Welcome to Bolster Prime

I’ve spent almost my entire career as an entrepreneur. My first three jobs were not directly entrepreneurial. Or were they? If I’m honest - my first jobs were as a teenager. I was always starting something and making plans so that I could learn and have the independence that I have always craved. As a middle-schooler, I started a babysitting and birthday party business and just rolled into high school teaching flute, selling calligraphy services and doing graphic design work for people. I also worked plenty of hours at a restaurant but I was always scheming.

When I went to college, my first job there was in the dining hall. I quickly became the student manager and then decided to open a dessert cafe called Late Night Bites, so I continued my entrepreneurial tendencies. And while it was 6 years from the time that I graduated from college to the launch of my first startup, I learned a lot from many wise people along the way. My first father-in-law was an entrepreneur, and the last company I worked at before starting my own was founded by the early computer pioneer, Bill Poduska.

When I started my company - Net Daemons Associates - my then husband told me that I didn’t know what I was doing and was concerned about what would happen to us. We had a one-year old, I made twice what my husband did and it felt a bit tenuous. I’m not a big fan of being told that I “can’t” do something, so I figured out how I could.

The truth is that I knew not thing one about running a business. I could not have told you where the revenue line was from the net income line or what expenses were or … you name it, I didn’t know it. My co-founder was about the most technical person that I knew, and if anything felt like rigor or business and wasn’t code or managing UNIX networks, then he’d literally almost lay down and hope that moment passed. Luckily, a really good friend of mine did know something about business - at least about being an accountant! And he was the first mentor that I went to so that I would have someone to help decode what I had started.

I bootstrapped a consulting business with one customer already “signed” and no money in the bank to support us. This was 1991 and the world wasn’t rife with VC and angels and debt wasn’t “a thing” and we still wrote checks and didn’t have mobile phones or ATM cards or … the internet. And so, in order to learn, I had to find people who knew more than me so that I could learn what they did.

From my friend, Rudy, who became our CFO, I met Russell. Russell was a corporate lawyer, he had his own practice and he became our lawyer. We hired some people who knew some people and they had expectations about how they thought work should “work” and so I kept seeking out people so that I could keep learning and growing. When we got our first office, we were just down the hall from another startup. The people in this startup knew that they were a startup - they were MIT graduates and had cut their teeth by working for other startups in Cambridge, MA and so they knew the words, people and the concepts. We put our heads together and realized that if we all put our collective wisdom together, we’d most likely do better at what we were building, so we started something called the e-dinner. We were all working in high tech, in the heady days of just before, during and right after the internet “happened” and we were all in the middle of that tornado because we were all computer networking geeks. And, I met so many people who changed the course of my life through the e-dinner.

We got together once a month, shared our experiences and successes and failures, networked and grew from our collective pooled knowledge. We were greater than the sum of our parts by many. And from this group of people, I met Brad Feld who had a company that he eventually sold to Ameridata. Brad Feld’s sale of Feld Technologies changed the trajectory of so many of the e-dinner people. When Brad sold, he started investing first as an angel and then as a VC and changed the course of so many. Midnight Networks, net.genesis, Interliant (originally Sage Networks) and so many more.

I don’t really need to complete the story to get to the punchline. I would not be the person today if it weren’t for the people that I met along my entrepreneurial journey. Within a year of starting Net Daemons Associates, I had a paid advisory board of mentors that carried me through many stages of my professional journey. They helped me learn what I didn’t know, opened many opportunities for me, saved me from countless disasters and were there when things were high and things were low. They shared their wisdom and I shared mine.

The experience that I had as I started my company, as my then husband was telling me that I couldn’t and that I would fail, was profound. And, it put me on a path for the rest of my professional journey where I have always made sure to share my experiences for the benefit of others; to put my hand on the back of people who need support whether they know it or not; to invest when I can; to be there for the good, the bad and the ugly; and to share in successes and decode failures.

This is a long preamble for me to talk a little bit about what I am working on at Bolster. I’ve spent most of the second half of my career in positions that are in service to startup or first time CEOs. I love this role so much that I want to understand how I can better help startup CEOs learn the craft of being a CEO and find a way to programmatically pair startup CEOs with mentors so that they can grow themselves further, faster and increase the value of their startup.

After I left Techstars, where I was the COO for four years, I found that I had a little bit of a hole in my life which was the opportunity to engage with startup founders on a daily basis. Techstars does an amazing job of getting a founder from idea to build and flips the failure success metrics on their head through strong support and mentoring at a foundational time in a founders’ journey. What I also found was that “and now what” was a common issue that founders faced and also where I wanted to be able to bring resources to bear. There are so many opportunities in life where you can look back and say “if I hadn’t had … then …” and joining Bolster is one of those times. During the first wave of the pandemic, I reached out to Matt Blumberg after realizing that he lived somewhat nearby to find out what he was up to and learn more about his new startup, Bolster. Matt and I have known each other for years and we go way back through the Brad Feld network and keiretsu years, but we hadn’t spent any real time together. We met a few more times and we found alignment in my passion to help entrepreneurs on their scaling journey with both mentoring and capital and Bolster’s mission to help entrepreneurs succeed through addressing their talent and capital needs. Recognizing that I’d move faster and see more traction in joining Bolster on their mission, I joined Bolster and we’ve been busy this past year!

I couldn’t be more thrilled to see Bolster Prime and Bolster Ventures launch. Bolster Prime is a complete amalgamation of what I have been working toward since I was that 28 year old, first time, female entrepreneur. I know through deep experience that you can grow further, faster, on the shoulders of giants. And, I also know that those giants don’t have to be household names or headline grabbing companies but simply people who are humbly willing to share their experiences, open up their networks and lean in so that another person can learn the craft of being a CEO and a leader. And that’s what Bolster Prime is - a recipe of a startup CEO + a Bolster Prime Mentor + foundational content + talent marketplace all coming together to drive scale and value, further and faster.

It’s always been on my bucket list to be a VC - it’s one of the last things that I’ve come around to. Bolster Ventures invests in those startup CEOs who see the value in having a strong mentor and believe in access to content, talent and people who have xray vision into the future. It invests in the Bolster Prime clients who are scaling and need a little extra capital to advantage them just a bit more. Bolster Ventures is a $6m early stage venture fund that will co-invest in select Bolster Prime clients with one-time, $100,000 investments.

If you are a CEO who loves to learn, believes that you can learn from someone who has “been there, done that” and wants to not just grow but scale your startup so that you can drive value further, faster, check out Bolster Prime.

-Jenny Lawton, February 9, 2022.