Last week, we published Part 1 of our interview with Judith Clegg, angel investor and founder and CEO of The Glasshouse and Takeout. In this half of the interview, Judith discusses kindness in business, inequality, following your passion and what she looks for in startups to invest in…

“I would prefer to live in a world where we all value each other”

While she’s the first to point out that there’s still a long way to go, Judith is heartened to see a lot of work going into boosting equality in the tech and entrepreneurial sectors…

“Those of us who are lucky enough to come from privileged backgrounds, which by and large most of us living in Western economies like the UK are, then I have a duty to make sure that I stand up and do what I can to help other people who aren’t so lucky.”

“There’s a lot of amazing work happening [in terms of equality], there’s some fantastic female role models. There’s many men that I know, some very prominent men that I know, who make very active efforts to make sure that they either are looking at investing in women or making sure that there’s enough women in senior leadership positions in their companies. After the very sad and untimely death of David Goldberg aged 47 (the pioneer of women’s rights and husband of Sheryl Sandberg) the men who are leading this charge are rightly getting many plaudits. Some of the men support this diversity for ethical reasons but many support for economic reasons alone. They know if they involve a wider group of people in their business they’re going to get better results.

“I’m really heartened to see things like the He For She movement. There’s some amazing men and women who are pushing things forward in the community. I think the first thing is to focus on that and less on the other stuff, because if we focus on the things that we want then more of that will happen.”

“Old fashioned outdated attitudes… just aren’t going to cut it anymore”

On creating a fairer environment in the technology industry, Judith believes we need to tackle old fashioned behaviours and bring a more modern attitude to the tech sector.

“I think part of it is also about the industry becoming more connected with the rest of the world. Now that technology is really disrupting almost every single industry, then it’s become part of the mainstream. Therefore, if you’re going to be working in technology, that’s disrupting the mainstream, then old fashioned outdated attitudes of talking about women badly, or not treating them well (and let’s be honest, they are very old fashioned), just aren’t going to cut it anymore.

“I think it is changing and the things that we can do to help make sure the pace of change continues is women helping each other and helping move the industry forward to being modern, rather than a men or women thing, and also making sure successful women or companies that have got successful women are covered in press or conferences just as much as the more stereotypical tech founders, and I think that’s happening, I really do.”

“It’s more about making it cool and normal for girls to do programming”

Tackling inequality is also about education, says Judith…

“It’s so important that we help our young kids learn to code. I was incredibly lucky that my father in many ways was not a feminist but in many ways he actually was a feminist beyond all of his age group, teaching my sister and I to code… I actually went to an all girls school… it was quite a small year, 7 of us took physics A-level, so about a third of the year group took physics A-level, and I’m pretty sure I wouldn’t have done that in a mixed school. I would have probably tried to do more things to impress boys at that age. It’s more about making it cool and normal for girls to do programming.

“Watching my niece and nephew grow up, they’re both interested in technology from really different angles so I think it’s making sure that the education we have around technology and science has many different facets to it so that you can be drawn in from lots of angles.”

“You’d better not leave it too late, you have to follow your passion”

Judith’s family have always been supportive of her career and she has learned a lot from them, including how important it is to follow your passion…

“[For] my Grandfather, being an entrepreneur was considered to be low status in his day and age. He was a great sailor and there was a sailing club and a yacht club in the town he loved to be in, and the ‘yacht’ club wouldn’t let him join because he was considered to be a low status tradesman. In my family, being an entrepreneur was considered to be a good thing rather than perhaps something that was low status, so I think I’m very lucky like that.

“My grandfather and father both died very young and my father had had corporate careers and then had more recently set up his own business following his passion. When he died very young, I think that was a lesson to me, which was that you’d better not leave it too late, you have to follow your passion.”

“The more that I do in investing, the more I realise that its about the team”

While experience, traction and great ideas come into the decision whether or not to invest, Judith believes the key thing to look for is a great team…

“I’ve invested or been a shareholder in a few content and enterprise businesses, and I’m continuing to learn and improve my insights in these areas. When investing I find that for it to work for the founding team and me it has to be in an area that you understand and therefore can make some kind of an informed decision.

“The more that I do in investing, the more I realise that it’s about the team. That’s the team of other angels that you’re investing alongside. Do you believe in them? Are they smart people? Are they also going to help the startup? And the team itself, have they got what it takes to really hustle and make that business work?

“If I think back to some of the best entrepreneurs that I’ve been lucky enough to work alongside, then some of them have been more experienced, the serial entrepreneurs. They’re the ones that, as an angel, are just a pleasure to work with because if they want an introduction, you give them the right introduction and before you know it they’ve got the meeting, they’ve done the deal and they’re able to take the support and network that you can bring to them and really turn it into something.”

It’s not all about experience though, notes Judith…

“I remember meeting Harjeet Taggar, who later became a partner at Y Combinator. When he was 17 or 18, he used to come to The Glasshouse events and I could tell, the minute I met him, this guy is going to really build something special because he just had something about him which was that you knew he was never going to give up and he was clever about working and making bold decisions and making sure he and his business were in the right place to take the opportunities.”

Judith says she can look past traction in early stage startups if she sees something special in the team and can understand how they could get their business to work

“Team is a thing I would look at most of all. If they haven’t got traction, is there a reason to believe that they can get traction? Has this type of disruptive business model worked in another sector and is there a reason why we think it could work in a new sector? If they’re after a new sector, have they got access to the right networks to be able to get them to meet the right customers? If it’s an enterprise business or if it’s a consumer business to really, really understand what that consumer wants and how are they able to keep changing the product until they get it right. Is the team resilient?”

When discussing the kind of people, she likes to work with, Judith points out some of the most important characteristics that the Takeout team are always on the lookout for…

“[Valuable characteristics include] high quality work, going the extra mile always, positivity, kindness – are they able to put themselves into someone else’s shoes, whether that’s a customer or a coworker or someone else in the community, and empathise and modify something in their own behaviour as a result of that and actively contribute. We also look for humility, obviously you don’t want people to be so humble they’ve got no confidence but I think humility actually does come with confidence. We also ask every prospective team member “what do you do to help other people outside of your family and your work?” We take their responses very seriously indeed.”

While she has been known to turn away some investment opportunities quickly, Judith notes that being turned down doesn’t necessarily mean that an investor doesn’t believe in your business.

“You can tell [whether you want to invest in someone] relatively easily from the way someone communicates and speaks with others. You can tell some things about their character or from their research. Even if somebody wasn’t relevant to me, they might be really amazing, but maybe it’s not a sector I’m interested in or I can’t add value to, then I’m probably just going to cut the conversation relatively quickly so as not to waste anybody’s time. It doesn’t mean to say the business couldn’t be amazing, its just not the right fit for me.”

“Build your network with other entrepreneurs and founders”

Like many investors, Judith prefers to work with ones that she knows and trusts, but will take a risk and invest in a startup others don’t believe in if she feels it’s right.

“There’s a group of angels that I know and I trust their opinion. If we all agree it’s a good opportunity, I’m more confident about that investment… I could question myself more if it was just me who thought it was a great opportunity, but that doesn’t mean to say I wouldn’t still invest in something I really felt sure I could see something where other people couldn’t. I think making sure that I’m around other smart, questioning minds and putting all of our brain power together, those angels I trust, well, I’m always interested to hear their opinion and merge it alongside mine to make my final choice.”

Building a solid network is key, not only for support, but to get introductions to investors says Judith.

“It takes time to get to know people so I think it’s important to take proper time as needed and to really stress test things. That’s why I think you’ll find a lot of angel investors and institutional investors will often like to make sure that they’re introduced to investment opportunities through someone in their trusted network who also says they rate these people.

Whilst I think it’s important for investors to look outside their networks for entrepreneurs and make sure that they see companies with a diverse set of founders, I do think that building trust between an entrepreneur and angel is incredibly important. I think a really strong piece of advice for entrepreneurs looking for investment is to make sure you build your network with other entrepreneurs and founders so that when you want to be introduced to investor that you don’t know, that the person introducing you can honestly vouch for you. And that’s where the things like always doing high quality work, always behaving with ethics, always doing things to help your community come back.”

“Building technology to make the world a better place”

“The tech sector when it founded, one of the reasons that I really liked it, was this idea of building technology to make the world a better place and this pay it forward culture that was very strong in the early part of the tech community. I think with clusters, the more we can do to help each other pay it forward, I think the more successful businesses in technology will be. For example, at Takeout, we give 10% of our revenue to our charity LiveKind and I think there’s a really exciting set of modern business people who believe that doing their piece for their community is actually really smart business.”

Make sure to check out part 1 of the interview where Judith talks more about how she got started, dealing with startup stress and kindness and equality in business. You can follow Judith on Twitter @JudithClegg.


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