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Venture Capital vs. Bootstrapping: Kelly Ann Woods of State B On How To Determine If Fundraising Or Bootstrapping Is The Right Choice For Your Startup

Never be undercapitalized — It’s all well and good to bootstrap a company but never think you can accomplish something for less than you have projected it’s going to cost. Cutting corners can get really messy and can get you into a position where you can’t access more capital then you’re really stuck.

Founders are often faced with the nagging question of whether Fundraising or Bootstrapping is the best choice for them. What is better, having access to capital or maintaining full control over your vision and profits? What is preferred, to have the seasoned oversight of an experienced investor, or to plow forward with a disruptive and pioneering ‘can do’ attitude? Of course, every situation is different, but what standards can be used to help a founder decide? As a part of this series called “Venture Capital vs. Bootstrapping: How To Determine If Fundraising Or Bootstrapping Is The Right Choice For Your Startup”, I had the pleasure of interviewing Kelly Ann Woods.

Kelly Ann Woods is an award winning business woman. Entrepreneurship has been in her blood since the early days of a pop up card table concession stand at her mother’s softball games. She is a trained actress, herbalist, sommelier and distiller having made drinks, packaged drinks, performed and spoke all over North America.

Thank you so much for doing this with us! Before we dive in, our readers would love to learn a bit more about you. Can you tell us a story about what brought you to this specific career path?

Great question! I always find the career path questions long and rambling so I will try to be succinct.

I guess it started out when I was a an actress graduating from Theatre school trying to figure out what I was going to do for the rest of my life and how to make money while I was trying to act. I became a flight attendant for Air Canada and I started to see the way the world worked a little bit more and decided that I should become a sommelier so I would have something more interesting to talk to be people about at cocktail parties. I then found myself acting and also very much in the drinks world as a sommelier and mixologist winning cocktail competitions that sort of thing tasting wine building wine lists. My work today very much evolved from my love for botanicals and herbs I owned and operated a craft distillery in the mountains of British Columbia for about 7 years until I sold it and in early 2020, after completing a women’s cannabis business accelerator in 2019, I’ve launched a functional cannabis drink called State B and a functional CBD drink called Elevé and off the side of my desk I’ve been doing research and development on an adaptogenic mushroom drink which could easily incorporate psilocybin depending on how legalization goes. So, a winding thirsty road of drinks and performance you could say.

Can you share a story with us about the most humorous mistake you made when you were first starting? What lesson or takeaway did you learn from that?

It was strange then and then became really not funny and is actually funny now. We had been given investment funding from family to start our business and at that time the bank had been falling all over us to give us more money. We thought we were being smart by flipping them the bird and basically telling them to go away with their money. Of course as we got into business we soon realized that we were way undercapitalized and that in order to compete in any way in the distillery world we were going to have to have a lot more money than that. Unfortunately because we were in so deep at that time those banks that were falling over themselves to give us money at the beginning when we didn’t need it weren’t there anymore.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Strength of character

I would have to say that one of the main characteristics would be strength of character you have to stay strong in your ability to be discerning and use your instincts. Along the way a lot of people will try to drag you down either just because of their own projections or jealousy or whatever you have to stay strong so you can lead your team into success and not lose faith about who you are and what you stand for.


Have perseverance is huge it is so difficult to stay the path when things get tough but you have to remember to rise again you have to remember that tomorrow is another day you have to remember that people have your back. If it was easy everyone would be doing it and it’s not easy but if what you really want to do is build a business or build a brand you have to get up every day and try try again.


Trusting your gut. So much research has come out in recent years where they are literally understanding that your gut is your second brain. And I would argue that your gut is smarter than your brain. Your brain tries to calculate and think but your gut never lies. It’s scary to follow your intuition especially when it’s up against something that your brain is telling you is no big deal or otherwise, but it is always disastrous not to trust it. Trusting your gut separates you from the masses and makes you very skillful in the art of business.

Are you able to identify a “tipping point” in your career when you started to see success? Did you start doing anything different? Are there takeaways or lessons that others can learn from that?

I’m still waiting for it. Ha ha. Just kidding. I think it’s when I started to really honor myself honor myself. Honor my gifts uphold myself, stand up for what I believe in and to allow myself to take up space. I think as women we are trained that it’s dangerous to take up space. Dangerous to speak too loudly. His holiness the Dalai Lama, I think, once said that western women will save the world. There is a real turning point happening right now and I think that women in general all over the world have to learn to take up space. One of my mentors says “we don’t want to fight over the one seat at the table we want all the seats at the table” and it’s when we start thinking that that can actually happen, that’s the turning point.

None of us are able to achieve success without some help along the way. Is there a particular person or mentor to whom you are grateful who helped get you to where you are? Can you share a story about that?

I have to say that the woman that is currently my director of operations, Melissa Stacy, has been instrumental in me getting to where I am today . She came on very early in the project and believed in me and worked as my assistant to really drive and help me grow the business to where we are today. She has since been promoted and she is doing incredible work. If you had just met Melissa or looked at her resume you would have never thought her to be in the position that she’s in today. Sometimes it’s easy to overlook people but I think it’s important to see the value that they bring despite not having certain experience. It goes back to that gut thing. Or that women should take up space thing. Melissa and I met through a food co-op I founded in the small town we live in. I was on a soapbox at one of our meetings one time going on about this or that and I caught her across the room (she had brought her baby to that meeting in fact) I caught her across the room giving me that look like she admired me or she thought I was smart or something and I thought that’s the kind of person I need to have on my team people who believe in me and that I can work with to drive the vision.

You have been blessed with great success in a career path that many have attempted, but eventually gave up on. Do you have any words of advice for others who may want to embark on this career path but are afraid of the prospect of failure?

I think you have to prepare yourself for failure. Because you will fail. You will fail a lot. But the difference between the people that succeed and the people that don’t succeed is the people that try again. That are formidable in their resolve. There are lots of quotes about that! It’s important to get up every day and give it your all and try again. I truly believe that the path will create itself that you will find your way but you have to keep persevering.

Ok, thank you for that. Let’s now jump to the main part of our discussion. Can you share a story with us about your most successful Angel or VC investment? Or an investment that you are most proud of? What was its lesson?

In one of our early rounds I was struggling. I was coming up against not having anymore names in my rolodex and the person who I had hired to help me with the raise wasn’t being terribly helpful. So, I thought to myself, what do I have power ove?. So I did a micro raise. I literally put it out to people on my personal social media network and I offered people a very small amount of equity for a very small investment I mean $10,000 as an entry isn’t a very small investment to a lot of people but in the world of capital fund raising it’s a very small amount. Would you believe that I had probably 10 to 15 people come forward and at the end of the day around 10 people ended up investing and that was to the tune of 100,000. I kept moving the needle. And I engaged people and felt empowered.

Can you share a story of an Angel or VC funding failure of yours? What was its lesson?

I wouldn’t say this is a failure of mine but I would say that it was a really challenging experience. When I had hired someone to help me raise funds that didn’t workout very well. In fact I had a particular situation arise that caused a significant amount of mental anguish. They really didn’t have her sense of what the deal was and miscommunicated a lot with the potential investor . Bottom line is it got really uncomfortable and I was seen in a light that I didn’t really appreciate. I saw the boys club for what it was and it was awful and it took me awhile to recover from that. What i learned is that i need to be in charge of my destiny and again, trust my gut. The red flags were flying but I didn’t listen.

Is there a company that you turned down, but now regret? Can you share the story? What lesson did you learn from that story?

Not yet but I’m sure there will be!

Super. Here is the main question of this interview. Let’s imagine that a young founder comes to you and asks your advice about whether Venture Capital or Bootstrapping is best for them? What would you advise them? Can you kindly share “5 things a founder should look at to determine if fundraising or bootstrapping is the right choice”? If you can, please share a story or example for each.

Number one

Never be undercapitalized

It’s all well and good to bootstrap a company but never think you can accomplish something for less than you have projected it’s going to cost. Cutting corners can get really messy and can get you into a position where you can’t access more capital then you’re really stuck.

Number two

Get money before you need money

The old adage is so true. Money is iaccessible to you and when you don’t need it. But when you need it it is much harder to get. If you go through a process where you’re bootstrapping and your credit cards are maxed it’s very difficult to go to a bank and get a loan it also doesn’t show very well to other investors if you’re really scrambling. Get the money before you need the money.

Number three

Consider equity crowdfunding

Equity crowdfunding has grown leaps and bounds in the past few years. It has created an opportunity for people to buy equity in your company for as little as little as $100 on some platforms. It’s a lot of work but it also doubles as a marketing effort we did this process for a restaurant that we opened and man it was a really hard but a really great experience. It’s an opportunity for your community to stand behind you.

Number four

Do your research

Find out who you’re pitching to. It’s really difficult to have a conversation or to sell your brand to someone and not have any idea who they are what they are doing or even any projects that they are funding. Doing research into who the firm is or who the people are will inform how you approach the pitch session. Know your audience. Figure out who they are and what makes them tick.

Number five

They aren’t necessarily smarter than you

Raising equity and talking to really important people who have a lot of a different vocabulary that you don’t necessarily possess can be really intimidating. But I often think back to Michelle Obama’s quote about sitting at a table and then realizing that the people around her weren’t that smart. Now, I’m not saying that people that hold the money bags aren’t smart I think it’s just important to realize that they may know things about things that you don’t know but you know what you’re doing . I will also add to that that just because someone has one opinion about your project or what you’re up to doesn’t necessarily mean that someone in a meeting the next day will have a completely opposite opinion. I believe it was Fred Astaire when he was auditioning for Julliard, on his audition card the auditioners wrote “shows no promise” well we all know how that turned out.

You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

I believe that in this day and age, companies have to have social responsibility. I don’t believe that corporations should be able to operate without having a gift agreement or some or profit sharing involved with a social equity or My company Brujera Elixirs incorporated contributes 1% of our profits annually to Raven Trust which is an indigenous legal defence fund. We make drinks with plants and botanicals helping the indigenous peoples to protect their water and land rights fits with our fundamental values.

We are very blessed that a lot of amazing founders and social impact organizations read this column. Is there a person in the world with whom you’d like to have a private breakfast or lunch, and why? He or she might just see this. :-)

I am inspired every day by all of the incredible minds and leaders. I simply can’t single out just one. But I would happily brunch with anyone to talk about our dreams and goals and how we are making the business world better for those around us and those coming up behind us.

How can our readers further follow your work online?

Check out our website you can log on to our tick tock Instagram Facebook LinkedIn and all other social platforms from there but more importantly we send out a BI weekly newsletter that’s really how to be in the club with us.

Thank you so much for this. This was very inspirational, and we wish you only continued success and good health!



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