Ben Pecotich, Reflecting on 30 Years of My Startup Life

Text: Reflecting on 30 Years of My Startup Life

30 years ago I co-founded my first startup when I was 18… and I’ve co-founded over 20 startups and social enterprises since.

Some of them have been whole businesses, and others are products or extensions of Dynamic4. Some didn’t make it past the exploration and research stage, others went for years, and some are successful and still going.

In parallel, I’ve just clocked up 31 years working in financial services… and still going strong. This part of my life kicked off 24 May 1993 when I was 17. I shared that journey a few years ago in Ben Pecotich, Reflecting on 25 Years. Part 1: The Westpac Years (1993-1998), and last year in Ben Pecotich, Reflecting on 30 Years – The Pivot.

I feel lucky to have navigated the fun of 31 years of bringing together strategy, design, and tech to lead, design, and deliver strategic change in financial services in Australia, NZ, the UK, and Europe – and now 30 years founding startups/social enterprises.

These years have been full of learning, failing, iterating, and adapting. And still are.

In addition to my own direct experience, I’ve had the privilege of coaching hundreds of founders with our Jetpack incubator program, coaching clients and being a virtual CTO/CPO, university and high school student programs, and the many startup programs I’m a mentor with.

I also captured a lot of this experience in my book Solve Problems That Matter, which is a playbook guiding people to take a human-centred approach to design, build, and launch their idea.

I started writing a version of this reflection in January 2017, so I’ll pick that up again now and finish it…

How It All Began

I was in a meeting with a VC last week (January 2017) when the question of how many startups I’ve founded came up. I didn’t have an answer. As a rough guess I said probably over a dozen.

I’ve always been involved in business. Not necessarily big business but business in the sense of trade, of finding ways to create value someone is willing to pay for. Depending on your definition, I’ve always been an entrepreneur.

Entrepreneurship

Really? Well, I grew up in a hardworking trade family. Surrounded by and working with self-employed tradesmen. Tradespeople aren’t often thought of as entrepreneurs – it’s often not glamorous, definitely not by today’s measures.

If you accept the definition that an entrepreneur is “a person who sets up a business, taking on financial risks in the hope of making a profit”, then it’s hard to argue that self-employed tradespeople aren’t entrepreneurs.

From my earliest memories (the age of two), I was working with my dad – a brickie, and my grandpa – a metalworker. I was exposed to the way they built their brands and reputations, built relationships, worked with their clients to understand what they wanted, and designed solution concepts with them – and how they designed and built their products.

None of this was a one-time thing… it was constant and ongoing. In 2011 I wrote about my journey from being a brickie’s labourer and laying bricks to becoming a digital brickie. I’ve always been a designer and builder, motivated by the desire to deliver tangible improvements for people. I still am.

Despite heading into the corporate world within six months of leaving high school (after a brief stint in horticulture), a lifelong exposure to the small business and entrepreneurial way of life has shaped my story, what I value and how I see the world in terms of opportunities and risk.

What’s a Startup?

Every now and then, debates flair up about what a startup is. The actual definition is “the action or process of setting something in motion”… “a newly established business”. Within certain contexts only ideas that have the potential for massive high-leverage tech-enabled growth qualify for the term. This usually has an investment lens on it.

But I don’t subscribe to a belief in infinite growth – or that everything needs to scale.

I’ve co-founded a range of startups from physical product, service-based, community groups, and platform/app based digital products. I’m comfortable calling them all startups – using the real definition for all of them… in the early days of exploring a startup idea, you don’t yet know what it might be anyway.

The Catalogue

Here’s a catalogue and brief reflection on 30 years of my startup life. There have been a few more ideas that died out before the point of having a name.

You can skip my reminiscing on each startup and jump to what I’ve learnt

  1. Gangster Snowboards. 1994-1995. Physical Product Startup
  2. Dynamic4. 1 October 2001-ongoing. Leadership, Design & Innovation Services Social Enterprise & B Corp
  3. Dynamic4 Fitness. 2001-2005. Health & Fitness Services Business
  4. LIFE UK. 2003-2004. Social Media Tech Startup
  5. Hedge Fund Trading Platform. 2006-2008. Fintech Startup
  6. Timeseight. 2008-2010. Tech Startup
  7. Design for Meaning/Make Business Good. 2012-2013. Social Enterprise Collective/Co-op Project
  8. Good Local. 2012-2018. Collaborative Consumption Marketplace Tech Startup/Social Enterprise
  9. SuperPick. 2013-2014. Fintech Startup
  10. EventMojo. 2013-2018. Marketplace Tech Startup
  11. Jetpack. 2013-ongoing. Incubator for Early-Stage Social Enterprise Ideas
  12. Project X. 2013. Social Network Tech Startup
  13. Smart Locale. 2014-2017. Collective Impact Initiative
  14. Sydney Design Thinking (SydDT). 2015-ongoing. Design Community/Social Enterprise
  15. Value Machine. 2016-2017. Tech Startup/Social Enterprise
  16. Better Goals. 2016-2021. Disability Assistive Tech Startup/Social Enterprise
  17. Hero Investor. 2016-2017. Purpose-Driven Fintech Startup
  18. Ripple. 2017-2019. Tech Startup/Social Enterprise
  19. Climate Solutions Group. 2019-2020. Purpose-Driven Fintech Startup
  20. Social Enterprise Council of NSW & ACT (SECNA). 2019-ongoing. Social Enterprise Peak Body
  21. Solve Problems That Matter Book. 2021-ongoing. Physical & Digital Social Enterprise Product
  22. Interaction Week 2024 (IxD24). 2022-2023. Purpose-Driven Design Community

Gangster Snowboards

Co-founder & CTO with Brett Foster. Physical Product Startup
1994-1995 (age 18). Wellington, NZ

I was living in Wellington, NZ in 1994 and went to the annual snow show with a few mates. My memory on this is a little blurry but I ended up buying the Burton Brushie or a Nitro board. I remember having near instant buyer’s remorse though. I either sold the board or returned it.

One of my mates, Brett Foster – who was working in a skate and snowboarding shop (Wellington’s legendary 60CUBA) – came up with the idea of making our own boards. And so Gangster Snowboards was born.

We had the need and the idea. We had a distribution channel because Brett could sell our boards on consignment in the shop. We just needed to work out how to design and make our boards! Brett had the idea for the full-length base graphic inspired by the Marvel villain Kingpin. His school mate Karl did the original sketch… and Brett did the rest.

This is before the days of mainstream digital drawing products. Some words from Brett: “I added the finer details and finished up the line work. I then stretched it via a photocopier and tidied up the lines again. Then blew it up to full size and tidied up the lines again”.

The finished product was a monochrome line drawing of a 1920s gangster – wearing a trench coat and fedora, with a smoking gun hidden in a newspaper under his arm – finished with a red rose on the lapel.

Our topsheet design was very simple, black with our logo at the nose – a metallic silver sheriff’s badge with Gangster in a script font. One of our mates Justin Smith designed this, he’s an awesome graphic artist, and probably the most talented snowboarder and skater I ever rode with… and his parents owned a sign writing shop.

So we knew how it would look. Now we had to work out how to get it made. This became the first of many startups where I would play the role of CTO.

Luckily I found a company who manufactured custom snowboards. Working through technical details like length, width, shape, camber/rocker, flex, sidecut, and hole patterns – we got the spec of a board we wanted to ride. We agreed construction materials, graphics printing, and locked in a price. They agreed to a small run, and we’d have our boards early in the snow season.

I loved that board and rode it for several seasons. Brett and I basically got our boards for free, the price of selling a few others covering our costs.

Our costs were very high though, which meant our boards weren’t cheap. We’d met our own need but Gangster Snowboards as a business never really happened.

So many awesome memories flood back reflecting on this and looking at these photos. It was a fun experience and I learnt a lot. I wish I still had that board… and my old Airwalk Freeride boots, and my purple Quiksilver jumper… and my not yet blown out knee.

Dynamic4

Dynamic4 logo

Founder. Leadership, Design & Innovation Services Social Enterprise & B Corp
1 October 2001-ongoing (age 25). London, UK & Sydney, Australia

I started Dynamic4 in 2001 when I was living in London. From the beginning I designed it as a lifestyle business. The idea was it would be adaptable enough to encompass my endless curiosity and be the dynamic solution for my future as it evolved over time. The original legal name was Dynamic Future Solutions.

It’s done its job well and is still going strong over 22 years later. It’s evolved over the years. We always had a values filter but about 15 years ago it specifically became a purpose-driven business and social enterprise.

These days the primary focus is coaching, training, and working alongside leaders to solve problems that matter… to help accelerate the transition to more regenerative ways of living and doing business by using leadership, design, and innovation to help create the conditions for people and communities to be happier on a healthier planet.

I’ve shared the story of Dynamic4 and reflected on the journey many times. Dynamic & Adaptable. Dynamic4: The 20th Year includes the abridged origin story.

Startups have been part of Dynamic4 for a long time. Since 2013, we’ve committed a pool of at least 10% of our annual revenue to invest in actively supporting ideas for happier communities that are more empowered, inclusive, and regenerative.

We invest some of this pool in the form of grants through Dynamic4 Good, and some by taking an equity position through Dynamic4 Ventures.

Dynamic4 Fitness

Founder. Health & Fitness Services Business
2001-2005 (age 25). London, UK

Dynamic4 Fitness was a network of experienced health and fitness professionals. A collaborator model. My focus was to help our clients be fit for life with a strong emphasis on posture, strength, body awareness, breath control, and mental focus – to enhance both a sense of wellbeing and achievement.

I was lucky to study Pilates with Michael King from the Pilates Institute and became a member of the core team. I also worked with and learnt from other specialists in Yoga, Tai Chi, mindful meditation, physiotherapy, personal training, and sports therapy.

My two specialties were Spin and Pilates (group matwork, one to one, equipment, and pregnancy & Pilates). I taught at a range of health clubs, studios, apartment blocks, and offices – including the Pilates Institute, Complete Health Care Centre, Bow Quarter, Holmes Place Clubs, Fitness First, LA Fitness, YMCA, Interbrand, Deutsche Bank, and others.

I shared more of this story in Dynamic4: The Abridged Origin Story when I reflected on the first 20 years of Dynamic4 in 2021.

The essence of Dynamic4 Fitness lives on in the way we focus on integrating wellbeing into leadership, design, and innovation and is still core to what we do today.

LIFE UK

LIFE UK logo

Co-founder/joint venture with James Battison, Paul Russell & Alex Cambell. Social Media Tech Startup
2003-2004 (age 27). London, UK

A tech and mobile startup founded by James Battison. We met at an Adobe course, got talking about music, and quickly became mates.

James had been working on LIFE UK for a while, a celebrity and artist to fan social media startup – before social media was really a thing.

He asked me to get involved as a co-founder… and I roped in a mate Paul Russell, and Alex Cambell was in the mix too. We were all mates with a good mix of skills.

This was my first experience working for equity when I wasn’t an original founder. I still laugh when I stumble across my share certificate. A weirdly formal and ultimately meaningless artefact. We structured my involvement as a loose joint venture between Dynamic4 and LIFE UK.

We had some interesting adventures and deals that didn’t quite happen with Yasmin Le Bon, Models 1, Sophie Ellis-Bextor, and more. We were also shaping up an awesome project with Duran Duran when they didn’t have a label. They then signed a deal with Sony and our deal went away. They gave us VIP passes when they played Wembley Arena though, and we sat with Simon Le Bon’s mum and hung out in the green room.

We also worked with Skint Records (Fatboy Slim’s label) on mobile commerce in the days of ringtones and wallpapers.

Plenty of fun times and partying.

Hedge Fund Trading Platform

Co-founder & CTO with Ash Juneja. Fintech Startup
2006-2008 (age 30). London, UK

Ash brought a lot of experience as an investment banker and had access to capital. He had an idea for a hedge fund trading platform he wanted to design and build together. It sporadically made progress in the research stage but never eventuated.

I did design, build, and support a small trade floor for him and his brother though. Back in the days when the tech infrastructure was mostly onsite with limited cloud-based services for call recording and of course the Bloomberg terminals.

Timeseight

Timeseight logo

Co-founder & CTO with Michael Lifson & Brian Handisides. Tech Startup
2008-2010 (age 32). Sydney, Australia

Timeseight was a shared infrastructure and remote desktop startup. The vision was to provide our clients with reliable and secure integrated tech services so they can get on with their business.

Between Michael, Brian, and I, we had a huge amount of experience in tech infrastructure and IT service management.

The concept was a tech solution that allowed users to access their desktop, software, and files from anywhere at any time. We bought a couple of servers and I ran a bunch of proof of concept experiments with Citrix XenDesktop for desktop virtualization.

Technically we could do most of what we needed but the trend toward this model of access and support never really got traction. Part of this was more services and apps moved to the cloud and were accessible in browsers and on more mobile devices… and then the iPad.

We closed this one down cheaply and before we got to market.

Design for Meaning/Make Business Good

Co-founder with Anthony Quinn, Yummii Nguyen & Stephen Cox. Social Enterprise Collective/Co-op Project
2012-2013 (age 36). Sydney, Australia

Design for Meaning/Make Business Good was a little social enterprise collective/co-op project I started with Quinny, Yummii, and Coxy. A great bunch of friends and Westpac CX teammates.

We came together because we share a motivation to make a positive impact. We see social enterprise as a way to achieve that. Business that’s ethical, sustainable, and profitable but is focused on doing good. Prosperity that’s not measured in dollars but quality of life.

We decided on a two-pronged approach… doing the work of starting a social enterprise while sharing the realities of it. We’d transparently document the journey and what we learn – so we can share it with others to help them on their own social enterprise adventure.

I shared more about our approach in my 2012 post Design For Meaning: A Co-op Project For Positive Change.

These explorations resulted in Good Local and Jetpack… and ultimately my book Solve Problems That Matter: Design, Build & Launch Your Social Enterprise Idea.

Good Local

Founder. Collaborative Consumption Marketplace Tech Startup/Social Enterprise
2012-2018 (age 36). Sydney, Australia

The vision for Good Local was to make it easier for people to share and trade locally. To increase the awareness and adoption of local sharing and collaborative consumption services, providing an easy and compelling alternative to mindless consumption.

The ambition was to help people save money, space, carbon impact, packaging, and other waste by diverting waste from landfills, reducing greenhouse gas emissions, and encouraging behaviours like switching to renewable energy and water conservation.

The concept was to be like Airbnb for sharing services – a community and marketplace enabled by a digital platform to promote and map sharing services, making them easier to find and access.

I developed the concept as part of our 2012 Design for Meaning/Make Business Good collective and outlined it in Design For Meaning: Local Sharing Concept. I did a lot of research and built up a catalogue of existing sharing and collaborative consumption services, but I was working on a few other startup ideas at the time.

It was one of those ideas that nagged at me though and I kept tinkering with it for a few years. In 2015 I outlined the idea in more detail with the design of the brand personality in Good Local: Making it Easier for People to Share and Trade Locally.

I was unsuccessful in getting City of Sydney grant funding and shared my reflections on the crushing doubt in Good Local: Doubts. A story I know many founders can relate to.

At the time I was a regular guest speaker for every cohort of the General Assembly UX Design Immersive course. I brought a research brief to a couple of cohorts to dive deeper into attitudes and behaviours, which revealed similar insights to what I’d found from my own research.

In the end, the evidence overwhelming pointed to the reality that this landed in the aspirational behaviour category. I’m glad I resisted the urge to design and build the MVP platform.

It’s still an idea that nags at me and I’ve had conversations with a few other founders over the years who’ve had a similar idea… and shared all of our work on it in the hope they could do something with it. In 2018 I finally decided it was time to mothball it.

Sadly, every attempt I’ve seen at similar marketplaces have failed, or at best are zombie startups with a ghost town platform. If you reckon you can make it happen though, I’d share what I’ve got and cheer you on!

I explored Good Local as part of the Dynamic4 Ventures portfolio.

SuperPick

SuperPick logo

Co-founder & CTO with Dave Michayluk. Fintech Startup
2013-2014 (age 37). Sydney, Australia

SuperPick’s vision was to make superannuation simple and inexpensive for all Australians by helping people learn how to manage their super. Financial education with access to independent experts at set prices – with a strong focus on self-managed super.

I met Dave when he was part of the 2013 Founders Institute cohort and he asked me to come on as a co-founder and CTO. We made some progress but it never got to market in a meaningful way. It was also a lesson in getting shareholder agreements finalised and signed.

SuperPick was part of the Dynamic4 Ventures portfolio and Dynamic4 designed and built the website as the digital partner.

EventMojo

EventMojo logo

Co-founder & CTO with Sanjay Sundarjee. Marketplace Tech Startup
2013-2018 (age 38). Sydney, Australia

EventMojo was the one place you could find, book, and pay for all the products and services you need for your event. We also focused on building a community with great connections, articles, and guides to help get people inspired.

For event suppliers, we provided an online platform and service that enabled them to market their business – as well as their products, services, and packages – and to receive enquiries, bookings, and payments.

Sanjay had the idea and reached out to me to join him as a co-founder and CTO. My key focus areas were our strategy, design, product, and tech. Sanjay was the CEO and focused on funding and marketing.

We launched our platform at Inspire EX (formerly the Australian Business Events Expo and Sydney Event Showcase) with a booth and signed up loads of event suppliers. Our model was free listings and enquiries for suppliers, and they only paid a commission on actual sales.

A key differentiator at the time was that unlike other event directories that just listed suppliers, we listed the specific products, services, and packages that people hosting and attending events were looking for.

  • EventMojo at Inspire Ex

We got a bit of traction, especially with paid social and search, but we never had the funds to ramp up the marketing.

We featured in Startup Smart/Smart Company, Startup Daily, and strangely Business for Beginners in Canada. I also shared a bit about our approach in an interview with Sensis.

We had a couple of close calls raising capital but in the end it didn’t happen and we closed down after five years.

EventMojo was part of the Dynamic4 Ventures portfolio and Dynamic4 designed and built the platform as the digital partner.

Jetpack

Co-founder with Anthony Quinn. Incubator for Early-Stage Social Enterprise Ideas
2013-ongoing (age 37). Sydney, Australia

Jetpack is an incubator program for early-stage social enterprise ideas. We provide coaching and advice to help build momentum and move your social enterprise forward with confidence.

Quinny and I started running our first Jetpack and custom Jetpack sessions in 2014. At the time we were calling the program Cut to the Chase as a product of Value Machine, which was part of the Dynamic4 Ventures portfolio. In 2016 we renamed it to Jetpack for Changemakers when we refocused Value Machine to be a specific product. Not long after it became Dynamic4 Jetpack as a product of Dynamic4 rather than being a standalone social enterprise.

The program has grown and iterated over the years. It started with some in-person workshops, we then took it online as a chat based coaching program, and then brought back the workshops in a loose cohort format from 2017.

Throughout this time we designed and delivered custom Jetpack programs focused on working with one organisation at a time. Typically this would be an NFP who wanted to start a social enterprise product or service – or do some business model innovation – to diversify revenue streams and reduce reliance on grants and donations with earned income.

In 2019, we created Dynamic4 Thrive as a version of Jetpack to help NFPs create social enterprise products and services that deliver on their core purpose while generating sustainable earned income.

We’ve had the privilege of working with over 60 founders (80% female founders) from over 40 social enterprises/purpose-driven startups with our Jetpack and custom Jetpack programs.

This was the other key thing to come from our Design for Meaning/Make Business Good collective, which is where we developed the initial concept.

My book Solve Problems That Matter: Design, Build & Launch Your Social Enterprise Idea is an extension of this program in book format supported by a free healthcheck, downloadable worksheets, and other tools.

Jetpack and Thrive are currently delivered in the form of our 90-Day Coaching Program and custom innovation sprints.

Project X

Co-founder & CTO with Ren Becker. Social Network Tech Startup
2013 (age 37). Sydney, Australia

The vision for Project X was to make it easier to connect and get out and do things with your friends and contacts. The concept was to use the digital relationships and tools many of us already have – to share experiences in the physical world. Playing sport, going for a drink or meal, gigs… the experiences that make a life.

We were focused on the individual. Rather than connecting a person to a group of people who are meeting, this was for the person who wants to do something and would like some company.

We’ve probably all been in the situation where despite the enormous number of friends and contacts in our network, we’ve wanted to go and do something but didn’t have anyone to do it with. There can be a sense of being alone in a crowd at these times.

This was a concept for a tech startup I co-founded with one of my best mates, Ren Becker. Project X didn’t get as far as getting a name and brand. We did a bunch of research but decided not to pursue it.

Group chats have probably solved a lot of this need. For example, a couple of years ago I started a Whatsapp group called the Sydney Gig Crew that has grown to over 50 friends – and friends of friends. We’re a bunch of people who love live music. We post gigs we’re going to or are keen to see… and more often than not get a crew together. It’s also become a good place to sell/buy tickets when someone can’t make a gig they’ve bought tickets for.

I explored Project X as part of the Dynamic4 Ventures portfolio.

Smart Locale

Smart Locale logo

Founding Member with Institute for Sustainable Futures UTS, Green Capital, Flow Systems, Pyrmont Ultimo Chamber of Commerce, Echo Entertainment Group & Sydney TAFE. Collective Impact Initiative
2014-2017 (age 38). Sydney, Australia

Smart Locale was a collective impact initiative by Green Capital and the Total Environment Centre. The initial focus was the Ultimo Pyrmont precinct in Sydney. The mission was to “accelerate the transformation of the Ultimo Pyrmont local economy into an internationally recognised showplace for smart, safe, sustainable living by 2020.”

Smart Locale Ultimo Pyrmont provided the backbone organisation and support for a range of projects as long as they were consistent with the vision, follow a collaborative approach, and align with one or more of the six pillars: sustainable buildings, energy, waste, transport, open space, and water.

Smart Locale: Building Smart Sustainable Local Economies

The initiative was guided by a steering committee made up of representatives from some of the participating organisations: Dynamic4, Institute for Sustainable Futures UTS, Green Capital, Flow Systems, Pyrmont Ultimo Chamber of Commerce, Echo Entertainment Group, and Sydney TAFE.

Good Locale was part of the Dynamic4 Ventures portfolio and Dynamic4 designed and built the platform as the digital partner.

We also provided a Dynamic4 Good grant to the value of $25k. As part of the grant, we worked with the Smart Locale team on the strategic design of the value proposition, business model, service blueprint, and brand. I also designed the visual brand.

Sydney Design Thinking (SydDT)

SydDT logo

Co-founder with Kingsley Jones, Lucas Mara, James Cooper & Zoe Gibson. Design Community/Social Enterprise
2015-ongoing (age 39). Sydney, Australia

Sydney Design Thinking (SydDT) is a diverse community of 9,000+ members. We’ve been meeting monthly since 2015 to explore the world of design thinking as a human-centred design approach to innovation and solving complex problems – to help create positive outcomes for people, our planet, and business.

It’s free to join the SydDT community on Meetup.com! Next month on 13 June is our 100th meetup, and we’ll be celebrating our ninth birthday. I’ve only missed five SydDTs in nine years.

We’re one of the top design thinking meetups globally. You can watch some of our meetups on Youtube. Check out the SydDT playlist.

We keep it pretty casual with plenty of time for networking. We’ve covered a very broad range of topics over the years and used a mix of format. Speakers with an engaged Q&A that often turns into a group discussion, fireside chats, panels, workshops, open space and more.

In February 2017 we even co-designed a song with Steve Mulligan leading it, playing guitar, and doing vocals, Jason Davey on drums, and Ben Nicholls on bass. They’d never played together. It was awesome!

The origin story is Kingsley posted the group on Meetup.com and within a day I’d joined as co-founder providing the venue and getting our first meetup organised. James and Lucas then got involved for the first meetup, and Zoe joined not long after.

Kate Linton then officially joined the team in 2018, but had already been involved since 2015 with Thoughtworks being our key sponsor. Kingsley and James left the team in 2019 when both moved interstate. We welcomed Kylie Mageropoulos to the team in 2023.

I reflected on the first part of our journey in 2016 when we reached 2,000 members in 15 months. We’re on the countdown to 10,000 members and I’ll do a deeper dive reflection when we reach that milestone.

SydDT is part of the Dynamic4 Ventures portfolio and supported by Dynamic4 Good grants.

Value Machine

Value Machine logo

Co-founder & CTO with Anthony Quinn. Tech Startup/Social Enterprise
2016-2017 (age 40). Sydney, Australia

Value Machine was a social enterprise startup focused on streamlining philanthropic grantmaking.

We did a lot of research and there was (and is) no shortage of evidence of the problem. There were plenty of animated stories of how painful the current state is – from both grant applicants and grantmakers. We were also able to quantify that in financial terms.

We shared our concept for a solution with a lot of the leaders in the sector, and again there was enthusiastic support. But none of that enthusiasm converted to an organisation that was willing to be the first paying customer or partner.

I’m glad we took a robust sell before build approach.

I still hear how much of a wasteful and painful problem this is. I really wish incentives and priorities were aligned to address it, but this is a complex challenge with entrenched power dynamics. Here’s a version of our pitch deck from 2016.

In 2021, Margaret O’Brien from Young Change Agents – who we’d interviewed for Value Machine a few years earlier and was also a long-term client of Dynamic4 – convened a collective called Reimagining Grants. I joined the convening team with Marg, Julia Keady, and Judit Brown.

We facilitated a few workshops and got great engagement from all perspectives in the grantmaking ecosystem. 110+ people got involved in the initiative. SmartyGrants gave it a write up too, and they’re the dominant player in the space. Marg also produced a whitepaper with key findings. And then it faded away too.

Reimagining Grants and The Problem Company are a couple of ideas/startups I explored with Marg, and they probably could’ve made this list of startups. Together we were founding board members of SECNA and were two of the original people who made the decision that it was time to make it happen in 2019.

Value Machine was part of the Dynamic4 Ventures portfolio and Dynamic4 designed and built the website as the digital partner.

Better Goals

Better Goals logo

Co-founder & CTO with Tymon Kennedy & Andi Smith. Disability Assistive Tech Startup/Social Enterprise
2016-2021 (age 40). Sydney, Australia

Better Goals was a social enterprise focused on helping people with intellectual disability, their families, and supports not miss out on things, build more independence, and achieve their goals.

The very accessible Better Goals app helped people know what they had on, what they needed to do to get ready, how they were getting there, and what they needed to do after. There was a photo and video diary with simple ratings to keep track. They also invited people like their family and support workers into their Better Goals team to share what they’re up to and get help.

Tymon was the original founder and was working as a disability support carer. He was frustrated by the segregation of the people he worked with. He wanted his clients to feel empowered and included – and that gave him the idea for Better Goals.

Tymon was accepted into the first cohort of the Remarkable disability/assistive tech accelerator in 2016 where I was a mentor (and still am). That’s not actually how we met though. Tymon found me and made contact when he was searching for people who had a deep understanding of universal and inclusive design, tech, and was values aligned.

Tymon felt he wasn’t ready for Remarkable and deferred to the second cohort in 2017. I continued working with Tymon with a custom version of our Jetpack program to understand the needs of the users and do the strategic design of the business model and MVP experience.

We designed the brand and then designed and built the clickable prototype for the ING Dreamstarter crowdfunding campaign and video. I provided a Dynamic4 Good grant to subsidise the work to this point, and we ran a successful crowdfunding campaign in late 2016.

We needed to get the MVP live before starting Remarkable in April 2017. I gave another Dynamic4 Good grant and took an equity position to make the numbers work. And Tymon convinced me to officially join as co-founder & CTO. We got our NDIS registration during this time too.

Dynamic4 continued as the digital partner and we did the UX/UI design and build of the MVP as a mobile assistant applying Easy Read principles for people with intellectual disability and their family, carer, and support team. We did ongoing usability testing with plenty of iteration.

Just before starting Remarkable, Andi also joined the team as co-founder & COO. We made so many great friends on Remarkable, including Max and Justine from WheelEasy who I still work with as their virtual CTO/CPO today.

Over time we grew the team with Caroline Vendramin (UX/UI Designer) and Diego Fernández Ruiz (Lead Software Developer) from my Dynamic4 Digital team working part time on Better Goals for equity. Andi left the team when she moved away from Sydney.

We had some active use by our primary audience but decided to invest in building features for disability service providers. The plan was Better Goals could be integrated into their programs and they could assist with onboarding and ongoing use. Key parts of this were focused on being a comms channel and getting program feedback using the visual diary.

Another key thing we focused on was making shift handover easier for support workers who work with multiple participants. If they were invited into the participant’s Better Goals team, they could switch profiles to see key information about their preferences, routines, and what had been happening recently with the handover snapshot.

A core principle for Better Goals was always that the person with intellectual disability was at the centre and controlled who they invited into their team and had access to their information. We took the principle of “nothing about me without me” very seriously, and this drove every design and business decision.

Better Goals Screens

Over the years we raised $105k in grants and crowdfunding. We came close to raising capital a couple of times with one on a profit share deal. The deal was sealed with a handshake and a shot, legal paperwork drawn up… and then we got ghosted. There were plenty of red flags we were ignoring on the deal, and I put this in the category of being very lucky we dodged the bullet.

After five years we weren’t able to get the traction we needed – either with enough daily active use by people with intellectual disability and their immediate teams, or by disability service providers. We made the tough decision it was time to bring it to an end.

We provided a Dynamic4 Good grant to the value of $20k. Better Goals was part of the Dynamic4 Ventures portfolio and Dynamic4 designed and built the platform and app as the digital partner.

Hero Investor

Hero logo

Co-founder & CTO with Justin Medcalf & Anthony Quinn. Purpose-Driven Fintech Startup
2016-2017 (age 40). Sydney, Australia

Hero was a purpose-driven fintech startup focused on helping self-directed investors find and access meaningful investments in companies of the future.

The problem we identified is that self-directed investors want to back the next wave of progressive companies but lack the expertise, find them difficult to access, and struggle to find meaning in their investments – beyond pure financial return.

Our solution concept was a platform and community that would match investments based on the values of the investor with a mix of education and (robo) advice.

Justin got Quinny and I involved because we’d been collaborating on some other ideas, and we had relevant skills and experience – though there was probably too much of an overlap. A VC Justin knew indicated they’d be interested in something along these lines and we kept her informed while we did the initial research and solution concept. We then pitched it to the partners and received an offer.

The offer wasn’t founder friendly but I actually thought it was fair given how early the idea was. The VC wanted 75% (a controlling share) and would impose restrictions on use of funds which didn’t work for my co-founders. We also had concerns about the mission-lock being removed. We declined the offer and it was game over.

Justin and I would try again a couple of years later with a related idea called Climate Solutions Group.

I explored Hero as part of the Dynamic4 Ventures portfolio.

Ripple

Ripple logo

Co-founder & CTO with Tom Dawkins. Tech Startup/Social Enterprise
2017-2019 (age 41). Sydney, Australia

Ripple was a social enterprise startup focused on helping people bring their community together to donate to the causes they care about.

This was based on the giving circle model where there’s complete transparency and members of the group choose their impact focus, donation amount, and frequency. The members of a circle might be friends and family, a workplace, school, book club, meetup, or community organisation.

Ripple platform screenshot

The backstory to this one was that Tom Dawkins from StartSomeGood (another B Corp) was a co-founder of another giving circle social enterprise and they engaged Dynamic4 as their digital partner. Dynamic4 funded most of this with a Dynamic4 Good grant. We got the platform live and some circles started activating.

Then things went sideways with the co-founders, with one ghosting the other two. She was the one with control of the bank account and after several promises to pay long-overdue invoices to Dynamic4, ghosted me too. Payment didn’t come and IP ownership didn’t transfer because of it.

I won’t name the other startup or the rogue founder, but you tend to think people (especially very high profile people) in the NFP space would behave with at least a minimum level of ethics. This was the worst behaviour I’ve ever directly experienced in startups or by a client.

Ripple was an attempt to salvage the investment, and Tom was keen to make it happen. Bryony Green was the other co-founder and is awesome. She stayed involved as an adviser.

Pretty quickly Tom and I knew we didn’t have the capacity to run it and do the community building needed to get the giving circles up and running. We made a few attempts to find someone to come on as co-founder & CEO, but didn’t have any luck.

The original business model had never been tested. As much as I wanted it to work, I was keeping an eye on sunk cost fallacy and wasn’t going to invest any more into the platform before there was evidence of paid demand – or at least active use.

By this point in my startup life, I was really over trying to fix business model problems with product features. I’d been through that loop too many times and knew it doesn’t work.

After it being in zombie mode for a while, we finally called time and drew a line under it.

Ripple was part of the Dynamic4 Ventures portfolio, mostly funded by Dynamic4 Good grants (an embarrassingly large number), and Dynamic4 designed and built the platform as the digital partner.

Climate Solutions Group

Climate Solutions Group logo

Co-founder & CTO with Justin Medcalf & Blair Palese. Purpose-Driven Fintech Startup
2019-2020 (age 43). Sydney, Australia

Climate Solutions Group was a purpose-driven fintech startup focused on democratising impact investing in climate solutions by accelerating project finance – connecting investors to the right projects and removing structural funding barriers for small scale projects.

Our solution concept was an investment platform that would enable everyone to back the climate solutions we need for a safe climate future. Bringing climate projects to everyday people with a low minimum investment of $50.

This would require a blend of movement making, education, legal and finance structuring, and tech. We aimed to bring together funding from wholesale investors and retail investors (equity crowdfunding) to provide project originators with a reliable and efficient source of capital at a competitive price – and that was backed by the community.

This is a very complex set of things to bring together, especially without capital. We didn’t manage to get the non-tech bootstrapped versions of the deal flow to happen, and decided the only path forward was by raising capital. Then the pandemic happened and it was truly game over.

I explored Climate Solutions Group as part of the Dynamic4 Ventures portfolio.

Social Enterprise Council of NSW & ACT (SECNA)

SECNA logo

Founding board member with Cindy Mitchell, Kylie Flament, Laura O’Reilly, Lee Cooper, Margaret O’Brien, Mikey Leung, Tess Ariotti, Tom Dawkins, Jay Boolkin & Laura Reed. Social Enterprise Peak Body
2019-ongoing (age 43). Sydney, Australia

I was a founding board member of SECNA from 2019 and left the board when I reached my max term in May 2023. I was also the treasurer for most of this time. I shared a detailed version of the backstory and my reflections in Reflecting on 4 Years as a Founding Board Member of SECNA.

It was a privilege to work with so many awesome people during those four years – making the decision that it was time, getting it off the ground during the pandemic, and then building and sustaining the momentum. I’m no longer on the board but Dynamic4 is still an industry member and I’m an active volunteer.

If you’re in or around social enterprise in NSW or ACT… get involved!

Solve Problems That Matter Book

Author & Designer. Physical & Digital Social Enterprise Product
2021-ongoing (age 45). Sydney, Australia

Solve Problems That Matter PDF Cover

I approached writing Solve Problems That Matter as a startup. I designed it as a product of Dynamic4 rather than a traditional book. As I mentioned, this is an extension of our Jetpack program in book format… and traces its roots back to our Design for Meaning/Make Business Good collective.

It’s a playbook (82,000 words and 350 pages) supported by free worksheets, resources, and the social enterprise healthcheck. It’s structured as a 90-day program to help you take a human-centred design approach to design, build, and launch your idea. Ideas that customers love, makes money, and does great things for people and our planet… all while increasing wellbeing.

It also hit the Amazon #1 best seller in both of my categories: “Entrepreneurship” and “Nonprofit Organisations and Charities”.

Ben Pecotich smiling, wearing a black tshirt, and holding his book Solve Problems That Matter

The book perfectly complements the learning programs I design and deliver and the coaching work I do. I love seeing it in the wild and the photos I receive from readers showing their very well-used and marked up books. That’s exactly why I wrote it. 1,000+ copies in 26 countries and 71 cities.

Even though I’ve been doing this work for over three decades, I’m learning every day. And I always will be. Very few things are static. Contexts change, trends and patterns emerge, new technologies come to market. Sometimes this happens slowly, other times suddenly and dramatically. The covid pandemic being a very real example.

Continual iteration is how I work and experience the world… this means I’m always learning, and my thinking evolves. This might be from a conversation, things I read, trends I observe, experiments I run, insights from the people and organisations I work with.

My initial thinking was to self-publish a digital-only version on Amazon, and possibly do a small print run depending on demand. From my early research, a key message I heard was most of my target readers buy this kind of book in a print format – and many buy both print and digital… but a print version was a clear expectation.

What did that mean for my book? A print book is a snapshot at a point in time, but I needed to create space for refinements – without the need to write a new book. The key way I approached it is to make some resources freely available. This includes downloadable worksheets as well as links to websites, articles, books, and events.

The other thing I’ve done is refine the book based on feedback. Because I’m an indie author with publishing control, I’ve been able to do this with both the digital formats and print. When you buy the book in the digital formats, you get the refined editions for free. The version number and date are on the copyright page of all formats. Check out the release notes.

I shared my story as I progressed, the many lessons I learnt, and opportunities to get involved. This started with a blog post to test interest and demand for the book format of our Jetpack program – and to test the key questions and content I planned to cover. It’s a journey in progress… you can follow the story here.

Interaction Week 2024 (IxD24)

IxD24 logo

Education Summit Co-chair & IxD24 Organiser with Vera Chan, Susan Wolfe, Martin Tomitsch, Kevin Chan, Kevin Wilkins, Mary Nolan & Vinita Israni. Purpose-Driven Design Community
2022-2023 (age 46). Sydney, Australia

I was part of the small volunteer team who put together the winning bid for Sydney to be the host city, and the team to organise Interaction Week 2024. I was also co-chair of the Education Summit with Martin Tomitsch. IxD24 was planned for 25 February-1 March 2024 in Sydney with the theme Revisit. Reframe. Regenerate.

I’d been involved with IxDA Sydney since the early days as a member of the community, a mentor on the mentoring program from 2013, and helped organise the meetup for a few years as one of the local leaders.

A community focussed on building capability to take a human-centred approach to the design of digital solutions, products, services, environments, and systems – with a strong focus on behaviour and designing for great experiences.

Interaction Design Association is a member-supported network dedicated to interaction design and brings together a global community of 120,000+ people and 200+ local groups. Interaction Week was the annual global conference.

Sadly IxD24 was cancelled in October 2023 due to IxDA global’s financial situation – turns out they were insolvent and deeply in debt. The legal entity is being dissolved.

As a local volunteer team, we invested a huge amount of time on the bid, curating the program with so many great speakers, and designing the experience we wanted our global audience to have during the week. The team grew well beyond the bid team I listed above and I’m proud of the work we did.

IxD24

I learnt a huge lesson from this on doing enough due diligence – even if it is a global not-for-profit. As a local team, we had no visibility of IxDA global’s finances and all ticket sale payments went to them directly. When we found out – mostly accidentally – that they weren’t solvent and we’d have to cancel the conference, I was gutted and felt extremely betrayed.

It was a shocking governance failure at the global level. But it was also my failure to do the due diligence I should’ve. I won’t list some of the things I found when I went digging after the fact because it doesn’t seem to be public and there was talk of a legal process, but after more than six months, there seems to have been no accountability.

The thing I take from it though is we have an awesome local design community, we collaborated really well, and are still great friends.

What I’ve Learnt

As I said… my past 30 years of startups have been full of learning, failing, iterating, and adapting. And still are.

Here are some reflections on key things I’ve learnt.

Co-founders

Firstly, a massive thanks to the co-founders I’ve been on this adventure with. I’m grateful I’ve had the chance to work with and learn from so many awesome people… in both my startup and corporate lives.

A lot of the ideas I’ve worked on weren’t mine, at least initially. I’ve been lucky to get invited to come and play, including by people I’d never met before.

Co-founder relationships are tricky. It would be ideal if everyone working on the idea was equally committed, but that’s rarely the case. People’s situations and energy are different, change over time, and are pretty much never equal. If you have this expectation, you’re probably going to be disappointed.

The high priority work to be done, workload, and the skills required vary a lot – especially in the early stages. It’s nice to have at least one other person in the mix with complementary skills to help balance the workload.

Sales and marketing – including storytelling for persuasion – are my weakest areas in business. I’ve almost always partnered with someone who is stronger in these areas than I am.

A lot gets said about needing a co-founder but the data is mixed at best and there isn’t clear evidence that startups with two or three founders are more successful than solo founders. Like any relationship, it’s usually better not to be in one, than to be in an unhealthy one.

For The Founder’s Dilemmas, Noam Wasserman from the Harvard Business School studied 10,000 founders, and his research showed that 65% of startups fail because of co-founder conflict. I’m glad that’s never been the reason why a startup I’ve co-founded has failed.

Another study looked at over 500 startups that raised more than $10 million in funding and found that 46% were founded by solo founders, 32% had two founders, and only 22% had three or more founders. I think it’s better to get started and build a team.

Over the past decade, I’ve invested the time to deep dive and align expectations with my co-founders before jumping in. It also tends to be something I cover very early when I’m coaching founders. I included the questions I use in my book Solve Problems That Matter (p316).

This conversation can be confronting to think about and hard to talk about, but the objective is to get things in the open, so you can address them before things go wrong. You might not agree on some of the points, but it’s better to find that out early and reach an agreed position, rather than avoiding them. Hard conversations don’t get easier when they’re delayed.

I’m also a fan of using Slicing Pie to transparently track and financially reward based on actual contribution rather than potential. That’s a rabbit hole I’ll sidestep for now… and a thread for another time.

In summary… I’m happy to go solo. But I also don’t need to be the one with the original idea. I’ll jump in wholeheartedly if it’s something I really care about, I can see the potential, it’s with people I want to work with, and I feel I’ve got plenty of value to add. To me, ideas are disposable. It’s always about the ability to deliver… and a heavy dose of luck.

Wellbeing & Personal Sustainability

Startups, if they go well, are a long game. A very long game.

Often in the excitement and sometimes because of the sense of urgency, I’ve dived in and overinvested time and money in ideas without doing enough due diligence. I’ve also let the startup… or in my case startups… become all-consuming.

I’ve been on this intense but mostly fun journey for many years. For a long time, it consumed every waking moment – and many of my sleeping moments too. Especially with the social enterprise lens. It’s been how I pay the bills, my social life, and my hobby. My default state has been to drift into thought about work… especially strategy. I still practice my happiness habits and work on my sustainable rhythm.

Our personal sustainability and wellbeing are the most important things. If we don’t have that, we don’t get to keep playing the game. This is often the first thing I coach people on. The approach I take is to help founders build habits that integrate wellbeing and happiness habits into their workflow.

Our physical, mental, and emotional health are completely linked. The health of our mind affects our body, and the health of our body affects our mind. We need to look after both – like they’re one. Because they are.

Economic or financial wellbeing is also an important part of our personal sustainability. Our ability to meet our basic needs and feel secure. It’s common to talk about the startup’s runway – how long before it runs out of money. It’s less common to hear about personal runway.

It usually takes longer than we plan to break even on a monthly basis – the point where we have more money coming in every month than we’re paying out. Most financial models I see also don’t include the founders paying themselves – and even then, the numbers often don’t stack up.

I recommend putting together Your Personal Wellbeing Plan. In Solve Problems That Matter, I go into a lot more detail on all of that – with a focus on building habits that integrate wellbeing and happiness habits into your workflow.

Sales & Revenue

I can keep this one brief. The go-to-market strategy, marketing, and sales are everything. It pains me to say it, but it doesn’t matter how good your product is if you can’t sell it and people don’t find out about it.

It’s not fair. Marketing beats quality, at least in the short-term… and if you can’t play the game, you’re probably not around long enough to win.

Over the years I’ve got better at having the discipline to take a sell before build approach. If we can’t sell the value prop and the promise, having a quality product isn’t going to make a difference. It just means we get stuck with a high quality product we can’t even get people to use for free.

Two key lessons I’ve learnt on this…

For most solutions, the primary barrier is getting people to pay with their time and attention – far more than the price – and a lot earlier than the price becomes a factor.

You can’t solve business model issues with product features. This is the trap I’ve fallen into far too many times. Adding features and polishing the product, when the real issue is the value prop, or because the problem it just not a high enough priority for the target customer to do something about right now.

Luck, Risk, Failure & Learning

I’ve been really lucky to have had the freedom to explore these startup ideas over the past 30 years.

But what is luck? It’s an interesting area of research and Richard Wiseman’s findings are “it’s something we create with our thoughts and behaviour”. The core of this is our mindset and how we view risk and failure.

Mindset and happiness are things we can all develop to be lucky and successful but I also recognise the role of random chance in me being born into relative systemic privilege.

As Scott Barry Kaufman said in his article The Role of Luck in Life Success Is Far Greater Than We Realized “…the data suggests that we miss out on a really important piece of the success picture if we only focus on personal characteristics in attempting to understand the determinants of success.” Worth a read for some fascinating research, simulations, and findings.

Part luck and part judgement – like so many things – is timing. Bill Gross talks about this in his 2015 TED talk. He studied 200 companies and looked at the critical elements of the idea, team, business model, funding, and timing. He was looking for the factors that explained why the companies had succeeded or failed. He found that timing was the number one thing and accounted for 42% of the difference between success and failure.

Research also shows that saying yes and being open to possibilities increases our luck. I wrote about that a bit more in my Open & Curious post a few years ago. To get lucky you need to show up and be in the game.

One of the principles of action learning I love is that the people who choose to take responsibility in a challenging situation have the best chance of positively impacting and resolving the challenge. When you say yes and get involved, you give yourself the chance to get lucky. If you sit on the sidelines, you don’t.

I grew up without much in low socioeconomic areas in both Sydney and Wellington. In a lot of ways this was good training for startup life. You’re creative and innovate out of necessity. You persevere and keep striving because the alternative is too grim to face. You build confidence that you can navigate adversity. You learn to do a lot with a little. All key ingredients you need in the early stages of a bootstrapped startup.

No one in my family has ever gone to university, and it wasn’t an option for me. I’ve always been about lifelong learning though. I guess startups became my ongoing real-life MBA.

Despite not having a degree or formal education, I get to share my experience with university students – at both an undergrad and masters level – with the project-based/work integrated learning programs I’m involved in at multiple universities… and with my book Solve Problems That Matter.

I’ve never made life changing money from any of my startups (yet). But by working on startups for 30 years, I’ve learnt more in applied ways than I could in any other way. I’ve designed the life and lifestyle I want with plenty of freedom to explore my endless curiosity.

For that, I’m lucky and forever grateful.