Attracting Angel Investors & Managing A Start Up

Will Paxton, Sailor and Sail Maker

I had worked in start ups when my children were small. After I had my second daughter I quit my full time job as a Marketing Director at a music software company. It was a steep cliff, but I had a baby and a two year old and working 90 plus hours a week was no longer tenable. I never went back to traditional full time work. Instead, I worked as a consultant for start ups. So I knew exactly what I was getting into when I started my own company.

Companies need more than money when they are starting out, but seed money is a must at the onset. I had sat in plenty of pitch meetings and we closed a good deal of investments, so I knew what I was doing.

People will tell you raising money is difficult. Is it? That doesn’t make sense when the business publications report millions even billions in investments annually. So, let’s begin with the idea that raising money is easy. Move forward with that notion. But not all money is good. My first investment was from a close friend I met in college. At the time I was desperate to get my fabric out of Thailand. It is never good to be desperate and looking for money. This is now a rule of mine. However, at the time I felt I had no choice and took the money.

I’m not ashamed to admit this was a period of my life when I operated out of fear. My husband had just died suddenly of a heart attack and I had two kids in high school heading to college. I had a nice chunk of money in the bank that I was afraid to spend, therefore, I was looking for a way to dilute my risk. I believed this was the savvy way to approach my business. By believing I was sharing the risk I was also committing to the possibility of failure. In the end that investment cost me many things, but most importantly it almost cost me a very close friendship. Apart from the friendship that spent two years on the rocks, it cost me greatly in both time and money.

My next investor I found through writing about my company. At the time I was writing a local column for free. I wrote about my life and my business. Never underestimate the power of adding value and sharing what you have to give. In my column I shared my wisdom and experience. How this ended 2 years later is another column. But, writing for free opened the door to a great opportunity that I not have gotten otherwise. I closed this round at a nearby coffee shop in one hour. This was the perfect investor. He provides me with support of all kinds. He is truly an angel.

One of my favorite sayings is:

Giving and gratitude are hallmarks of success.-Unknown

At every opportunity I make it a point to give. I give 10% of every sale I make to one of my ocean causes. At the end of the year I pulled out my check book and sent small donations to my Alma Mater, the San Fransisco Ballet and Santa Maria the little church I love in Orinda, California. But, I also give of my time. I write a column Medium and I write on my blog. I teach a class at UC Berkeley and I make it a point to build connections with my students and this takes time. I provide as much value as I possibly can. If I had not agreed to write the column without being paid I would not have found the investor that has kept my dream alive. Give. Give. Give.

At the end of January of 2020 prior to the pandemic I pitched Silicon Valley Forum in San Fransisco. I wanted to raise 1.5M for inventory and advertising. From this event I met two new business partners that helped me grow my business. I had investor inquiries and then the world as we knew it stopped. I sat in my back yard and cried. When I started Ocean SF my husband died suddenly. He was in perfect health, went to work and didn’t come back. My first prototype had just arrived. I was setting up my website. My future looked amazingly bright and then it didn’t. In 2020 it happened again. The expectation on both occasions was “Well, that’s the end of that.” As I sat in my backyard my phone rang interrupting my moment of despair. This friend told me not to worry that it was just a matter of time before my brand took off and that I should take it as a blessing that I wasn’t further along with stores across the country like other retailers.

David Janinis wearing Ocean SF

Even though retail took an enormous hit I persevered. In 2020 I did another production run of my signature jacket and was able to sell most of it, now I am working on my cotton series. My work employs many other people and I am able to keep my sample makers busy and my factory running. Although sales were slow in 2020, I did make sales. Some of them I hand delivered, but every day when I took orders I was grateful. I am thankful for what I do have and that I have the capital to continue to pursue my dream of sustainable sailing apparel.

Additionally, there is another kind of capital that is worth more than money. In 2020 I spoke to a business coach who told me to remove anyone from my life who did not support my business. There were a few people close to me who really didn’t want to hear about Ocean SF and they certainly didn’t buy or wear my clothing. Just like we have to sort through our closets and remove the things that do not serve us, so it is with friends and family. I put these people on the back burner and brought into focus those who believe in me. My two biggest fans are Brad Helms and Will Paxton (pictured above top) offering countless thankless hours helping me with my photography and wearing, promoting and buying my clothes. Other major supporters are Craig Nomura who advises me on every detail of the business and David (pictured middle) who wears all my clothes and models for me. As I move into 2021 these are the people and countless others that I hold close because they are worth more than their weight in gold.

If you want to raise money do not operate out of fear and desperation. Give of your time and talents as the world is a circular economy. Surround yourself with only those that believe in your dreams and support you 100%. Ask for help. What we may think is a chore, others find a pleasure. It feels good to help other people and the people around you want to help you. Ask for help and most importantly give it.

Never ever give up.

Love and blessings.

Sydney Chaney-Thomas

Sydney is an entrepreneur, mother, artist and writer. Founder of, a sustainable sailing apparel brand.

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