All Startups need Capital – but what’s most Cost Effective?

Startup founders need capital – to pay salaries, to pay for marketing, to pay for everything that goes into building a business from the ground up. Bootstrappers may differ and say “I don’t need capital, I’m not raising” – but here (and I’m a 4x bootstrapper) I beg to differ. You are always using capital in a business – it just comes from different sources. There are tons of lists of capital sources out there, but here’s my attempt to provide some guidance on the pros and cons of different capital sources, along with ways to think about the cost of capital:

Customer Capital – I love this term. Customer Capital, aka revenue, is both the cheapest and highest impact form of capital. Since it’s coming from your customers, getting more of this capital is directly aligned with growing your business – success in sales begets more growth and cash flow which can be reinvested in the business.

Cost: This is the cheapest form of capital – from a “fundraising” perspective the cost of capital is actually negative, since free cash flow parked on your balance sheet can earn non-zero interest these days!

Pros/Cons: Not much to say here… there’s no better way to finance your company than through reinvesting sales! Bootstrappers beware – if you run a profitable firm, you’ll have to decide how much to reinvest versus how much to take home. I regret not reinvesting more in the past – when you’re paid many times revenue at acquisition, it’s more profitable to raise growth than to take excessive short term profits.

Sweat Equity – this is what bootstrappers think of when they say they don’t need to raise, but there’s an opportunity cost to your time dependent on your highest alternative salary. In my own case, I took a look at the years invested in HiddenLevers with a below opportunity-cost salary, and calculated that my sweat equity investment had actually been around 500k!

Cost: Calculate your after tax salary at the best job you could get right now, and compare that to your current startup salary. That delta is a simple approximation of the amount of capital cost you are borrowing from yourself via sweat equity. But what is the cost of that capital, the effective interest rate that you are paying? Well, since the alternative investment for this capital is likely other public market investments, we can pencil in around 10% here, since that’s what the S&P 500 has achieved over long timeframes since its inception.

Pros/Cons: Don’t be frightened by opportunity cost, as it’s still cheaper than outside investment – but use it as a yardstick to measure what a successful exit needs to be. Sweat equity may also be inadequate to start certain firms, and usually lead to a longer journey.

Revenue Based Financing + Venture Debt: Historically debt financing was not available to startups, as most are asset-light, meaning they don’t have anything to repossess if business goes south. And many a founder is familiar with using credit cards, home equity loans, and duct tape to hold their startup together. But newer sources have emerged, with revenue + invoice-based financing, working capital financing, and traditional debt becoming more common.

Cost: From an interest rate perspective, most of these will have a treasury spread of 500-1000bp – sorry for the finance gobbledygook – the rate will be 5-10% higher than the equivalent length US Treasury rate. That means a rate of 10-15% will be normal in this market!

Pros/Cons: A rate of 12 or 15% interest sounds crazy right? Well, if you’re growing your business at a fast rate like 40% per year, it might be totally acceptable, and cheaper than equity finance (because selling stock would be selling that 40%/yr growth to someone else). A major caveat – lenders will want to see some tenure (ie you’ve been around more than a few months) and positive unit economics, as per unit losses indicate that they may never get their money back! But that’s good discipline, we are no longer in a free money world, and all startups should be aiming for positive unit economics.

Friends + Family: The age-old equity investment!

Cost: Many founders now use standardized SAFEs or convertible notes for these rounds, but you may have more control over valuation cap and other terms, and generally won’t need to give up a board seat or other control. In terms of cost, see the VC section below, it’s higher than it seems at first glance!

Pros/Cons: Don’t mix work + family if you can avoid it! Think of it as diversification – if you tie work and family together with your startup, you’re putting it all on the line in one big bet. And this isn’t a source available to founders without some degree of affluence in their circles.

Angel Investors / Venture Capital / Private Equity: Ahh, the professional investors. I empathize with them, it’s not an easy job, particularly for early stage investors who are really investing in founders (as people) more than anything else. Many startups no longer need substantial capital to get started, but those attempting to conquer b2c or large-scale b2b verticals have substantial marketing needs.

Cost: Equity-based may be necessary for many founders, but it’s something of a necessary evil. If you fail, it’s all worthless anyway, so we don’t need to worry about that case. But if you succeed, and you get to the exit, you’ll realize just how much you paid for those first capital investments. If your startup manages a CAGR of 60%, that means that the cost of equity financing was at 60% interest, compounding annually!

Pros/Cons: I’ll say it again – there’s no more expensive source of capital than early stage professional investors. They are taking tremendous risks, and will ask tremendous compensation in return. But for the successful founder looking back, it may feel as if they’ve been eaten by a loan shark. What’s the old Kanye line? “Win the Super Bowl, drive off in a Hyundai…” For those playing in narrower markets (which are a great place to start), using any other capital source may be a good place to start. By maintaining a focus on unit economics, founders may be able to get to positive free cash flow, thereby unlocking Customer Capital on the road to success.

Successful Exits: Real, Fake, and How to tell the Difference

For those of us in the startup world, the term exit has a specific meaning. It’s the endpoint of a founder’s involvement with a startup. A successful exit means that the founder made a bunch of money right? The old adage on startup exits used to be that exits were measured this way:

Small: You made enough to change you car
Medium: You made enough to change your house
Large: You made enough to change your life

In public, we see exits measured by total deal value, and we celebrate the unicorns, and the 9-figure exits – but how often are we able to see what really happened from a founder perspective? Actual founder outcomes are important to understand for those in this business – and it’s important to understand opportunity cost and how to calculate Return on Investment for a founder. Here’s a rundown on “fake” exits, secretly unsuccessful exits, and a take on how to measure a founder’s actual ROI in an exit.

Fake Exits

1. Private Equity majority ownership stakes: You see the press release, the shining coverage – xyz startup sells for $300 million, or $1.2 billion! Dig deeper, and it turns out that a PE firm has purchased majority ownership from the VCs backing a startup. While founders may receive some cash liquidity, they have to stay on to deliver the next phase of growth. Founders “exiting” in this way in 2021 may find that their stake is now worth much less than the announcement price tag, as late-stage startup valuations have shrunk dramatically.

2. Stock acquisition by a larger private company: everyone gets stock in the rocket ship right? I founded a company in 1999 that was acquired by a pre-IPO Intralinks for $1.2M on paper in 2000 – my shares were worth $350 after the crash (I was 22 and it was a great education). This kind of exit could go really well too – but it’s not technically an exit, as you are just trading one illiquid asset for another, and you must keep up the fight until a future exit event.

3. Down Exit (below VC preference): When VCs and other early investors invest in your company, they often buy preferred shares, which come with a liquidation preference. If the company is acquired for less than this valuation, then the investors receive everything. Companies that raised at extremely high valuations in 2021 may find themselves in this situation. Consider a company that raises $300M on a 1.2B valuation in 2021, and then falls 80% in value in 2022 (in line with its public saas peers). If the company is forced to exit at the lower valuation, founders could end up with nothing despite having built a one-time unicorn!

This has happened before.

How to Calculate Founder ROI

Let’s say you get past all the traps, and you’re on your way to a successful exit. What was the return on investment of all the blood, sweat, and tears in the end?

Consider my situation. I was saving $150k per year (working FT + fractionally) prior to starting HiddenLevers. It took 3.5 years for my income from the business to equal this opportunity cost. It took almost a decade to build HL and sell from there, a time in which the S&P 500 roughly tripled in value. If I had kept working corporate jobs, I would have invested 525k, and that might have tripled to around $1.6M by the time of the HL exit. So I can compare that amount against my exit as one reference point – if I hadn’t exceeded that amount, I would have been better off keeping my day job! [1]

You can calculate your rate of return by dividing total exit by the initial sweat equity investment amount (in this case 525k), and then annualizing the result. If it’s greater than 10% you beat the long term performance of the equity markets.

It’s also worth noting that had I kept my day job, I’m sure that my career would have advanced, further increasing my opportunity cost. Now, none of this matters if you weren’t saving a dime to begin with, or if your quality of life doesn’t suffer as a result of starting a company. But most founders have other options, so it’s worth making the comparison to understand whether the numbers add up. And of course, this also provides insight into another thing – just how much you value being able to leave the grind and build something for yourself!

[1] We use net savings and not top line income, because we need to know how much capital you would have been able to invest in the alternate case, where you never left your day job. Net savings is a reasonable approximation of that – but if you’re the sort of person whose lifestyle expands to absorb additional income, then a comparison of after-tax salaries in both cases might be more relevant.

[2] To really calculate this accurately, you could create a spreadsheet that calculates opportunity cost year by year, but here I’ve just used rough averages to illustrate the point.

P.S. If you got this far – one way I got to my exit was by running super efficiently, and I’m proud of HiddenLevers’ 53% EBITDA margin at exit. Fractional developers helped me to get to that level of profitability – see how I can help you do the same via

Bootstrapping vs VC – a Founder’s Comparison

How does a bootstrapped exit compare to a VC exit, from a founder’s perspective?

TL;DR A VC-backed company will have to exit for 4-10x the valuation of a bootstrapped company, if the founders are to have an equivalent payout.

The above infographic (click to see the full version) does an excellent job illustrating the general stages of the startup company life cycle, except that most end in failure or acquisition rather than IPO. The percentages on the original graphic are dated and I’ve updated them above. The general point remains – each capital raise reduces founder equity in return for powering future growth. But the actual math matters – let’s take a look at some sharper numbers:

  • A typical VC-backed startup goes through four rounds prior to exit, where founders’ equity is reduced by 15, 25, 25, and 25%, with another 5 points lost to the options pool shuffle, advisors, board members, and other hangers-on. The four rounds are the seed round, Series A, B, and C.
  • The options pool shuffle is a clever trick VCs employ to capture a bit more equity. Advisors and board members often command 0.5 to 1% of the company each as well.
  • The compound impact of this at exit: founders’ + employees’ equity at exit totals 30% (a range of 20-40%). If we assume 2% in exit transaction fees and 8% fully diluted to employees, that’s 20% to the founders at exit.
  • Using the same assumptions, a 100% bootstrapped company has only the final 10% in exit transaction fees and employee compensation, leaving 90% to the founders.
  • The math above is daunting: 90% vs 20%! This tells us that founders should go the traditional VC route if they believe that it will enable them to exit at least 4-5x larger than the size of a bootstrapped exit. I’ve validated these basic numbers in conversations with a number of founders, and while the particulars will vary, the general guidance holds. Many founders give up too much, and end up as low as 5% at exit.
  • This assumes that your company can get somewhere without funding, which may not be realistic.
  • Bootstrappers trade time for money to an extent, if growth is ever constrained by lack of funding.
  • When choosing whether (or how much) to raise, consider your total addressable market. If you’re in a profitable niche, bootstrapping may be optimal. If your TAM is greater than $10B, go raise money.
  • There’s an intermediate option – raise, but raise wisely. Bootstrap your MVP, raise after you’ve got something repeatable, and raise all you can that one time. If (and when) I do it again, I’ll strongly consider this option.

Here’s a sample of Real-Life Exits:

  • GrubHub founders Mike Evans and Matt Maloney each held about 2.6% of GRUB at IPO – this degree of dilution is unfortunately common.
  • At the other extreme, David Barrett owned 47.7% of Expensify at IPO – proving that with judicious use of capital, dilution doesn’t have to be extreme.
  • The founders of Toast (TOST) collectively owned about 17% of the company at IPO. This was worth $5.1B at IPO, but has fallen 70% since, with share lockups preventing a true exit.
  • Mailchimp was the king of bootstrapped startups, going from 0 to $12.3B at acquisition, and succeeding in a space while competing against startups equipped with $100M+ in funding. Had the Mailchimp founders’ ownership been similar to Toast, Mailchimp would have had to sell for $74B to net the same founder outcome!
  • Private exit data is harder to come by, but Riskalyze saw the founder and CEO holding roughly 16% at exit to private equity (this was not a complete exit, as the PE firm bought a majority stake but kept the team onboard).

Why HiddenLevers Never Raised Capital

When I started HiddenLevers and roped in my cofounder Raj in late 2009, we talked about what success looked like. We thought success would be running the company for a year and selling it for … two million. We thought we could demo our cool new portfolio stress testing technology to major brokerages and just have one of them snap it up! Naive – but also a comical underestimate of the value we could create.

It took us about a year to reach a semblance of product market fit, which occurred when we found the RIA space – independent financial advisors understood the value of using HiddenLevers for their end clients. Over the course of 2010 we had been researching addressable markets, and one thing I’m proud of is the quality of the TAM modeling we did at that time. A decade later it was still essentially accurate – we were in a highly profitable niche space, with several hundred million in total addressable market for the financial advisory space. Here’s the spreadsheet from September 2010 – row 12 is where the business ended up thriving.

We looked at that TAM and worked top down and bottom up – from the bottoms-up perspective, we set a make or break goal of 100 clients by July 4th 2011 or we would fail fast and shut down. From the top down perspective, I calculated – what kind of business value results from capturing one percent of this audience?

Looking at the business from both perspectives, a few things became clear:

  1. We were able to use trade shows, email marketing, adwords, and press coverage to grow profitably, and it wasn’t clear that investor capital solved a problem – we had free cash flow to reinvest.
  2. If we did raise capital, the scale of our addressable market damaged our chances of a successful founder exit – diluting your stake works if it’s in pursuit of a massive market, but poorly in a niche.
  3. Successful expansion outside our niche might require capital, but growth within it did not.

In 2020 we reached an inflection point – to sustain our growth, perhaps it was time to finally raise a round so that we could expand upmarket, build out an enterprise sales team, etc? It was this inflection point that caused us to reach out to the M+A market – the early growth phase of the company was complete, and we felt that it was better to join forces with a more mature organization than to try to build that organization ourselves.

For a business like HiddenLevers, bootstrapping fit perfectly. The math I outlined up top held up well, and it’s quite possible that taking capital would have actually hurt our exit outcome. But if I ever try to build something to conquer a big market (over $10B TAM), I’ll do it the “normal” way – with investors.

Business Ideas VII: GuideMe

Idea: GuideMe – an automated guidance counselor that helps students make better college and career choices

MVP: Too many students in the US leave college with too much debt and no realistic career path – in part because guidance counseling is a luxury at many American high schools. GuideMe will help fill this void, using students’ interests and strengths to show each student the college or vocational programs that will help them achieve their goals. GuideMe will also help students evaluate admissions offers to determine the best choice in terms of career ROI, taking into account both costs and future income.

Market: US high schools average one guidance counselor per 500 students, leaving most students with no career guidance except what’s available via friends, family, and the internet. In this vacuum there’s a tremendous opportunity to help students and families make better choices, with better careers and less debt the end results.

From a business model perspective, students and high schools have limited resources, but employers have a substantial recruiting need, and a successful app could funnel qualified candidates into positions at a far lower cost than traditional means of recruiting. There are over 150M working Americans, 100M of whom lack a college degree. The vast majority of that 100M employees might benefit from vocational training and placement services – almost 50% of employees change jobs annually. If the value of placing an employee is conservatively estimated at $1000 (versus the 20-25% of salary typically paid in white-collar recruitment), this leads to a total addressable market as large as $50B. [1]

Idea Score (0-10 scale): 8 points

Feasibility of MVP / Market Entry (out of 2): 2

The GuideMe MVP would leverage data on salaries and tuition published by college programs in order to determine career ROI, adjusting each career path for projected future changes. Much of this data is either publicly available or can be licensed, but it may need to be refined newer or non-traditional careers.

GuideMe would then determine the highest ROI programs for a student, based on their GPA, test scores, and interests. Virtually all of the data needed for the MVP is publicly available, though career ROI estimation algorithms vary – given my experience building HiddenLevers, this should be a competitive advantage.

Revenue Market Size (out of 4): 4

As noted above, the total market opportunity in the HR recruitment space, taking into account only the under-served vocational market, is conservatively estimated at $50B  per year.

GuideMe’s principal issue is that the initial platform rollout is devoid of any revenue generation plan – users in the cost-conscious student market are unlikely to adopt a paid guidance product. GuideMe instead intends to roll out a full-featured free product, while developing a placement product for employers requiring specific skillsets. GuideMe will be well positioned to match capable students with employers, enabling higher volume placement at a lower cost to businesses.

The challenge in building a two-sided marketplace style product is well known, but the returns to success can also be extraordinary.

Difficulty, Barriers to Entry, and Competition  (out of 2): 1

Many sites and apps exist to provide guidance in aspects of the college decision process, but none  provide comprehensive career guidance, and none utilize the concept of career ROI.

Existing competitors like MyKlovr are attempting to solve aspects of this problem, but appear to be focused on paid software approaches, which will limit growth potential. There is substantial risk involved in building  a free guidance product, and then working to link it to employment placement, but this approach is likely to capture the largest number of users in a space where massive scale is possible.

Riding Hype or a Trend (out of 2): 1

At present there seems to be little focus on this market – but if scale can be achieved among the 20M students in US high schools, then building a funnel to employers should become relatively straightforward. Very little has been done to improve the functioning of the middle of the US job market in particular – the rewards are too small for traditional HR firms to work hard at placing a plumber. Automation is the key to unlocking the scale potential in this market – and early career guidance is the key to bringing large numbers of candidates to market.


[1] Public companies like Randstad, Adecco, Robert Half, and Manpower show that valuations in the $5-10B range are possible in this sector.

Business Ideas VI: Run My House

Idea: Run My House – manage all your household services from a single app

MVP: Running your own house sucks – even if you outsource tasks like yard service, gutter cleaning, pest control, and cleaning, it’s still a challenge to deal with numerous service providers by inefficient means like phone calls. What if you had an app that enabled you to simply check off the service subscriptions you desire, and to take pictures to show problems needing resolution? Even when homeowners work with their existing service providers, there are major communication inefficiencies – not to mention the difficulty in acquiring good providers in the first place!

The difficulty with an MVP in the home services market is chiefly a business problem – a substantial percentage of home service work is performed in the informal economy, and as a result it’s highly fragmented. As a result this business is best attacked in a single test market to start, as providers need to be secured across all major services in order for homeowners to realize value in the service.

Market: The combined household market for home cleaning, yard service, pest control, gutter cleaning, and related scheduled services exceeds $100 billion per year, and including non-scheduled maintenance the total market may exceed $500 Billion annually. This market is currently incredibly fragmented, in no small part because there are limited economies of scale in providing most of these services.

Unfortunately for the consumer, this leads to a terrible experience. If Run My House can capture a 10% fee for delivering volume to providers, while keeping the cost to consumers static, it should be possible to capture meaningful market share. With a total addressable market greater than $10B, there is true unicorn scale possible in this market.

Idea Score (0-10 scale): 7.5 points

Feasibility of MVP / Market Entry: 0.5

Building an MVP for RunMyHouse could be daunting, given the number of service providers that must be secured before the service becomes compelling. This sort of “full-stack” startup, providing a complete service rather than just software, has larger potential but also substantially greater risk and capital requirements. Typically it makes sense to attack individual metro areas individually, starting with a beta market and working through challenges there first.

A simpler alternate MVP might simply help homeowners organize communication with existing vendors – perhaps by providing the software for free, with vendors selling their services via the app. This Zenefits-style approach (the give-away-the-software part, not the HR disaster) could enable rapid expansion at lower cost.

Revenue Market Size: 4 (out of 4)

As noted above, the total market opportunity in the residential space is several hundred billion per year – a 10% take rate implies a true addressable market size of 20B+. Numerous public players in the home services and home sales space (ANGI, Z) point to the possibility of a unicorn valuation for a successful player.

Difficulty, Barriers to Entry, and Competition  (out of 2): 1

A large scale b2c rollout of this sort would likely require substantial funding. HomeJoy was a substantial failure in this space, showing that giving away services at negative margins can take even well funded startups down. Handy, its largest competitor, has since worked hard to get to profitability, underscoring the risks of the home services market.

Taking a software-only approach could lower the risk of rollout, but substantial marketing spending would still be required to get customers and providers onboard.

Riding Hype or a Trend? 2

Bringing fragmented, illiquid, hundred-billion dollar markets online has been one of the key success stories of the last 20 years of the internet. Home services has been among the final frontiers because of its deep fragmentation, but Uber and ride-sharing proved that change will come to even the most glacial industries.

Business Ideas V: BestUse

Idea: BestUse – analyze real estate through the lens of local zoning and code to determine best use, and identify underused properties

MVP: The process of identifying promising opportunities in real estate is largely a manual one today. Real estate investors and agents scour listings and property records to determine where opportunities to convert an old office into multifamily housing might exist, for example. BestUse would automate this process by using machine learning to compare zoning laws and potential uses to identify underutilized properties. A minimum viable product would involve targeting a particular metro area to analyze local zoning and building rules there in detail.

Market: BestUse has a likely path to market very similar to HiddenLevers (my current concern). The advantage of selling high value software in a niche market is that initial clients can be acquired very quickly after alpha release – the moment HiddenLevers portfolio stress testing worked in a minimal way for a professional audience, client acquisition amongst investment advisors began. With BestUse, real estate investors might quickly embrace a technology that enables them to identify “diamonds-in-the-rough”, properties currently languishing in a sub-optimal use.

The downside with this approach – the total addressable market tends to be limited: if real estate investors are willing to spend four to five figures per year for this capability, the total addressable market might be in the billion dollar range – enough to build a viable business, but not enough for a highly scalable growth path.

Idea Score (0-10 scale, up to 2 points per question): 6 points

Feasibility of MVP / Market Entry: 2

An MVP for BestUse would require a non-trivial initial effort to acquire needed real estate data and to plug in the appropriate analytics on local real estate codes. Actual market entry would likely follow a pattern similar to that for other niche analytics products – get in the hands of paying beta customers and iterate. This is a proven model with much lower risk than launching b2c oriented products.

Revenue Market Size or Eyeballs: 1

If the market is confined to analytics tools used by the commercial real estate industry, then the total addressable market is likely to be subscale (no unicorns here). A high margin $10M revenue business is possible, but getting past this to the next level is a key concern. Since the same sort of analytics is used in commercial real estate appraisal (an $8 billion market), adding this and related capabilities might push the scale a bit – but it’s not clear how to get to a $10B addressable market.

In a Growing Market? 0.5

The real industry is very mature, with growth rates unlikely to exceed the overall economy.

Difficulty, Barriers to Entry, and Competition 1.5

BestUse requires a combination of knowledge of real estate investing with technical modeling capabilities, providing a modest barrier to entry. The need to analyze zoning rules further raises the bar here.

Startups have started to appear in this space – Skyline is using similar analytics to partner invest in properties, an approach which might lead to greater overall market potential. Bowery Valuation is focused on automating real estate appraisals, a naturally related market.

Riding Hype or a Trend? 1

Applying advanced analytics and machine learning to any niche generates interest at the moment – but this is not a particularly innovative or new use case.

Business Ideas III: HalfTimer

Idea: HalfTimer – Link employed developers with spare capacity to half-time positions

The economy is going full steam. The number of job openings is at an all time high [1]. Technology positions are particularly in demand, with hundreds of thousands of developer positions unfilled nationwide.

MVP: places developers interested in long-term part time employment with companies looking for experienced development talent. We have found that experienced developers are willing to lower their hourly rates by up to 40% in order to secure a long term contract that is in addition to their full time job. This differential enables savings for companies that work with HalfTimer – a substantial competitive advantage in the staffing business. The initial MVP need not involve more than outreach to employers and developers via LinkedIn, to staff the first several candidates and prove the model.

Market: 5M full time technology professionals builds on a concept successfully used by my other ventures to tap an underutilized resource: experienced, full-time employed developers. Many developers, particularly at large corporations, are not fully utilized whether in terms of mental capacity or even time (this documentary details the situation at length). There are almost 5m individuals employed in development-related positions in the US today – if even 10% have excess capacity, this represents a pool of 500,000 potential resources.

Scoring (0-10 scale, up to 2 points per question): 6 points

1. Feasibility of MVP / Market Entry: 1.5 points

The HalfTimer concept exploits an inefficiency: most employers historically won’t buy limited hours for professional work. On the developer side, developers looking for additional freelance work find it difficult to consistently find small projects that fit around their day jobs. HalfTimer attempts to solve this problem, and market entry is straightforward as this is just a new spin on existing staffing concepts.

2. Revenue Market Size or Eyeballs: 1.5 points

500,000 potential HalfTimers, with net revenue per resource at $15,000 = $7.5B/yr total addressable market. Put another way, staffing ~100 HalfTimers would generate 1.5M in net revenue (against roughly $6.5M in gross revenue), enough to run a profitable small startup. The crucial question: cost of acquisition of both employers and employees.

3. In a Growing Market? 2 points

The technology employment market continues rapid growth, and the core constraint remains supply – which is precisely the problem HalfTimer seems to resolve.

4. Difficulty, Barriers to Entry, and Competition: 1 point

Many existing players in the staffing space could potentially attack this idea, and technically there are no real barriers to entry. Gigster,, TopTal, and FlexTeam are startups attempting to ease companies’ ability to find freelance talent – these are similar but not identical to the HalfTimer concept (startup competition bolsters the strength of the idea, as it confirms an idea is worth exploring).

5. Riding Hype or a Trend? 0 points

The gig economy has grown substantially, and HalfTimer represents an evolution halfway between freelance and traditional full time employment. But it’s not clear that concepts in this space have much mind-share at the moment.

[1] The JOLTS survey shows the number of openings to be at an all time high, even when compared to 2000 and 2007 on a relative basis.

Note: I changed the first scoring question to address feasibility rather than whether the idea is “transformative”, which seems to be an imprecise concept at best.

Business Ideas I: Juggler, Never Let A Message Drop

Over the years I have kept a running spreadsheet of business ideas – my current business, HiddenLevers, was once a denizen of the same spreadsheet. But ideas have expiration dates [1], and my idea list has grown while my available time has shrunk. Over the next few months I will be sharing my ideas – I’d love to hear feedback and to inspire others to take the next step or gain inspiration. To provide structure, for each idea I’ll share my thoughts on what I thought the MVP might be, and a scoring of the idea using my own 10 point scale. Here goes!

Idea: Juggler – Never Let a Message Drop

Juggler would watch your firm’s emails, LinkedIn, and other messaging platforms to ensure that every inbound request is tracked and gets a response. The challenge today is that inbound business communication arrives across channels, and often comes in to many different personnel at your firm. Using AI, Juggler would determine which messages actually require response, and monitor these across all firm users, alerting managing when prospects and clients are awaiting response.

There are a ton of AI-based email solutions and also support email solutions from firms like Zendesk – but none of these seem to focus on this specific use case – firm-wide monitoring and taking a global look at all communications to a particular client.


The MVP is simple – do the machine learning work to simply determine whether a particular email requires response. Emails asking questions clearly come to mind – but taking a true machine-learning approach, can we approach 99% accuracy here? This can then be married to a simple UI showing individuals (not messages) requiring attention – this sort of dashboard data could ideally then be integrated into Salesforce or other CRM platforms.

Scoring (0-10 scale): 6 points

1. Is it Transformative? 1 point

This is a fairly standard use of machine learning in 2018 – but the accuracy level required to make this viable is not. Also, many businesses still don’t take real advantage of CRM systems, and this idea automates some of the key value concepts from CRM for a small business (ie don’t let any leads slip through the cracks – I’m looking at you, contractors).

2. Revenue Market Size or Eyeballs: 1 point

This is a broad market – virtually every business could use this capability, so volume pricing of even a few dollars a month in a SaaS solution could scale quickly. Presuming that this capability is worth $5/user/month – the US market alone is greater than a billion per year.

3. In a Growing Market? 1 point

While email utilization is stable, multi-channel communication is growing – think chat, social media, VOIP (phone) – in theory the same approach could be applied to all of these.

4. Difficulty, Barriers to Entry, and Competition: 1 point

It may prove difficult to achieve the level of accuracy with machine-learning to inspire user confidence. If businesses suspect that even a few important messages might be slipping through, they will lose confidence and not use the product. Ideally the system ought to learn based on each user and firm’s data – posing a bit more complexity.

5. Riding Hype or a Trend? 2 points

AI and machine-learning are arguably THE trend of the moment, and while arguable overhyped – the Juggler idea definitely is riding this trend.


[1] James Watt’s steam engine was an excellent invention, and applying it to pumping water out of mines an excellent business idea – for the 1770s. The concept of hailing a car via smartphone was likewise a great idea – in 2009. It’s also possible to be too early – Yahoo Briefcase shutdown the same year DropBox was founded (although the latter was also a vastly superior implementation).


P.S. Investors out there, feel free to reach out if any ideas in this series are of interest – while my core business continues to grow rapidly, I’m open to discussions on how to seed fund and launch against many of these ideas.