Ryan Windsor: Female Entrepreneurs 'Very Receptive, Proactive and Determined'
by Mark Hogan, 05th June 2015
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"Windsor Properties invests, refurbishes, lets and manages modern properties to hardworking families with hassle free maintenance guaranteed."

Hi Ryan and welcome to our inspiring startup talks with entrepreneurs! Firstly, tell us a what you love/hate about being an entrepreneur. 

I love all aspects of being an entrepreneur and entrepreneurship itself. I get really excited about the journey from the initial idea, testing and proving the concept and then building and scaling a company to become sustainable and profitable. The possibilities to create and start something new are a real passion of mine.

I guess this is why I also lecture in Business Enterprise & Entrepreneurship as well as mentor at Cambridge University’s Judge Business School. Watching these students transform their ideas into real, tangible business fills me with pride and energises me to continue to do more to help these budding entrepreneurs, especially when they are social innovators and their businesses have a real, genuine social impact amongst its stakeholders.

Through my involvement with the charity sector (where I am a Director at Keystone Development Trust), I’ve also been lucky enough to get involved with international organisations working with young people, NGOs and businesses on projects and forums encouraging scientific collaboration, entrepreneurship and cultural awareness. This is something I’m hoping to continue as the opportunities that arise from such events are changing the mindsets and outlook of the participants to start considering entrepreneurship more, it’s really inspiring stuff!

I can’t say I really hate anything about being an entrepreneur. The long hours and traveling does grind on me at times but most of the time I’m completely consumed by what I’m working on that I hardly notice and when you are working with great people who  share your vision it really does help keep you engaged.

When mentoring founders, what are the most common mistakes you come across?

I don’t like the word “mistake”. It focuses on the negative impacts, but mistakes can be particularly helpful to founders in the early stages of their venture. “Fail fast and fail often” is a saying being used a lot!

Although the work I do with founders tries to mitigate failure as much as possible, small mistakes can be very valuable, especially when testing new concepts and trying to develop your customer strategy. If you can learn from them and pivot your value proposition, you'll be that much closer to the magic three words: “Sustainable; Repeat; Business.” (The transition from Startup to a company!)

I’ve been lucky enough to work with and mentor founders and budding entrepreneurs from a range of industries. These have included property, technology, education & training, charities and marketing; all with varied backgrounds. Some founders have years of experience in the sector while some have none. Some are creating new products or services, some are just improving them. Personally, I love the challenge and diversity and being a part of the journey from start to finish.

The “mistakes” I come across most are to do with balance: founders often focus on one aspect of the business too much and either don’t consider the others or just simply forget about them.

An example I can share is a recent one. I have been working with a tech entrepreneur who is a great coder and has a huge amount of determination. He had all the facts and figures for the business and knew exactly what he need to do to get to the next stage of development. He asked me to look over everything before he began pitching to investors. Immediately, I saw his own financial situation was not accounted for! Without factoring this in, there was no way the venture (with its current projections) could have sustained him and his family.

Other “mistakes” I have come across are to do with the actual pitch itself. The founders tend to focus a lot of time on the idea and not enough on the business, implementation and ultimately how/when the investor will get their money back - the number one thing on the investor's mind!

In regards to the person I try and focus on their skills, values, passion and goals in life. The entrepreneurial journey is not an easy one and getting that extra bit of advice and guidance can make a big difference.

What is the best advice you can give to startups?

I believe that startups should be fuelled by passion and innovate a customer-centric solution to a problem that is sustainable. To help aid in the startup's success, I’d also suggest that founders think long and hard on whom they get to join the company especially in the early days as this can be make or break. If you haven’t done so already, read Good to Great by Jim Collins and study his Hedge Hog Principles.

Do you notice more female entrepreneurs crossing your path?

This is a really interesting question. At first, most of the people I worked with were male but I think more and more females have had the chance to discover the opportunities entrepreneurship can offer them and that they can be as successful. Currently 75% or more of all the entrepreneurs I mentor are women, and to be honest, they seem to be very receptive, proactive and determined to turn their ideas into reality. One striking difference I have seen in the difference in female entrepreneurs' work is their ability to network, ask questions and learn from more experienced business people. Which I believe is a key skill to be successful!

You managed to keep a successful academic life while you started up a business. What advice can you give to entrepreneurs in a similar situation?

I can’t say it was easy as they are two completely different kinds of pressures but both were extremely enjoyable. I used my courses (a BA Hons in Business Management at UCS and a Postgrad in Entrepreneurship at Cambridge University Judge Business School) and what I was learning from them as an opportunity to explore and to recognise business and investment opportunities. An entrepreneur should always be learning!

I never really saw a difference; they were one in the same. I’m always thinking about business and investments because it's who I am, so whatever else I’m doing I’m always going to be thinking about the business elements and opportunities for that situation anyway.

If I was going to give any advice I would say be organised, make sure you plan for the worst and surround yourself with likeminded people. It’s hard enough trying to set up a business but if you have negative people criticising you and your ideas all the time it can really take its toll. Instead seek guidance and constructive criticism from people who are in the same boat or who have already been there!

What is the best way for startups to get their name "out there"?

For any business, raising awareness of what it's doing is important. This is even truer for startups who may not have the cash to splash on fancy marketing campaigns.

I tell everyone that I work with that they should think of themselves as an extension of their business - a bit like Sir Richard Branson. Branson runs Virgin and he is Virgin; when you think of one, you think of the other.

To help achieve this, you should be creating a positive image of what you want to portray for you and your company. Having an online presence helps. Communicating clearly with your audience (through blog or video posts for example) can create a following and buzz. Enhancing your relationship with local media should be a key priority. Journalists love to hear about local businesses and entrepreneurs. Having a good relationship with them can really boost the profile of the company.

Try to reach out also to people who have influence in your industry and can become a spokesperson for your brand. Think Apple and their Evangelist Guy Kawasaki.

Once you get traction (both on the business and raising awareness) you should work on strategies to keep it going, to engage more people, get more content out there and create excitement around what you are doing. 

Build that momentum and keep it going!

Finally, tell us about your new venture you are working on.

I’m currently working on three new ventures. The first two are all about improving the services offered within the property industry both online and offline. The third is about investing in new startups.

I’ve been running my property investment company since 2007 as I’ve seen some pretty horrid business practices. I pride myself on the level of customer service I deliver and there is a lot lacking in the industry.

I’m working on providing a range of services to both landlords and tenants that focuses on their needs and gives them the level of services they deserve. I help landlords build their portfolio and income in a hassle-free way while also making sure tenants get the best service and experience possible, meaning they stay in the properties for long-term as a result.

The new venture will offer property management that does not charge outrageous fees to either party and works on the principle of long term stability for both parties is good for business.

I am also hoping to integrate my network of solicitors, accountants, brokers and builders. They know the industry as they are investors themselves and would be able to work on behalf of my clients at favourable rates while providing excellent services at high standards. 

I’m also passionate about teaching and mentoring especially in regards to property investments and financial literacy. I want to expand the work I am doing through the company, advising others on the best strategy for them and their investments.

The online venture looks at improving the current property portals. These were okay five or ten years ago but they're out-of-date now. They’re not dynamic enough and don’t take advantage of Big-Data's introduction. My idea is to take the risk out of the home buying/selling and to make each step easier and more intelligent.

If you would like to talk more about the topics in this interview or about my new ventures whether you would like to get involved as an Intern, staff member or investor please get in touch with me on LinkedIn or Twitter

Thanks Ryan for sharing your startup insights with us. We wish you great success in your new chapter of your exciting entrepreneurial journey!


What drives you as an entrepreneur?

What is the best advice you received as an entrepreneur?


Mark is a current journalism student in DCU and has covered a range of topics across print and radio. Having taken a class on entrepreneurship, he found startups were the most exciting thing happening in Ireland and developed a keen interest in them. Apart from technology, Mark has a love for biographies and Woody Allen films. You can contact him on Twitter or LinkedIn.

Author: Mark Hogan

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