Favorite companies and market opportunities

Each of the past three years as an emerging investor I’ve published a post on the companies I would include in my portfolio; assuming they would take my money and reasonable deal terms.

This year I’m adding a new component: opportunities I want to fund which will be gaps I see in the market at the time of writing

Update on previous companies


Three companies were acquired: ROIKOI, ClearFactr, and WeFind. Unclear terms but likely some level of liquidity. Density and GoPuff raised mega-rounds and are both the talk of the startup town.


Lambda Scool is a well-capitalized pioneer and leader in their market and by many accounts the defining company of the category. Upgraded was acquired by Ticketmaster and Udelv is partnering with Walmart


All are alive and kicking but still in relatively nascent stages.



A company with an asterisk means I am either an investor in or have worked with as a consultant.


Avenify is a marketplace lending platform for Income Share Agreements

Higher education is very much broken. The main underpinning of the issue is a flimsy funding model that requires a tremendous amount of debt or a mid-six-figure price tag to get to a completed degree. What I find most ridiculous is that there is a huge disconnect or lack of alignment between the success of an individual, most notably the job they earn upon graduation, and the institution. Excluding future donations, the school has no financially vested interest in the success of students after they have been paid. If the graduate works for minimum wage or multi-million dollar salary the school as a business is paid the same. This is where income share agreements or ISAs provide novel value. The school and the student are aligned towards an outcome that is mutually beneficial. Avenify is building a marketplace for ISAs with an initial wedge focused on nursing schools.


The New Standard in Print-On-Demand

Dreamship runs a print on demand network which serves as a back office of sorts for many builders of physical goods. One of the struggles of being a small business especially producing physical products in small volumes at early stages is the pricing is horrific. You can’t get pricing that makes your business competitive with more established firms. Dreamship helps shortcut much of this headache by giving creators access to production facilities and supply chains previously unimaginable. Essentially it lets the smaller upstart businesses get to market faster and compete in a global marketplace more efficiently. I got to know the founding team in the fall and am excited by their growth.


The value of management consulting delivered through software, playbooks and a network of experts.

I’ve spent a large chunk of the past few years in management consulting and know this space is ripe for disruption. Much of the industry is competing in a highly regulated space like audit, assurance, tax and other services that by definition have to follow standards like Generally Accepted Accounting Principles (GAAP). This means the services essentially become commodities with little differentiation across players. The last area for competition ends up being what can broadly be called “innovation” which includes M&A, spinoffs, spinouts, corporate innovation and anything else dealing with disruption and new business models. This is why we are seeing offerings like BCGDV, Capgemini Invent and similar value propositions coming from the big consulting firms. These engagements are solid seven to eight figures and only accessible by Fortune 500 size firms. This is where software comes in and can provide value for businesses who ordinarily couldn’t access this type of service. Laskie creates assessments that help firms leverage improvements in strategy, process and or delivery of service without incurring the expensive person-hours of traditional consultants. I’ve been fortunate to work with the Laskie team on a few of their initiatives.  


Founders: You’re owed $50K by the IRS. We’ll get it back for you in 20 minutes, no paperwork required. Free to qualify.

If you are old enough you may remember Matthew Lesko, the guy in the question mark suits who made commercials selling books that helped people apply to government programs like grants that would fund investment or education. There are billions of dollars available from governments and nonprofits that go unclaimed each year. These are particularly important for businesses to leverage given they are essentially free. The problem is accessing these funds usually takes complicated forms and outdated processes to access. Mainstreet modernizes this process to make it easier for founders and executives to get crucial capital to fund their businesses.


Use social posts as currency at select online stores.

We are roughly 15 years into social media and we are only starting to see the link between commerce and social networking. Influencer marketing is here to stay but to this point it has mostly been a one-way street. Influencer posts about the product after being paid by the brand for the exposure or gets a cut of the sales.  Swaypay flips the model on its head and lets people pay for their products by sharing the purchase to social media. While a few steps away from cash it is a relatively inexpensive way for a retailer to buy exposure without increasing their ad spend. I think swaypay will be acquired, or strongly imitated by a Shopify type company or similar eCommerce solution



Ideas, concepts, and blue oceans I am interested in. If you know of anyone working on something like this please let me know  

Intellectual supply chain

We are now nearing a year of nearly the entire business world working in a remote manner due to the covid-19 pandemic and remote work is here to stay. One of the unfortunately consequences of remote world is the inability to poke someone on the shoulder and as such a misalignment of operations. Sure you can call, text, slack, email, whatsapp etc but everyone has a different operating procedure so miscommunication can happen at scale in a remote environment. This brings an opportunity for what I see as project management 2.0 or a supply chain of business process work products. Asana, Trello et. al are great for one off task management but they really lack features for teams. Think of a client presentation that is due on the 30th of the month. That means a rough draft needs to be completed by say the 25th with 26-29 left aside for revisions. This requires rigorous alignment across the team’s remote processes. Everyone has a different work flow and work hours and newer tools will take these into account.

Calendar analytics

The calendar in its modern form has not changed much in the last 20+ years. Sure the desk calendar has been digitized but in 2020 it is essentially the same as it was in 1990. Calendars can run your personal and professional lives but mostly lack intelligence. As a calendar devotee I would love to get insights from how effective I am with my calendaring. What meetings run long? What are my most productive times? There are a myriad of insights waiting to be unearthed. A challenge here is logging each activity. Logging every minute of your day takes a ton of work which is why I see a larger opportunity with passive tracking efforts like RescueTime. Some might find that invasive but I propose it only is viewed as invasive it if doesn’t yield value. For example here is my year in review from RescueTime. Cool data but limited insights. I want an analytics system that improves how I operate. Microsoft is dipping a toe in the water with MyAnalytics and a startup called Reclaim has a similar value proposition.

Blindspot detector

One of the things I have noticed in corporate America is there is a tremendous instance of the prisoner’s dilemma; situations where coordination would be mutually beneficial but fails to happen. By that, I mean at nearly every company I have worked at or consulted with there is a layer of feedback that management does not give to workers and workers do not give to management due to misaligned incentives or fear of firing. I feel anonymity can be a powerful tool here but there needs to be some function that eliminates gossip or avoids retribution and only relevant feedback is produced. For example, take tools like StatusHero. Very powerful in theory but often folks are hesitant to put the most pertinent feedback into writing.  Software can be a great way to mitigate this problem. A few months ago I created a one pager of the offering and tried to build a service around it. I still believe this is a blue ocean.

Social delegation

For the last few months, I’ve been job searching and want to make it as easy as possible for friends and contacts to help me. That means more work on my end which I happy to take on but often there are barriers vis a vis my access to a friend’s network. For example, searching through a friend’s network is somewhat limited. I can’t only see a slice of who is connected to whom and asking a friend puts more work on their shoulder which is the opposite of the goal. I would like to see a way where can delegate our social networks to very close friends for discrete purposes. In this scenario I can more easily search through a friends network without making a huge ask on their part. In addition, this concept works while sharing or disseminating information. I love helping my friends, especially entrepreneurs. I would gladly give someone access to my social feeds to share messages that would benefit them. Of course this would only be for my inner VIP circle but I see an opportunity here. This is much easier than being constantly asked to share or RT things. I tweeted a little more about that here.

Email analytics

Similar to the issues with calendaring, the inbox remains mostly unchanged since the dawn of the internet. I’ve been a user of mailtester for a number of years but it doesn’t give me actionable ways to improve my inbox management. Here is my monthly email report from October 2020. I’d gladly pay for a service that improves my email workflows. Helps me spend less time here or learn where I am not responding appropriately or efficiently. There was a great startup called Conspire that published a monthly report for each of its users. You can see my report from a few years back here. They were acquired by FullContact but the product was deprecated.