50 lessons from 50 successful founders, investors and industry experts (Part 1/5)

*Note: I got through the first 10 lessons and was at 3,000 words…Instead of writing a 15,000 word blog, I have decided to split the post into a 5 part series. This is Part 1 of the 50 lessons from 50 successful founders post
**Update: Part 2 is available

Roughly 10 months ago, I launched The Startup Playbook Podcast with the aim of helping better connect, provide education and become the go-to resource for anyone in the startup ecosystem.

I wanted to launch the podcast because of 3 main reasons:

  1. Instead of learning theories, I wanted to provide a reference point for founders to learn from people who had “been there and done it” who could talk through their lessons and experiences
  2. Creating greater perspective and visibility from different sides of the table (i.e. what does an investor actually look for)
  3. I was blown away with some of the conversations I was having and selfishly wanted to create a resource where I could keep the context of what was discussed and absorb the information in a deeper way (plus I hate taking/ rereading notes).

It took me 3 weeks from deciding to do a podcast, figuring out what equipment to use, how to edit, reaching out to people, recording and launching the podcast. 3 weeks later, the podcast hit №3 on iTunes for it’s category.

A large part of the early success was a combination of luck, timing and strategy that I used to get the widest distribution possible from shoutouts on large mailing lists to directly emailing 107 people that I had met for coffee over the last 3 months to help them with their business. I wrote an in depth piece about how I did it here.

Fast forward 10 months and I have just launched the 50th episode of the weekly show!

I have been extremely fortunate to have some truly incredible guests on the show, each with their own perspective and story on why they did what they did and the reasoning/ judgements behind particular decisions. From each guest I learnt a unique insight or piece of wisdom to apply to my business and my life.

To celebrate the 50th episode milestone, I wanted to take a look back at each episode/ guest and share the unique lesson I took out of it.

Tim Mundy — Founder & Director of Digital Affair

Lesson 1 — Tim Mundy (Digital Affair) on Turning a network into a business.

Tim Mundy is the founder and Director of Digital Affair, an HR branding agency that had an astonishing amount of success since launching less than 2 years ago (and has grown even faster as discussed in Episode 50).

On the day of their launch, they had already established a partnership with LinkedIn and when we spoke in the first episode, they had already amassed a client base of some of the biggest companies in Australia including Motorola, Coles, Lion and Bunnings Warehouse.

We covered a lot in the interview with Tim and one of the common themes that comes out from the interview (and if you ever meet him in person) is how much Tim focuses on giving first.

Tim did this numerous times through hosting roundtables and lunches while he worked within the corporate environment to bring people together and create a community around other professionals in the space. He also spent several years teaching professionals how to get the most out of LinkedIn.

By doing this he had a ready made audience to reach out to when he decided to launch Digital Affair and also through some of the work he did to train people in the best practices on the platform, Digital Affair was able to launch with a partnership with LinkedIn on the first day of business.

You can listen to the full interview with Tim where we discuss how to get clients, foster partnerships and build teams here.

Shelli Trung — Angel Investor

Lesson 2 — Shelli Trung (Angel Investor) on building relationships with investors

Shelli Trung has had an interesting career to date. She started as a successful real estate investor before starting her own startup which she then exited. She is now an active angel investor and was named as one of the “Top 100 investors to follow on Twitter”

One of the common themes to come up from the chat with Shelli was the need to be extremely targeted with the investors you are reaching and the need to build relationships with them vs focusing on a transaction.

Shelli mentioned that by focusing on investors that had an interest in her sector, they were able to quickly identify (and help fill) some of the gaps in her business as well as understanding her business a lot better which was critical in not just getting their money, but also their ability to help.

One of the key aspects of Shelli’s background is that having been a founder and investor, she has had experience from both sides of the table and one of the important factors she identified was the need to build real relationships with investors vs focusing purely on the transaction of getting their cash.

One of the common themes that came out of several other podcast episodes was that early stage investors often invest in people not ideas and so a large proportion of investment decisions for investors at the early stage is based on the credibility of the founders and the relationships that they have built with them.

Hear from Shelli on how to approach investors and get them interested in our full interview here.

Justin Dry — Co-Founder & Co-CEO of Vinomofo

Lesson 3 — Justin Dry (Vinomofo) on the need for passion

One of the most incredible stories shared on the podcast was the “lean years” that Justin Dry and his co-founder Andre Eikmeier went through. The lean years were the 4 pivots over 4 years that Justin and Andre navigated whilst trying to find the right business model and idea. This was heightened by the fact they are brothers-in-law which added further pressure not just for the founders but their family.

Justin and Andre finally found success with their 4th model with Vinomofo, the group buying, daily deal site for premium wine. Vinomofo recently raised $25 million in funding from Blue Sky Venture Capital and is recognised as one of the biggest success stories in the Australian startup scene.

One of the questions I asked Justin during the interview was if he wished they had jumped straight to the Vinomofo model (and if the company would have still been as successful) and Justin’s response was there would be no way the company would have been anywhere close to the success of their new business.

This was because the community they had built (who became the early adopters of the platform), the relationships they developed in the industry (which allowed them to get their first set of deals/ discounts that were unmatched by their competitors) and the lessons learnt over the first 4 years were a large part of the reason why they were able to build on and create a successful business of the back of the new model.

You can hear the incredible story behind Vinomofo and Justin’s advice on building communities, when to pivot and choosing between multiple options on the table in the full interview here.

Alex McBride — Founder & CEO of The Fifth

Lesson 4 — Alex McBride (The Fifth) on turning your weaknesses into strengths

Alex McBride is the founder of The Fifth Watches, a watch & lifestyle brand that was built around his curiosity with design. Alex and his team spent several months building an audience on Instagram using their “The Fifth View” as a unique concept to build their visual brand around.

They finally launched their first set of products and then the unthinkable happened, they sold out of the products on the first day of business (Don’t worry, I was very jealous hearing about this as well!).

As a small brand with limited budgets and small production runs, it was an issue because they felt that they wouldn’t be able to keep up with demand and felt that they would leave a really negative experience for their audience.

So instead of doing what every other e-commerce brand did which is to dramatically increase production (huge risk for a new business) or just have sold out banners everywhere (poor experience for customers who want your product), they came up with a unique business model*, where they would sell their products for only 5 days on the 5th of each month. This allowed them to streamline their internal processes, guaranteed product if you ordered within the 5 day period and helped them stand out as a brand and build hype around their product, giving them an edge in the market.

When I interviewed Alex, they had just celebrated 18 months since the business had launched, with the brand dominating social media, with over 500,000 followers across their social media channels.

*Disclaimer: The Fifth recently did their first $1M sales day and have since opened their model from the initial restrictions. You can read all about it here.

You can hear the full interview with Alex where we spoke about building a business from a blog, turning weaknesses into strengths and how to grow a social media following here.

Paul Napthali — Co-Founder & Managing Partner at Rampersand VC

Lesson 5— Paul Napthali (Rampersand VC) on the need for optimism and paranoia

paul naphtali is the Co-Founder and Managing Partner at Rampersand Venture Capital.

Prior to starting Rampersand, Paul was involved in several successful startups with large acquisitions. He played roles within the PR and Marketing teams at startups such as Snaptu (acquired by Facebook) and TokBox (acquired by Telefonica).

Paul then moved back to Melbourne to launch Rampersand Venture Capital a $50 Million fund, to invest in early stage technology startups.

We covered a lot of things in the podcast interview such as when and how to contact VC’s, the common ingredient that he sees in successful founders, the Rampersand investment process and what the biggest turnoffs are for investors.

One of the areas where we dived into was the point Paul mentioned about the best founders balancing being extremely optimistic with being extremely paranoid — something he has since written about in great detail here.

Paul mentioned that the best founders have a keen sense and understanding of the challenges and barriers ahead of them but balance this with the optimistic outlook that despite the challenges and the numbers, they have a belief that they are the outlier and can make it work.

The full interview with Paul is available here.

James Nguyen & Matt Snowden — Founders of M5859 Apps

Lesson 6 & 7 — Matt Snowden & James Nguyen (M5859 Apps) on creating opportunities & short term “loss” for long term wins

My interview with Matt and James was so packed with information we had to split it into 2 episodes!

Through M5859 Apps, Matt and James have developed a strong track record of building successful and scaleable apps. Their app “walking with dinosaurs” was named as the app of the year for 2012, went number 1 in 22 countries and had over 500,000 downloads.

Over the entire interview we covered everything from using addictive loops for in built virality in products to how to use connectors to partner with companies like Apple and A-List celebrities like Taylor Swift.

My two key takeways from the interview were:

#1 You can put yourself in an position to take advantage of opportunities. Both Matt and James spoke about how they used things like volunteering, running workshops and offering value to people as ways to build credibility and trust to not just decide who to work with, but helped them land clients for them to grow their business.

#2 One thing that not a lot of people consider is taking on perceived short term “losses” for a much bigger upside. At a time when most apps on the app store were selling between $12-$16, Matt did something that was unheard of at the time, which was to offer free downloads of the app. He then created a strategy to get the widest possible distribution with the app then hitting #1 on the App store in 22 countries.

In other words, Matt was willing to give up the short term revenue he would accrue from downloads to build an audience who he would then be able to use a distribution strategy (and have credibility) for future products he wanted to launch.

You can listen to Part 1 where we discuss finding the right cofounders, giving away value and contacting Taylor Swift here and Part 2 where we talk about creating virality, getting 500,000 downloads and building marketplaces here.

James Cattermole — Angel Investor & Founder of Hexigo

Lesson 8 — James Cattermole (Hexigo) on the process behind enterprise sales

James Cattermole is a serial enterprise software entrepreneur who has 2 successful exits under his belt and is now on to his 3rd business as well as being an active Angel investor in early stage enterprise startups.

His first business, VNH Systems was a DVD rental software which sold to Blockbuster in 2007, immediately after selling his first business, he founded JadeLynx which was then acquired in 2013. He is now the Co-founder and CEO of Hexigo, an enterprise prioritization system, that is helping large organisations better manage and utilise their emails.

During the interview, James shared a complete playbook in how to launch and grow enterprise software companies, covering topics including: How to transition from corporate life to startups, how to find and spot good ideas, how to action feedback into pivots, the one question you need to be able to answer clients, the challenges of expanding overseas, what startups should look for in investors and the one caveat where giving your software away for free makes sense.

My main takeaway however was the approach that James recommended in selling into enterprise clients, which is something that a lot of new (and first time) SaaS startup founders struggle with.

James outlined his process in detail on the podcast but his overall process was the following:

  1. Look inside your own networks. With the reach of LinkedIn now it’s easy to research and see who to reach within specific organisations. Chances are that you also have a 2nd or 3rd degree of connection who may be able to provide an intro to that specific person or to someone within the organisation (warm intros work much better than cold outreach)
  2. Buy lots of coffee. If you are able to demonstrate credibility or are able to leverage a warm introduction, use that to offer a catchup over coffee (most people will say yes to a free cup of coffee/ tea!). Use these coffee chats to get an understanding of the business pain points, the sales process internally and the decision makers who you will need to get through to close the sale — chances are you will need to do this over multiple meetings to foster the relationship
  3. Repeat — use the introduction to move higher up and closer to the key decision makers and shout them a coffee! B2B sales are all about relationships and the bigger the organisation, the more relationships you will need to build (depending on your access point) to close the deal. This is why SaaS products have long sales cycles and for a startup to succeed in the space, it needs to have a long enough runway to capitalise on the relationships being built.

Listen to the full masterclass on B2B sales with James Cattermole here.

Angus McCulloch — Head of Growth at The Fifth

Lesson 9 — Angus McCulloch (The Fifth) on understanding the role of social media in your sales process

Angus is the head of growth at The Fifth watches, which we went over in episode 4.

Angus is a marketing and growth expert, who has a particular expertise in building and growing large followings on Instagram for businesses. When I spoke with him in August 2016, he had amassed a following of over 1.6M across 5 different Instagram accounts.

His experience in building large followings has allowed him to help companies such as The Fifth Watches succeed as a business based primarily of their Instagram strategy.

In the episode, we dive deep into Instagram and took a look at particular strategies that can help businesses grow through the platform. In the interview, Alex gave his insights into the Instagram Algorithm, How to use engagement spikes to get your account trending, how to use the psychology of Instagram users to decide what posts to put up and why you should upload multiple posts at once.

We dove deep into some of the hacks and strategies to grow your Instagram account which is best described by Angus himself, but my main takeaway from the interview was in understanding the role that social media plays in the buying decision of consumers.

From a marketing perspective, it’s important to understand what the context is of the relationship between the consumer and the brand at any given point of the funnel, what role each platform plays in the consideration of the brand and what are the additional pieces of information or relationship building activities that need to occur for the consumer to convert from initial exposure of the brand to converting into a paid user.

This is something that I am extremely passionate about as it is one of the areas that my company, Playbook Media, specialises in. The process is different for each business and the cycles vary from a day to over 6 months depending on the product/ service, market and industry, I’ll go into this in further detail in another blog post, but on a higher level the process is:

  • Exposure: Someone finds/ comes across your business
  • Consideration: Does the value of the brand/ business align with the customer interests?
  • Credibility building: Is the value and alignment of interests consistent? As a consumer, do I believe the in the credibility of the business?
  • Conversion: Becoming a (paid) user of the business
  • Loyalty: Once they become a paid user, how long do they stick around for and how many future purchases do they make (i.e. what is the Lifetime Value of this customer)
  • Advocate: Do they believe enough in the product or business to refer other people in their network

You can listen to the full Instagram Masterclass with Angus here.

Sujan Patel — Author (100 Days of Growth) and Founder (Narrow.io, WebProfits & Contentmarketer.io)

Lesson 10 — Sujan Patel (Writer, Author, Entrepreneur) on how to get featured by Forbes, Inc

Creating content can be one of the most valuable (and time consuming) activities that a startup founder can do and Sujan Patel has got the process nailed down to a tee.

When I spoke with Sujan for the podcast, not only was he running 3 different businesses at once, but he was regularly contributing to Forbes, Inc, Entrepreneur Magazine & The Wall Street Journal and had written a book titled 100 Days of Growth (you can get a free copy of his book using this link) which had sold over 30,000 copies in the last year alone.

In the podcast interview we broke down his process for creating daily long form content, how to create shareable content and how to distribute your content as wide as possible.

One of the things I was keen to learn from Sujan was how he got to a stage where he is asked/ accepted for contributions to such large and well known publications. Sujan was kind enough to share his process which he prefaced with understanding that it takes time and there is no quick solution.

Sujan’s 5 steps was:

1. Start with your own blog: Start getting into the habit of writing consistently. Find your own voice and structure and build up an understanding of the writing style, content and topics that seem to resonate with your audience

2. Once you are setup with your own blog, start doing guest posts for other companies/ startups or industry publications. These types of organisations are always looking for new content. Start picking up some wins for these blogs (100 odd shares)

3. Once you have had some success with some of the smaller players, start approaching higher calibre sites such as the top 3 publications for your industry such as the leading organisation, institutes or peak bodies.

4. Once you have built your credibility within the industry, start approaching some of the mid-tier publications like Business Insider and Huffington Post that may be relatively easier to approach.

5. Finally you are ready to start approaching the larger publications. As you would have noticed, each stage helps build additional credibility, your writing skills and a portfolio of work that you can then showcase to the next tier of publications. This means that instead of approaching people cold, you have a body of work that you can present to ensure the best chances of being accepted for contributing articles.

You can listen to the full interview with Sujan here.

If you enjoyed this…

Part 2 is now published and available here. Follow me on Medium, Twitter or LinkedIn to be notified when the rest of the series other future blog posts are published. In the meantime, checkout The Startup Playbook Podcast on iTunes, Soundcloud or Stitcher or head to startupplaybook.co for the full interviews and curated tools and resources for startup founders

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