Perils of a Rich Valuation

The entrepreneur gushed “We just closed a $2.5 million Series A on an $8 million pre-money valuation.”

My response: “Great news – now that you’re a couple months past close, what’s the probability estimate of hitting the 1st year revenue target you set for the VC’s?”

The smile quickly vanished as the entrepreneur acknowledged it was far from being a lock to hit the target. Both the risks and attendant pressures were already starting to hit home.

Valuation optimism can be masked with insufficient data

Unfortunately, this is a much too common scenario as founder drive to minimize personal equity dilution by grabbing the fattest valuation possible seems to override their judgment on what happens post deal.

Typically the culprit is too little thought given to the underlying assumptions behind a detailed bottoms up financial model. Proper models take into account factors like average deal size, sales process steps and time to close, productive lead sources beyond executive team personal relationships and diminished close rates of non founder sales reps. [See my post: Leading Sales as a Startup CEO].

The worst offenders set their valuation target first and then back into a set of projections that align revenues with the valuation goal as they scurry about for data points supporting their wished for revenue trajectory.

While VC’s will certainly review assumptions behind revenue as part of their due diligence, entrepreneurs will get some leeway if the product offering is distinctly different with what’s already in the marketplace (thereby lacking trend comparison with similarly situated companies) and you’ve already racked up a few sales to your credit.

Overly optimistic projections come with consequences

The path to judgment day starts with board meetings in which the new institutional investor board members are now brought up to speed with the insider’s view of your progress against the expected revenue targets that were in the deal.

If you’re absolutely confident you’re right on path to meet or exceed the targets then you’re golden.

But if you’re starting to break out in a cold sweat soon after the deal closes, then you’ve got the hard choice of perpetuating expectations you may not have confidence in or going about the delicate process of resetting expectations.

Perpetuating the improbable is a gamble that ever optimistic entrepreneurs take, believing somehow, someway they will find a solution over time.

However, as projections don’t get fulfilled, that factor alone becomes the biggest reason entrepreneurs get pushed out of the CEO role in favor of someone who has a proven track record of “meeting the numbers.”

And that equity stake the founder was concerned about? When projections get missed and Series A funding dries up while there is still a substantial burn rate – you then have the classic down round scenario where in order to keep the company alive with a new financing, founder shares can get crammed down to a pitiful percentage of ownership compared to their post series A stake.

De-risk with detailed assumptions behind revenue components

You can mitigate risk by building a detailed model for how revenue projections are derived.

List assumptions behind each component of a revenue formula so there is complete transparency and no “black box” – even tilting assumptions towards most realistic, if not outright conservative achievement at critical components of the revenue formula.

The best entrepreneurs don’t settle on just a high level view of 2-3 revenue component steps to come up with a formula. Instead they tear apart every step in the customer acquisition process to find patterns which can be reasonably tracked (with a minimum of admin burden) that help point to predicting success at that particular step in the sales process, and in the aggregate – timing of future revenue flows.

Since early stage companies typically won’t have a large enough team for a professional CFO on staff to build such a model, they can fill the expertise gap with an “Interim CFO” who has the background and strategic perspective to dive in and gather input from multiple team members to guide a true bottoms up model with detailed, defined assumptions.

The best interim CFOs divide their time among a cadre of early stage companies and often have the pattern recognition of having been through this exercise across many similarly situated companies. This helps not just in developing the model but with an ongoing retainer relationship will help their client tweak the model as more data comes in and analytics for management and board are refined.

While it’s best to avoid optimistic projections pre-deal, the earlier that investor expectations get reset to the proper level the more likely you are to retain your credibility as a leader.

So don’t wait for your next round to beef up the visibility and accuracy of your forecast. When you’re depending on other people’s money – than your success, and that of your company, may end up riding on how well you can predict the future with a financial model that you actually deliver on.

[Related post: Embrace Public Company Readiness in Scaling a Private Company]


Tribute to Chris Spagnola

My wife’s Dad passed on May 26th, a few months shy of his 99th birthday.

A long life, well lived. In every respect, Chrisopher Spagnola was the epitome of our “Greatest Generation.”

Like others born into large immigrant families Upstate in the early 1900s, his growing up in the depression era faced hardship that shaped life perspective and was then reset by the enormity and calamity of World War II.

Volunteering to serve in the Army Air Corps, Chris quickly advanced to flight school where he was commissioned an officer and at 23 years old, commanded a nine man crew as he piloted a B-24 bomber in the European theater.

He flew combat missions until Germany’s surrender and his 36 combat missions exceeded the 32 mission requirement making him eligible to return to the U.S. for non combat duty. To put this in context consider that by his volunteering to fly more combat missions, he was aware that within the 8th Air Force Bomb Group he was part of there was about a 25% fatality rate on the bomber missions being flown in that time period.

Awarded the Distinguished Flying Cross and seven other medals recognizing his extraordinary valor and combat record, Chris continued his military service in the Air Force Reserves, retiring as Lt. Colonel in 1972.

At the close of WWII he returned to Auburn NY where he married his hometown sweetheart Clementine “Dutch” Boglione for a union lasting 62 years until her passing in 2010.
In 1946 he obtained his commercial pilot’s license but declined an offer to fly for American Airlines to instead begin building the Auburn Foundry company – which he ran as co-owner and President until his retirement in 2006. The business remains one of Upstate’s last independent foundries – a testament to the strong foundation and team he built.

Putting others ahead of self

Given his war record, extended military service and success as a local businessman, accolades from those exploits alone would be a full life for many. But for Chris, life wasn’t about achievement as much as it was making a difference for others in ways that might not garner recognition, but truly had an impact.
He volunteered across a whole range of organizations like Knights of Columbus, Kiwanis, his local golf club and others. Chris successfully led an effort to engage an entire neighborhood of lakeside residents to pool their resources for creating a paved county road and bring in sewer and water to the area – something that would not have happened without a collective citizen coalition such as he put together.

Beyond being active as a leader who got things done, it was Chris’s persona of easy going, rock solid integrity and always sensitive to the feelings and situation of others that endeared him to all he met.

He lived a Christian life doing things that made a difference in the lives of others, including for disadvantaged people on the margins of society. Appreciated by his community, he more than deserved the reputation of being a soft spoken, low-key hero.

Role model for the next generations

Chris was a hero to me and someone I appreciated from the first day we met 40 years ago.

As I matured, I also grew in my understanding of how the role model he was influenced his daughter Krista in ways that both attracted me to her and set the foundation for own marriage.
So as our children were in elementary school in California, and we thought hard about our priorities in their upbringing, uprooting from Silicon Valley in 1999 to come home was very much based in having our kids take advantage of the special grandparents they had.

These last 17 years with him have been more than special. As saddened as we are to no longer have him with us, we’ll forever cherish both the memories of our time together and how lucky we were to have him be such an influence in shaping our lives.

The example he set in living a truly full and impactful life inspires me, our family and the lives of others he touched. His legacy lives on and will never be forgotten.

“Those we love can never be more than a thought apart, for as long as there is memory, they’ll live on in the heart.”


Discovering Self Inside a Super Maximum Security Prison

Pelican Bay Supermax Prison. I’m locking eyes with Gary, separated by a perforated metal screen as zero physical contact is permitted with residents of the Secure Housing Unit (SHU), the prison’s solitary confinement facility.

While I’m aware Gary has been “inside” for more than 15 years, I’ve no inclination to ask about his reasons for being here.

Instead, we’re focused on an exchange guided by Defy Ventures CEO Catherine Hoke as I’m part of a team of 20 volunteers who are all facing individual SHU residents and now engaged in a series of interactions advancing each resident’s ambition to change their life by taking advantage of Defy’s highly refined program featuring guided personal development with many check points for accountability along the way.

The warden tells us it is the first time a group exercise has ever been done at Pelican Bay SHU, as no organization has ever ventured in with a track record to suggest having an impact on this segment of residents who are as isolated from society as you could possibly find.

Defy Ventures is a seven year old non-profit committed to reducing America’s recidivism rate. More than two-thirds of those released from prison, returned to incarceration within 5 years.

This mind blowing rate of returning people to prison is just one of the forces propelling the U.S. to hold 25% of the total prison population of the planet, even though we have less than 5% of the global population.

While other forces like lack of opportunity in disadvantaged areas, broken families, substance abuse, underperforming public education, electoral politics and inherent bias in the criminal justice system all have layers of contributing factors that go beyond the scope of this post, no one would disagree that a primary goal of our prison system should be to rehabilitate the incarcerated so those released can be productive in society and break the cycle of criminal behavior that too often continues into succeeding generations.

Not surprisingly, as employers are reticent to hire released felons, a parolees’ lack of opportunity to progress in society erodes hope and triggers gravitational pull back to the relationships and environment, which too often leads to a subsequent criminal act.

Defy’s approach to addressing this seemingly unsolvable problem is to help both prison inmates and recently paroled join on a committed path as Entrepreneurs-In-Training (EITs) – enabled by a combination of tightly structured self development and hands on help from a cast of highly accomplished volunteers.

The results of this program are nothing short of astounding. Of the 2,000 Defy graduates, 166 businesses have been created, spawning 350 new jobs for people with criminal histories.

Defy has had only 3.2% of their graduates return to prison. When you consider the cost of incarceration in California is $70,202 per year per inmate and an investment in an in-prison Defy EIT is $500, that results in a 294x SROI for California’s taxpayers.

But the win is far more than dollars saved as the real victory is putting individual lives on a productive path, breaking a cycle of returning to criminal behavior and bringing positive effect on lives surrounding the EIT like their family, friends and others seeking to break away from criminal behavior.

Everyone Invited, Only the Committed Advance

Being an entrepreneur is an alluring path for many, especially people with a limited range of options available to them. But only the committed will thrive as the failure rate for small business is often cited at 80% within the first five years.

Defy has evolved their entrepreneur development program so that it combines online and in-person exercises requiring an EIT’s sustained commitment to advance towards graduation.

Parolees access Defy’s online learning modules over the web and because, inside prison this is typically not an option, Defy’s video based learning can be accessed on the prison’s TV network.

At each phase of development, EITs are given assessment exercises that are tracked for completion through Defy’s Learning Management System.

In both “inside” programs and those on parole, EITs form support groups where they are helping each other stay on track, forming relationships with those who share a common ambition of finding success through entrepreneurship and strengthening commitment to avoid returning to a criminal life.

Mutual Respect Begins With Shared Understanding

As EITs progress in their development, they are offered opportunities to participate in high impact personal interactions with a very impressive group of experienced entrepreneurs, executives and investor volunteers.

Through a series of interactive exercises, volunteers and EITs come to know each other and learn about each other’s lives in ways that highlight their differences and similarities. In one exercise, separate lines of volunteers and EITs face each other, then step to a center line acknowledging how environment, family and impact of selected circumstances played out with either fortuitous or unfortunate outcomes now determining their status as an EIT or professional volunteer.

It is the similarities more so than the differences that are striking for me.

Like most volunteers, it is a huge “aha” moment to wrap my head around the realization that, with just a minor twist in my own life circumstances, it could easily have been me standing in the EIT line or see EITs with the clear potential to have ended up on the volunteer line as successful professionals.

That shared understanding of each other’s position begins the process of building mutual respect that in turn powers advancement of both EITs and volunteers in our respective journeys.

For in-prison events, volunteers provide coaching to EITs on topics that include articulating their personal elevator pitch, resume feedback, mentoring on the business idea the EIT is developing and participating in pitch competitions.

Volunteer support for those who are released include those activities as well as supporting and tracking an EIT’s progress and linking EITs to resources that can help their business succeed.

In all situations, EIT contact with volunteers follows a strict protocol managed by Defy in a way that preserves privacy and security considerations.

A Different Kind of Volunteer Impact

Since I was already deeply engaged in helping lots of first time entrepreneurs, the fit for me to check out Defy was pretty easy. While the audience was different than the startup world I am typically engaged in, the activities seemed right within my wheelhouse.

My expectation before volunteering was that my ability to have impact would be based on my knowledge, entrepreneurial experience and relationships I could bring to the program.

But beginning with my first event, the nature of my interactions with EITs were in such sharp contrast with the traditional world of helping startups I began to understand this was less about my professional qualifications than it was an opportunity to grow by being vulnerable and giving without expectation of return.

You see in the traditional startup-coaching scenario we don’t spend much time showing personal vulnerability. We go right to diving in with the help and expertise we think we’re there to give.

And even if we tell ourselves we have a “pay it forward” mindset, we know the startup world has so many interconnected relationships there are paths where our volunteer contributions may come back in some form of unexpected reciprocity – be it new deal flow, a helpful entrepreneur or investor contact, or referral to a highly valued source that can help us.

Defy Interactions Can Be Transformational

The Defy personal interactions are humbling in their effect of acknowledging vulnerability and rethinking about forces that led to how I arrived at the stage of my life where I can qualify as a Defy volunteer.

And when there is zero expectation of reciprocity, it forces the commitment choice on what my real reason for volunteering is – am I sincere enough in my values to walk the talk of pay it forward, or not?

Locking eyes with Gary and continuing our discussion through the perforated metal screen brought home that realization on how any impact I was having wasn’t about my professional experience, but instead my ability to show understanding, compassion and commitment to someone otherwise cut off from society.

I’m thinking that after our exercise concluded, Gary replayed the interaction in his mind as many times as I have. For different reasons, perhaps we both came away feeling we grew as a result.

So my own success measure for Defy volunteer participation is now flipped from where I was at the outset.

These powerful in-person interactions have done much to alter my personal outlook in a transformational way – something that I simply don’t get in the traditional role of mentoring startups headed by people that have already been dealt a pretty good hand.

But that benefit of a transformational outlook comes only as a result of participating with Defy in person.

It’s alluring enough to keep me coming back for more, and is probably the underlying force behind Defy’s high rate of returning volunteers – which is the only kind recidivism you really want to see!


Crossing Boundaries to Build Startup Community

A delegation of a dozen business and professional community leaders from Binghamton took a day out of their already busy schedules to travel to Syracuse. They toured assets in the Syracuse startup community, and interacted with local leaders to learn from their experiences in building startup community.

The delegation included people from Binghamton Chamber of Commerce, City government, Binghamton University and local business leaders. These people are committed leaders with a stake in growing Binghamton’s startup community. They understood the value of getting an inside look at steps a neighboring city went through to build momentum around creating companies and jobs in newer industries. These efforts are now attracting top talent to a revitalized downtown area, and certainly worth paying attention to.

Journeys begin with vision

CenterState CEO’s Rob Simpson welcomed the delegation and provided an overview of some initiatives that started a decade ago. This ingenuity included critical public private partnerships, which set the stage for today’s job creating thrust.

A tour of the Syracuse Technology Garden, undisputed hub of Syracuse’s tech community, featured a recap of programs and entrepreneur supporting activities. Rick Clonan presented, and had John Liddy, Founder and Director of the Syracuse Student Sandbox sharing insights on how the college student accelerator engaged local mentors that were critical to graduating students deciding to put their roots down in Syracuse instead of going elsewhere to start their first company.

The delegation toured the new Syracuse Marriott Downtown (a project CenterState CEO helped lead), and enjoyed a luncheon discussion with Marc Viggiano, a retired business executive who shared his personal experience on how becoming involved with the Seed Capital Fund of CNY, StartFast Venture Accelerator, Genius NY program and Upstate Venture Connect all lead to helping entrepreneurs start companies and create jobs.

Entrepreneurs revitalizing downtown

A tour of Syracuse CoWorks, a nationally prominent co-working/living space, provided an inspiring look at how downtown space can be configured to foster relationships that attracts both millennial entrepreneurs and residents. The “community” also serves as a base for StartFast Code – a coding academy that puts individuals on a career path as professional web developers or helping advance their existing businesses.

Final stop was SpinCar, graduate of StartFast 2013 cohort and now a blossoming company with 40+ employees headquartered in Syracuse. Co-founder Mike Quigley shared the SpinCar story, including how the community helped his team on the path to success. This included connections to key people and resources of which Mike says made all the difference in SpinCar getting to the right customer market, finding investors and talent.

We closed the day with an engaging discussion around elements of a strong startup community. This long-term outlook and willingness to cross geographic and institutional boundaries relies on people working in concert. The result is connecting entrepreneurs to the resources needed to grow companies and create high-paying jobs.

True leaders break new ground

Five or more years ago, we could not have seen a delegation from one of our Upstate cities traveling to another community to learn about building a startup ecosystem like this. Not only would best practices have been harder to identify, but the interest to travel and learn from others just wasn’t getting any traction.

Over the last year, I’ve spent a lot of time in Binghamton and I’m impressed with the seeds of change that have clearly been planted. There is no doubt that this group of leaders, who are crossing boundaries are leading the way in accelerating change. Working together, we’ll have a meaningful impact in growing companies and creating jobs in Binghamton’s future economy.


Road Trip: Spending time with those we love


I just completed a drive home to Little Falls, New York originating from the San Francisco Bay Area.

With a few zigs and zags, it was about 3300 miles over 8 days.

This was my 9th cross country road trip, but the first with my son Jared since 1999 when our entire family relocated from Silicon Valley to my Upstate hometown by way of a 2 week cruise in an RV. He was then 6 years old so memories were a bit sketchy for him about that experience.

Now as a young man with an experienced traveler’s curious eye, Jared’s interest in a road trip evoked a positive reaction as soon as I brought up the idea.

While the ostensible reason was to transport a car we had in California to our home in Little Falls, I didn’t hide my interest in both the road trip experience and our spending some quality time together.

Because of winter weather risk traversing the Rockies this time of year, we took a southern route heading east along Interstate 40 and the old U.S. Route 66.

Desert and high plains from Las Vegas to Santa Fe were particularly scenic, and we veered off for side stops sometimes on a whim – like after seeing roadside billboards for the Billy the Kid Museum in Fort Sumner, New Mexico.

In comparison with cross country trips I did a decade or longer ago, I was struck this time by how much easier it is now with so many enhancements in the richness and ease of accessing information while on the fly.

We began the drive with no more planning than a general idea of the route and then made it up as we went along each day.

Google map features making it easy to pick up interesting attractions and stops along the route added to the process of discovery – so there was no difficulty in figuring out options we wouldn’t be experiencing back home, including dining in memorable settings like The Big Texan in Amarillo.

In picking the route we also stopped by to see a few friends, each of who had something to add to Jared’s experience. Our most memorable being time with my personal hero and mentor Jack Stack as we re-connected with him for the first time in about a decade.

The highlight for me though was the time Jared and I spent being together without distraction of outside influences. Sharing our observations, perspectives and thoughts in a relaxed way without the pressure of the next deadline or meeting.

We know that the convenience and relatively low cost of commercial air travel combine to put a big dent in long distance family road trips.

The wider range of leisure options we can easily find also builds a subtle time pressure to pack as much as we can into any time off period, perhaps sometimes with a feeling of being ready to tell others about where we’ve been over vacation.

Call me old fashioned, but I still like the road trip as a choice on the week or longer vacation menu. There is so much diversity in scenic beauty, attractions and culture right here in the U.S. Sharing with those we love is an experience best savored without tight timelines driven by flight schedule and limited time in a single location.

I’m a lucky guy to have a 23 year old son that shares that interest and still travels with his Dad. We made some memories together that will be with us always – and that’s what leisure time in our family is all about.


Returning From My Foray Into Politics

It’s almost a fist to the head kind of moment to realize I haven’t put a personal blog post up on this site since February last year.

Those that have regular contact with me know the story, but I suspect there are others on my distribution that weren’t aware of how my 2016 evaporated with my entire focus for the year spent pursuing a bid for U.S. Congress in New York’s 22nd District.

Adding to the improbability of the story was my choice to run as a third party candidate – seeking to buck the odds since no one has successfully done that in the last 5,000+ congressional elections since Bernie Sanders in 1990.

But then, entrepreneurs aren’t afraid to pursue the improbable and the entire effort was centered around my message of spurring job creation through the very things I’ve learned in my journey of starting and growing non profit Upstate Venture Connect these last seven years. Our mission there is to build scalable pathways connecting first time entrepreneurs to the resources needed to grow companies in new, fast growth industries. We are pushing Upstate NY’s economy in the direction that not only leverages our assets, but can actually succeed through private sector rather than government driven programs.

While I did not win the election, I’ve absolutely no regret for having run the gauntlet of a difficult, and sometimes vicious campaign fight that was an immersive and total learning experience from beginning to end.

Even though there is a most interesting backstory on how major parties and related special interests rig the system to stymie independents from advancing, I won’t be blogging much with retrospective campaign reflections or commenting on the dismal state of our political affairs.

Those people interested are welcome to browse through the Babinec For Congress site and if suffering insomnia, might watch one or more of our short documentary videos on Running Independent.

But I will share that the big motivator for me to run as an independent was realizing how the quirk in NY State’s election law permitting fusion voting actually gives minor parties a terrific opportunity to influence the political discourse by attracting major party candidates to co-list on the minor party lines.

So my personal quest in advancing the Upstate Jobs Party will continue and I do expect to put some posts up that share some of what I learned from my foray into the political world – including how entrepreneurs and others who care about job creation can make a difference at influencing a broader community without resorting to the quagmire of seeking change through public policy.

And since I’ve now re-engaged in growing Upstate Venture Connect and resumed investing and mentoring more startup entrepreneurs, you can expect to see more posts on these topics as well.

Looking forward to diving back in and hope to see comments and feedback as we re-energize building community.

It’s good to be back.


Overcome Seed Investor Bias

Overcome seed investor exit bias with vision and passion

As an active seed investor with my UpVentures, it’s not unusual for me to be weighing odds of investing in one company with some plausible acquirer targets on the horizon, versus another startup with a more speculative moon shot based on a large, but totally unproven, market opportunity.

This dynamic plays to entrepreneurs too. Wouldn’t a more likely pay day come in a space where others have shown some traction, ahead of being out there on the “bleeding” edge because you’re pioneering something that almost no one else sees yet?

There is no absolute here. Though as a seed stage investor, it is probably a good idea to have a portfolio with a mix of these two opportunity paths.

Investors can under appreciate market timing

Being ahead of the curve in a new and unfamiliar industry raises seed investor uncertainty about where the exit paths will be. This prompts a subtle bias for us to instead focus attention on opportunities that seem to have nearer term possibilities for liquidity.

But as IdeaLab founder Bill Gross recaps in this video reviewing data from 110+ companies he had a hand in, his search for causality in the factors of idea, team, business model, funding and timing (five classic early stage investor criteria) shows evidence that market timing had more to do with startup success than any of the other key criteria we seed investors rely upon.

Even one better is the wisdom of Paul Graham and his insights that come from decades of seed stage investing and running Y Combinator.

Overcome Seed Investor Bias

While multiple Paul Graham essays touch on this theme of market timing, one of my favorites is Black Swan Farming – he nails this seed investor bias against new models and markets by sharing logic behind his thinking why he felt Facebook was a lame seed investment opportunity when he first heard of it.

Biggest opportunities powered by multiple macro forces

While startups generally have some kind of societal, market or technological trend underlying their plausibility for being an investable growth business, if you parse through any list of $1B+ exits, you’ll see the big winners enjoyed a confluence of multiple macro trends that drove growth for an extended period.

Overcome Investor Bias | Learn from TriNet Founder Martin BabinecMy appreciation for this factor of multiple trend convergence began as it was probably the biggest reason prompting launch of my own startup journey in founding TriNet in 1988.

While very much a rookie entrepreneur then, I was more than a little passionate about how certain trends were both irreversible and directly related to powering our business model behind outsourced HR services including:

  • Increasing government regulations burdening employers
  • Shift in employment landscape from large companies to small
  • Smaller companies needing benefits to compete for talent (previously the domain only of big companies)
  • Technology adoption driving both speed of business (narrowing core competency that would in turn drive outsourcing) plus add new capabilities to enable efficiency in service delivery across a large number of smaller company customers.

As obvious as these trends might seem today, the late 1980’s was a different world and even venture investors couldn’t warm up to our opportunity since they didn’t then appreciate how our perceived pure service business could be sufficiently technology enabled to scale and leverage these converging trends as fully as TriNet proved to do.

Winning entrepreneurs articulate vision with passion

Vision and passion are important for any startup CEO. But if you’re forging new paths in unchartered models, you’ll be hard pressed to raise seed funding without a founder CEO getting across both these qualities.

Take the time to unpack specifics behind your supporting macro trends. Cite independent sources with data that supports your thesis. Tying multiple trends to defined elements of your business model and execution strategy boosts credibility in your vision.

But even those actions are not enough to sway seed investor interest if there isn’t a clear sense of deep personal passion on why this means so much to you.

Passion comes through when investors become convinced about the entrepreneur’s emotional commitment to the “why me” behind the problem the venture is solving. Our senses pick up the cues for this emotional commitment probably more so by how you articulate, than the logic supporting your argument.

A deep, passionate commitment is essential to overcoming the many obstacles ahead, including attracting the right team members who you’ll be asking to take their own risks in joining a team with an unproven model and/or industry.

Entrepreneurs who get seed investor attention are the ones whose vision and passion are so ingrained in their persona that they clearly differentiate from the crowd of their startup peers.

So don’t fear being “over the top” in getting across your passion and commitment. How you message that emotional commitment, coupled with a clear vision that ties specific trends to your model is what we’re looking for.

Winning investor hearts, along with our minds, is the combination that unlocks wallets to speculate with even greater risk than the semi plausible exit strategy we’re weighing you against as our investment alternative.


Prepping the Pitcher

Tips for pitch event organizers and startup founders from an investor’s perspective

Prepping the Pitcher - Tips for Your Next Pitch EventLast week I attended a local pitch event for the Upstate tech community that included four entrepreneurs pitching their startups. Like many other such events, the audience was a mixed group of entrepreneurs, community supporters and a small handful of investors. 

The pitches unfolded in typical fashion. When I saw the most common pitch errors across each of the four presenters, I did wonder about how the event organizers went about setting expectations and guiding the entrepreneurs doing the pitching. 

Entrepreneurs know these opportunities are important. They definitely spent time preparing, yet missed the chance to deliver a compelling case. Most importantly, none of the presenters specified what help they were seeking. 

What follows in this post are a few suggestions aimed at both event organizers and pitching entrepreneurs who seek to avoid the boring pitch syndrome.

Tip #1: Problem and solution are not enough

Entrepreneurs (particularly those with a technical background) fall too easily into the trap of using precious minutes in a pitch to dumb down the science. They hope to compel the audience by spelling out the technical challenges that were overcome, and the uniqueness of the startups’ product design.

If half or more of the pitch is spent defining the scope of the startup’s technology, it comes across like an academic exercise. The presenter is seen as working too hard to impress with his or her technical mastery – shortchanging the opportunity to secure support beyond defining problem and solution.

Tip #2: Pitch to investors, even in mixed groups

Even in situations where there is a mixed audience with diverse backgrounds and interests, I’m a fan of crafting pitches as if the entire audience were investors. 

Everyone wins by taking this approach in the pitch because: 

  • A standard set of guidelines can be provided to all presenters that directs them to a specific outcome
  • The event can run on a consistent track, making it easier for the audience to compare pitches with a lens that helps everyone think about how investors look at who to fund
  • The entrepreneur gets an opportunity to further hone the investor pitch, addressing things like business model, channels of distribution, margins and other critical business issues

Tip #3: Close with telling people what you want

I believe it’s essential to end a pitch with a specific appeal for help. Often times someone in the audience can assist the entrepreneur. They just need to ask!

Requests for help shouldn’t be limited to financing. Telling people what else your startup needs right now gets everyone thinking about how and who they know that can assist.

Whether it’s introductions to a specific type of customer or channel partner, or finding new team members, mentors and service providers, pitching is an opportunity to make a personal appeal. Someone in the audience may know the right resource for your company, but only if you tell them what you need.

Tip #4: Event organizers call the shots

With so many startups clamoring for the opportunity to get more exposure, event organizers have the leverage to set high standards for who they choose to present.

Instead of filling slots with whoever raises their hand first, consider inviting entrepreneurs to apply for the opportunity.

Even better, give them a short set of pitch guidelines on what you would like to see included in the pitch, and ask them to send a sample deck for you to evaluate.

It’s ok to tell applicants that their submission is just a sample. Ideally you and members of your supporting team can guide development of the final pitch so that it meets your target standard.

UNY50 - Experienced Entrepreneurs & Investors Provide Pitch HelpIf you need pitch mentoring support, resources like Upstate Venture Connect’s UNY50 Network or investors in any of our local seed funds can help. These same groups can also help recommend qualified startups to pitch.

Setting a high standard for your pitch events, and helping startup founders deliver compelling pitches will not only satisfy your audience, but reflect well on you as a sponsoring organization.


CatskillsConf: Fun mashup helps build startup community

Just came off a very fun and worthwhile weekend at the inaugural CatskillsConf – a three day affair that brought together an eclectic mix of creatives, tech people, foodies and startup community supporters.

Was cool not only because the organizers were able to successfully pull off marketing to assemble 120+ people that touched on all those themes, but the diversity included an audience nearly evenly split between Upstate and NY metro.

This was the first ever such gathering in the Hudson Valley/Catskills area. It came about after founders of the Hudson Valley Tech Meetup (Dan Stone, Daniel and Sabrina Shutzsmith and Kale Kaposhilin) met Aaron Quint, (web entrepreneur and former Paperless Post CTO/Chief Scientist) who recently transplanted from NYC to the Hudson Valley.

Pooling their combined organizational talents, passion for bringing people together and lists of contacts is what catalyzed CatskillsConf and their joint marketing outreach filled the room.

Leveraging Local Assets

Whether it was musical talent, farm to table culinary, wood crafts and natural settings of the Ashokan Center, this was a thoughtful mashup that brought diverse elements together with common themes that spoke to the millennial target.

On the learning side, my personal favorites were Dennis Crowley’s “put it all out there” story reflecting struggles at different stages in the startup journey, and also an amazing education segment featuring live birds of prey doing their thing.

birds of prey

When you’ve got a group together for more than a day, it gives opportunity to go beyond a large group learning setting to do some things that can be hands on, fun and social – all adding to the potential of building on strong relationships among participants.

The Catskills flavor for small group activities included options like foraging, blacksmithing, cider making, bookbinding, and drone piloting to name just a few.

Institutional ownership not a requirement for success

More than just a well run event, what’s unusual here is that the outcome wasn’t oriented towards benefiting a particular organization – but rather to just grow the relationship networks for participants, while having a fun time and creating many memories.

My boomer generation just isn’t used to seeing grass roots organizing like this without institutional ownership and resources.

New relationships will yield downstream benefit

As I browsed around, a frequent comment from local tech people sounded like “I used to think I was the only person around here like me. As a result of the groups forming and events bringing like minded people together, I’ve now got a growing network of supporters to help me.”

As I try to calculate the number of “creative collisions” that occurred and what happens when like minded people stumble into each other for the first time, there is little doubt that startup formation and growth will include some life changing outcomes sparked by what seemed like chance encounters.

Good things happen when a few people step up to lead

Kudos to the organizers as they took financial risk and put in a ton of hours along with a full supporting team of volunteers.

They set an inspiring standard for others to follow and their leadership adds further fuel to my optimism about why it is the millennials who are making the difference in powering Upstate towards a big jump in the number of new industry companies and jobs that will rise here from humble beginnings as people meeting at an event that then lead to collaborating on a startup.

We pledge our resources at Upstate Venture Connect to support their efforts and look forward to doing the same for all others ready to lead the charge in their own local market.


Recognizing Startup Community Builders

With a twist on the traditional “Entrepreneur of the Year” awards celebration, Upstate Venture Connect has partnered with Upstate Venture Association of NY to do our first ever celebration to recognize people who are making a difference in building our burgeoning startup ecosystem across the Upstate region.

Entrepreneur leaders make things happen by powering the launch and growth of activities and initiatives ranging from Startup Weekends, angel investor funds, accelerator programs, tech meetups and hackathons to name just a few from the diverse range we already see here in Upstate NY.

Who comes to mind in your community that is out front and leading with their actions to help startup entrepreneurs launch and grow companies?

You can nominate them here for one or more categories in our Venture Ecosystem Awards.

All too often, startup community leaders are people motivated by no more than wanting to leverage their time and talent to make things happen. Our goals include putting the spotlight on those making a difference as well as sharing examples that will motivate others to step up and lead.

Don’t delay as nominations close Monday August 31. The nomination format is easy – if you know someone making a difference they will be in good company.

Sign up yourself to attend our October 9th celebration luncheon at Turningstone Resort in Vernon. We anticipate a turnout of 2-300 people who are leaders and supporters from throughout the Upstate startup ecosystem.

Join us in the fun and show support for those that are building Upstate’s startup economy.

See you there!