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Tips for Entrepreneurs from a First Year VC

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A close friend of mine likes to joke about how entrepreneurs & operators who become venture capitalists are “trading in their blue light sabers for red ones” – it’s a funny analogy…naturally, comparing investors to Sith Lords seems to fit pretty well some days.

But the benefit of switching from one side to the other is that perspective can sometimes be illuminated. After nearly 20 years of operating at places like Mozilla, Reactivity, Trilogy & Apple, I still tend to think like an entrepreneur myself, so some of the assumptions of life inside a VC are maybe a little more obvious to me than folks who have been around longer.

So here are some observations about my first year of VC life, and then some of the ways that being on the “inside” has changed the way I think that entrepreneurs should think about approaching investors – things I wish I had understood myself when I was pitching.

A Year of Observations about VC Life 

Life as a VC is a sea of meetings. Really, it is a lot of meetings. Most of them are single meetings, with no follow-ups. Most don’t result in an investment in a company at all. In 2011 I had first meetings with just over 350 companies, plus another 100 more as parts of business plan judging and demo days. Those meetings resulted in just four investments for me (Tumblr, Dropbox, Clearslide and Citrus Lane) plus a handful of seed investments.

That’s a massive “bias-to-no” for any profession – 99% or so. It’s a tough negative bias, and every investor I know is affected by it in some way. But that one percent is like a lightning strike: those meetings can form the basis for some of the most interesting and meaningful work you’ll ever do.

High fidelity communication is impossible. Because so many meetings are one-offs like I described, it’s very hard to communicate effectively. As an operator, you get good at being direct with the people you work with – or you fail.

In the context of a startup, relationships are developed over a period of months or years, so that candor can be better understood and more nuanced, resulting in communications that are efficient and effective, without hurt feelings from misunderstandings.

Venture meetings aren’t like that. They’re incredibly overloaded: you’re trying to have a really good communication about who you are, what you’ve built, and how you want to grow. And you’re trying to do it in what is very often an extremely emotionally significant context of someone putting everything at risk to change the world. All with no existing relationship context to fall back on.

As an investor, I feel that a situation like that deserves my fullest possible attention, and my best questions about and suggestions for the business. But since we’ve never interacted before, there’s the danger of seeming too harsh in cases like that – we don’t have the shared context, vocabulary and trust frameworks in place that you do in longer term relationships. I think that’s why so many investors are often vague or non-responsive in their interactions afterwards – something I’ve tried very hard to avoid, although with imperfect success so far.

Timing is everything, and everyone is multi-tasking. This applies to both the startup and the investor I’ve found – because each has their own set of work going, and any number of competing projects and priorities. The right thing coming by at the wrong time can be as challenging as an investment that just isn’t a natural fit. Life as a VC has different patterns and rhythms than life for operators – the nature of VC work is that you’ve got multiple companies and entrepreneurs you’re working with all the time, plus a constant stream of new folks to meet, and often in wildly different domains.

This means constant context switching, and there are times when excellent entrepreneurs and startups come through when it’s just hard or impossible to take focus from existing or in process investments. That creates a severe asymmetry: as an entrepreneur, you’re thinking about one thing (broadly defined as your startup), deeply,all the time, while investors that you’re talking with are trying to juggle many at once.

Venture firms and partners are idiosyncratic and highly personal. When I raised money for my own startup, I didn’t know much about how to think about approaching VCs. I knew folks at various firms, and mostly went to talk with those who I knew and then went through their process over the subsequent several weeks. I figured that VCs were all mostly similar to each other.

I’ll say candidly that in my case, I was extremely lucky when that “strategy” worked – my investors were Mitch Kapor and Peter Fenton when they were both at Accel Partners – they were incredibly great for us, and I’ve had fantastically productive relationships with both for more than a decade now. But at some level it was really just dumb luck. I could easily have found a firm and partners who wouldn’t have worked.

Every firm has different culture: some are collaborative, others more solo practices; a small few (including Greylock) consist of former or current entrepreneurs, other firms consist of people who have been investors most of their careers; some are progressive, some are conservative. And even in partnerships, everyone there is different. Different in interests, skills, capabilities, stage in life, and temperament, at the very least.

But here’s the thing: meeting with an amazing entrepreneur can change your whole year. 

That’s why you do it. To find people to change the world with. I’ve been very lucky this year to work with some incredible entrepreneurs and teams, not just limited to the companies we were able to invest in. And that’s what we’re all looking for: not just the opportunity to make great investments, but the chance to work with people who are setting out to make the world the way they want it. There’s no more optimistic and hopeful endeavor, and it’s 100% addictive.

Suggestions on Interacting with VCs

Given that context on what it’s like to be on the inside of a VC firm, here are some things I wish I had understood when I pitched myself.

  1. Be human; be yourself. Be prepared and have a pitch, but be willing to go off script. Talk about the parts of what you’re doing that are the most exciting to you! And in general, it’s probably best not to just jump into a PowerPoint deck. Take a few minutes to introduce yourself, and hear a bit from who you’re seeing. Don’t get too informal, of course – you’re still in a business context – but try to interact in as authentic a working style as you can.
  2. Seek out investors who lean forward, who engage, who ask you tough questions. Tough questions aren’t always fun, but they’re ultimately what makes your company better.
  3. You should ask questions, too, particularly to understand how the investor thinks about businesses like yours. I personally love getting questions and like a spirited debate. Helps us get to know each other.
  4. Be resilient. A “no” from a few partners or firms doesn’t mean you won’t get funded. As mentioned above, a lot of times it’s context.
  5. Be persistent. A “no” on this round doesn’t mean that an investor won’t be better, or more able to work on your company in the next round.
  6. Remember that relationships are progressions. Don’t read too much into any particular interaction. Some investors ask a bunch of questions in first meetings. Some listen more and engage more as the process goes on. Everyone is different. When in doubt about what they’re thinking, ask!
  7. Above all, don’t think of fundraising as a transaction to get finished and move onto the next thing. It is important to get the funding you need, but you’ll live with your investor for the life of your startup (and really beyond, relationship-wise). Think about it like the balancing act when you’re trying both to attract and evaluate an all-star member of your team.

Your mileage may vary, of course. But hopefully this bit of context will make the difference for you between just a pitch meeting and the start of a world-changing new relationship.

This article was written by John Lilly, a partner at Greylock Partners. Prior to Greylock, John was CEO of Mozilla, makers of Firefox. In addition to leading Greylock’s investments in Tumblr, Dropbox, Clearslide and Citrus Lane, he’s also on the boards of directors of Mozilla and Code for America. He has written articles for Pandodaily, as well as maintains his own blog.

Entrepreneurship

Women on Top in Tech – Tara Velis, Growth Hacker and Digital Innovation Strategist

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(Women on Top in Tech is a series about Women Founders, CEOs, and Leaders in technology. It aims to amplify and bring to the fore diversity in leadership in technology.)

I am talking to Tara Velis, Growth Hacker and freelance Digital Innovation Strategist. Tara was selected and recognized by TheNextWeb.com as one of the 500 most talented young people in the Dutch digital scene during the 2017 TNW edition. Tara is known for her creative, entrepreneurial spirit, which she is using to her advantage in leading the change in SMEs and corporates around the globe.

What makes you do what you do?

I tend to see life as a big, complex puzzle. Because of my curious nature, I am in constant development, looking for new angles and new approaches to business problems. Innovation through technology is exploring ideas and pushing boundaries. The most radical technological advances have not come from linear improvements within one area of expertise. Instead, they arise from the combination of seemingly disparate inventions. This is, in fact, the core of innovation. I love going beyond conventional thinking practices. Mashing up different thoughts and components, connecting the dots, and transforming that into something useful to businesses.

How did you rise in the industry you are in?

I consistently chose to follow my curiosity, which has led me to where I am today. If you want to succeed in the digital industry, you need to have a growth mindset. Seen the fact that the industry is evolving in an astoundingly quick rate, it’s crucial to stay current with the trends and forces in order to spot business opportunities. I believe taking responsibility for your own learning and development is key to success.

Why did you take on the role of Digital Innovation Strategist?

The reason for this is twofold. On the one hand, I got frustrated with businesses operating in the exact same way they did a couple of decades ago. Right now we are in the midst of a technology revolution, and the latest possibilities and limitations of cutting-edge technologies are evolving every single day. This means that companies need to stay current and act lean if they want to survive. On a more personal level, I noticed that I felt the need to use my creativity and problem-solving skills to their maximum capacity. In transforming businesses at scale, I change the rules of the game. I love breaking out of traditional, old-fashioned patterns by nurturing innovative ideas. This involves design thinking, extensive collaboration and feedback, the implementation of various strategies and tactics, validated learning, and so on. I get a lot of energy from my work because it is aligned with my personal interests.

Do you have a mentor that you look up to in your industries?

Yes, I look up to Drew Boyd. He is a global leader in creativity and innovation. He taught me how to evaluate ideas in order to select the best ones to proceed with. This is crucial because otherwise,you run the risk of ideas creating the criteria for you because of various biases and unrelated factors. He also taught me a great deal on facilitation of creativity workshops.

How would you describe your leadership style?

I tend to have the characteristics of a transformational leader. People have told me that my enthusiasm and positive energy is motivating and even inspiring to them. Even though I take these comments as a huge compliment, I am not sure how I feel about referring to myself as a leader. To me, it still has a somewhat negative connotation. I guess I associate the concept with being a boss who’s throwing around commands. But if a leader means listening to others and igniting intrinsic motivation in people, then yes, I guess I’m a charismatic leader.

Do you consciously or unconsciously support diversity and why?

Yes, one hundred percent. I believe that creativity and innovation flourish when a highly diverse group of people bounces ideas off each other. Diversity in terms of function, gender,and culture is extremely valuable, especially in the ideation phase of a project, as it can help to see more possibilities and come up with better ideas.

Do you have any advice for others?

Yes, I have some pieces of advice I’d like to share.
First of all: Develop self-awareness. You can do so by actively seeking feedback from the people around you. This will help you understand how others see you, align your intentions with your actions, and eventually enhance your communication- and leadership skills.

Surround yourself with knowledgeable and inspiring people. They might be able to support you in reaching your goals, and help you grow both personally and professionally.

Ask “why?” a couple of times. This simple and powerful method is useful for getting to the core of a problem or challenge. Make sure to often remind yourself and your team of the outcome of this exercise to have a clear sense of direction and focus.

Data is your friend. Whether it’s extensive quantitative market research or a sufficient amount of in-depth consumer interviews (or both!), your data levels all arguments. However, always be aware of biases and limitations of research.

Say “Yes, and…” instead of “No”. Don’t be an idea killer. Forget about the feasibility and budget, at least in the ideation phase. Instead, encourage your team to generate ideas without restrictions. You can compromise certain aspects later.

Prioritization is key. There is just no way you can execute all your ideas, and, quite frankly, there is no point in trying to do so. Identify the high potential ideas and start executing those first.

Encourage rapid prototyping. Don’t wait too long to experiment, launch, and iterate your product or service. Fail fast and fail often. Adopt an Agile mindset.

If you’d like to get in touch with Tara Velis, please feel free to reach out to her on LinkedIn: https://www.linkedin.com/in/taravelis/

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Callum Connects

Marek Danyluk, CEO of Space Ventures

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Marek Danyluk has a talent for assessing the competencies of management teams for other businesses and pulling together exceptional teams for his own businesses!

What’s your story?
I am the CEO of a venture capital business, Space Ventures, which invests in seed and pre-series A businesses. I also own and run Space Executive, a recruitment business focused on senior to executive hires across sales, marketing, finance, legal and change.

My career started as a trainee underwriter in the Lloyds market but quickly moved into recruitment where I set-up my first business in 2002. The business grew to around 100 people. I moved to Asia in 2009 as a board member of a multinational recruitment business with the mandate to help them scale their Asian entities, which helped contribute to their sale this year, in 2017.

My main talent is assessing the competencies of management teams as well as building high performing recruitment boutiques and putting together exceptional management teams for my own businesses.

What excites you most about your industry?
Building the business is very much about attracting the best talent and being able to build a culture which people find invigorating and unique. It’s an exciting proposition to be able to define a culture in that regard and salespeople are a fun bunch, so when you get it right it’s tremendous.

From a VC point of view there is just so much happening. South East Asia is a melting pot of innovation so the ideas and quality of people you have exposure to, is truly phenomenal. The exposure in the VC has taken me away from a career in recruitment. Doing something completely different has given me a new level of focus.

What’s your connection to Asia?
Whilst I came here with work, both my boys were born in Singapore and to them this very much is home. That said, my father in law spent many years in the East so coming and settling here was met with a good degree of support and familiarity.


Favourite city in Asia for business and why?
Possibly Hong Kong. It’s the closest I’ve been to working in London. Whilst there are massive Asian influences people will work with you on the basis you are good at what you do and work hard. I find that approach very honest and straightforward.

What’s the best piece of advice you ever received?
“Always treat people well on the way up!”

Who inspires you?
I like reading about people who have excelled in business such as Jack Ma, James Kahn, Phil Knight, Sir Richard Branson, Elon Musk, all have great stories to tell and they are all inspirational. No-one has inspired me more than my parents and they are well aware as to why…

What have you just learnt recently that blew you away?
Pretty much any technology innovation blows me away.

If you had your time again, what would you do differently?
Whilst it is important not to have regrets I do continually wake up thinking I’m still doing my A’ Levels. So, I’d have probably tried a little harder in 6th form.

How do you unwind?
I like the odd glass of red wine and watching sport

Favourite Asian destination for relaxation? Why?
Japan skiing. I love skiing and Japanese food and it’s a time when I can really enjoy time with the wife and kids. I recently tried the Margaret River which was divine, although not technically Asia.

Everyone in business should read this book:
Barbarians at the Gate

Shameless plug for your business:
Space Executive is the fastest growing recruitment business in Singapore focused on the mid to senior market across legal, compliance, finance, sales and marketing and change and transformation. Multi-award winning with exceptional growth plans into Hong Kong and London this year, and the US, Japan and Europe by the end of 2022. We are building a truly global brand.

Space Ventures is interested in any businesses that require capital or management and financial guidance or any or all of the above. We have, to date, invested in on-line training, food and beverages, peer to peer lending platforms, credit scoring as well as other tech and fintech start-ups. We are always interested in hearing about potential deals.

How can people connect with you?
[email protected]

Twitter handle?
@Spaceexecutive

This interview is part of the ‘Callum Connect’ series of more than 500 interviews

Callum Laing is an entrepreneur and investor based in Singapore. He has previously started, built and sold half a dozen businesses and is now a Partner at Unity-Group Private Equity and Co-Founder of The Marketing Group PLC. He is the author two best selling books ‘Progressive Partnerships’ and ‘Agglomerate’.

Connect with Callum here:
twitter.com/laingcallum
linkedin.com/in/callumlaing
Download free copies of his books here: www.callumlaing.com

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