about where they sit in the range of development options, the Goldilocks Zone as illustrated below. In one chart they managed to answer my concerns about technical co-founders and an agency approach:

After reaching out through their site, I was in contact with Ren Butler, and we arranged a meeting. I still wanted to protect the IP so offered to send Ren my NDA. She was gracious in declining to sign, and her reasons made sense:

We don’t sign non-disclosure agreements for initial meetings like these as they are just about getting to know one another and the initial pitch (an early stage sales pitch, more like you would a potential new customer).

Further to that, she shared a link to an article from startup magazine Anhill Online, which illustrates the other side of the NDA equation. In short, NDA’s don’t work for frequent investors.

Sharing information in one meeting without an NDA effectively voided all NDA’s I’d arranged to date. So, to grow I would need to take the conversation public. I resolved to move forward without an NDA, aided by the following rationale:

  • Pursuing IP infringements would be uncertain and costly, even with an NDA in place
  • Beyond some basic branding, there was little to protect
  • Gathering feedback and insights would be far easier without protections
  • Prospects of growth were much better through content marketing compared to stealth development with a ‘big’ launch

06-Nov, 2015: I’ve presented a lot through my career, the difference here was how aligned I was to what I was selling. The outcome of these meetings with BlueChilli could have a big impact on my world. Luckily, Ren was super easy to talk to and clearly right on the pulse of what founders like me are thinking. She was quick with a few jokes that put me at ease — I felt overdressed until she made a joke about startup chic meaning you wear whatever you want. With my MacBook open I began turning through the slides of my pitch.

Having read a few of her blogs and I personalised the content to include a quote from her which got a laugh. The material was still dense with research references, but it had flow. Her feedback “I’d sign up for your beta!” gave me a huge lift. This line was a major turning point in my thinking. I wasn’t pitching an idea — I was pitching a product.

Ren gave me the rundown on how they work with founders. The next step was to complete the BlueChilli ‘Pitch To Us’ Form — the formal gateway to a meeting with Joe Keiley.

Pitching for Keeps

17-Nov, 2015: While all the pitches I’d done so far were important, this one had a binary outcome. I searched for some information on Joe and found some articles. His title is ‘Pitch Analyst’ and I calculated that he received somewhere from 4 to 6 startup pitches per working day. Wow, that’s a lot.

Joe was friendly and brief. Although I had booked a 30-minute meeting, I sensed it could be over in 15. On the way to the conference room I mentioned I had only a few slides; his response meant I was immediately unprepared.

I don’t really do slides, let’s just talk.

It was a setback, but I resolved to tap dance my way through. The focus of Joe’s enquiry wasn’t on the product; it was on me. His first question was about motivation, something I hadn’t articulated in an interview like this before. The upside of being unprepared is that you’re responses are authentic.

I got some key points across through the interview, but two areas needed work — the customer definition and the revenue model. Joe gave me some homework: validate the idea with real feedback and return next month with the answers.

15-Dec, 2015: Joe flew down from Sydney again, and I talked through my research results. Customers felt the problem and identified with the solution, but questions still hung over the product.

People may say they like the idea but would user adoption set in long-term? Adoption is the big unknown with group productivity products. Without usage data, it was tough to argue the app would be anything more than the flavour of the month.

Still, this is what the BlueChilli program is about — validating so you can take the smart risks. I’d demonstrated to Joe that I had enough gumption to get 30 people to fill out my survey — enough data ‘fuel’ to keep the conversation going.

19-Jan, 2016: Joe asked me to come back in and meet BlueChilli business adviser PK Rasam. PK has excellent startup experience, currently on his third, with a background in management consulting to boot. In this pitch, I included slides with the new research and even a video I’d prepared.

There were still gaps in the addressable audience and business model. I was sure I hadn’t cleared all the hurdles. I went home and had Neapolitan ice cream.

Joe emailed me the following day with a term sheet; I had made it. Those months of work had paid off, and now I could proceed with the accelerator program to learn, refine and execute the product.

So that’s the story of the first few, by no means the last, hurdles and triumphs of my journey startup land. It’s also my first post on Medium so if you’ve made it this far please validate it with some hearts, comments or questions below!