Growing a business = Endless Outreach

There was a record number of businesses started in the 2020 pandemic. As of mid-September, business applications nationwide are up 19% year over year, according to census data. It was also my first complete year of running my own business - and I learned a lot. After years of thinking about running my own show, I pulled the trigger with Ballast Advisory.


This was the year of the hustle for me. I learned a whole lot and adjusted my positioning several times to get to where I am now. I’m a sucker for a retrospective so I thought it would be helpful to pull back the curtain.

Research and Make connections

Based on the business that I’d like to build, one of my goals is to get closer to the investment teams. Getting accepted/invited to the Underscore VC Core was absolutely huge. I am thrilled by this and can’t wait to dig in.


Some of the outlets that I use to research/cultivate relationships:

  • Nick Stuart’s newsletter → Boston centric content. He always seems to highlight the funding news before other Boston publications hit them. I once congratulated a founder about a funding raise before it “hit the press”.

  • Leo Luo’s newsletter → Highlights super interesting consumer startups. Does a wonderful case study style breakdown of a company’s product story and interviews an investor.

  • MassTLC → This wasn’t as successful as I would have liked it to be - but it is still early. Their community base is built around larger companies so it isn’t as tuned to someone like myself (company of one).

  • The Buzz → Focuses on startups that are looking for help. As someone looking to get involved in boards and advisory boards, this letter is helpful although hasn’t yielded any leads.

Endless Outreach

LinkedIn is the worst and the best. It is the best because you can learn so much about someone very quickly. It is the worst because if they don’t write back to your note, you can’t email them again. It’s like living in timeout purgatory hell.


Halfway through the year I reached out to an old friend, Colin Kindgren, for some advice on sales pitches. This was one of the most helpful chats of the year. Essentially, expect absolutely nobody to respond and whenever possible send an email over a DM.

There are some people on my list that I really wish had responded - not because I want to sell them anything…. but because I just truly love the companies they are leading:

  • Aubuchon Hardware → oldest family owned chain of hardware stores in America. Massachusetts based and founded in 1908 with 104 stores. I believe they are beating the competition in terms of timely targeted email marketing, COVID safe shopping experiences, and delivering customer satisfaction. Their site search initially caught my attention as it was really solid and better than Ace Hardware. Current CEO is Will Aubuchon

  • Fi Collar → NY based. GPS dog tracking. Discovered after wildly subpar experiences with Whistle. Loren Kirby is the CTO and co-founder. Loren was also employee #20 at Dropcam/Nest (another one of my favorites). I do not understand why every dog owner does not have one of these. It’s the most affordable form of “insurance”.

  • SnackPass → SF based. A food app that focuses on ordering, not delivery. Social dynamics are super imbedded into the experience in a collaborative way. Would love to hear more about their user behavior and what changes they’ve made along the way. Kevin Tan is the CEO.

  • Eversound → Boston based. An engagement solutions company that helps senior living communities combat social isolation. I’ve seen the impact that hearing deficiency and loss can have and believe really strongly in the future of what Eversound is delivering.

Others on my list to try and befriend?

  • Peapod Digital Labs → Chicago/Boston based. Online grocery has exploded. How can an established player like Peapod compete with Amazon?

  • Thrasio → Boston based. Top 25 seller on Amazon via acquisitions. Wayfair was one of my favorite roles ever and ecommerce strategy is an addiction for me.

  • Carewell → Charlotte based. e-commerce company with a mission to improve the lives of caregivers and their loved ones.

  • Vice Ventures → Brooklyn VC firm that invests in “bad” industries like cannabis, addiction recovery, etc.

  • Dynocardia → Boston based. Continuous blood pressure monitoring wearable

  • Dock Health → Boston based. HIPAA compliant to-do list for healthcare teams

  • Well → Chapel Hill / Boston based. incentivize inspired plans to achieve personal health goals… with doctor created plans.

In all of this I’ve used Hubspot to manage my research and connection history. It has been such an amazing tool for scheduling meetings, contract tracking and action follow-up - and completely free. More to come.

Are these problems that you are trying to solve for your business? Or maybe you just like to talk about eCommerce and digital strategies? Let’s talk.

This post can also be found on my Substack.