With in-person events returning, investor introductions will require more than the perfect cold outreach email. When you’re face-to-face with a prospective investor, finding the right opening to pitch your vision, convey traction, and make a clear ask is a tall order—especially at large events.

So, we surveyed our network of top-tier investors to see which in-person introduction strategies Do and Don’t work to help you stand out from the crowd.

DO consider the context carefully. 

To make a good first impression, avoid bathroom pitches, interrupting family occasions, or any tactics that border on stalking. Trust us—these tactics are a huge turnoff and only serve to hurt your cause. Instead, look for moments when there’s a natural opportunity for an introduction. 

DON’T jump right to pitching. 

As with all networking, people are more likely to engage with folks they like and want to be helpful to, so a good first impression works in your favor. When in doubt, ask about the investor’s current focus or interests, then see if there’s a good fit between their response and what you’re building as a segue to your pitch.

DO personalize your talking points. 

The smartest founders know their audience and tailor their pitches accordingly. Convincing an investor that your startup fits their portfolio is key to securing a meeting. So, do your research via LinkedIn, Crunchbase, etc., to understand each fund or individual investor’s thesis and past investments to make the case for a perfect fit. The more relevant connection points you can draw, the better.

DON’T recite your pitch deck to them. 

Your elevator pitch should succinctly touch on the scope of the problem, your vision for a solution, your founding team’s unique insight, product-market fit, and the dominant value proposition to your customer or user. Try quantifying your value proposition to further emphasize traction and make your solution tangible, i.e. save x% of time or increase revenue by x%. Explain your solution as it is today and how you predict it will likely develop over the next 3+ years. Once those bases are covered, don’t forget to ask if they have any questions! 

DON’T be afraid to say, “I don’t know.” 

Taking a chance on a founder comes with inherent risk. To mitigate potential wild cards, investors are also screening founders for honesty and transparency. If a founder seems to be withholding or misconstruing information, it’s a pretty big red flag. So stick to what you know. 

DO choose your words carefully. 

While you want to appear confident, many investors note that overcompensating in the following ways can quickly kill interest:

DO end with a clear and direct ask. 

Whatever you do, don’t leave an investor wondering, “What is the ask from me right now?” To transition to your ask, share how much you’ve raised to date and any key investors you’ve already lined up. If you’re currently raising, make the terms of the round clear. Be specific in your ask and remember: the worst they can say is no.

To recap, keep these 10 things in mind before you approach a potential investor:

These may seem like a lot of Do’s and Don’ts to juggle, but the bottom line is simple: be clear, concise, and courteous of an investor’s time. Remember that the primary goal of your cold introduction is to pique their interest enough for a call or a meeting, so focus on being straightforward and factual without getting too far down in the weeds.

Next, check out the Ask an Investor: Cold Outreach Do’s + Don’ts Field Guide to craft the perfect follow-up email!

As a team of former startup founders, we know how time-consuming raising capital can be, especially for early-stage startups relying heavily on cold intros to investors.

OutPitch 3.1 is how we’re leveling the playing field.

FOUNDERS: OutPitch 3.1 is your chance to turn 1 pitch → 200+ investor introductions.

If you’ve got what it takes to outvision, outbrave, outperform, outsmart, and outpitch the competition, start your OutPitch 3.1 application now!

Here’s what founders need to know:

APPLY x OutPitch 3.1

INVESTORS: OutPitch 3.1 is your chance to turn 1 hour → 5 group-vetted, early-stage deals!

For 14+ years, we’ve honed the ability to write first-checks at the earliest stages of future unicorns, so investors know our finalist picks will be 🔥.

Here’s what investors need to know:


Save your spot now to invest in real-time in five Outlander-vetted startups at OutPitch 3.1:

RSVP x OutPitch 3.1

To learn more about Stonks events, visit Stonks.com. For OutPitch 3.1 questions, reach out to our team at info@outlander.vc.

After a fierce live competition from our five early-stage tech startup finalists, here’s the pitch that won Levantr the title of OutPitch 2.0 Champion:

In case you missed it, watch every pitch and view every deck of OutPitch 2.0 here

As the virtual applause faded, we caught up with founder and CEO Jennifer Hong and the OutPitch judges to dig into what this win means for the Levantr team.

Why were you inspired to build Levantr?

I went to an international school for a few years growing up. Most of my friends were ex-pats and diplomats’ kids, so traveling has been a big part of my life since I was young. Because of that, I really believe that seeing new places and meeting people from very different backgrounds makes a person less prejudiced and more intellectually curious. So I wanted to inspire more people to travel farther, explore the unfamiliar and grow from experiences shared with old and new friends. 

I’ve organized/planned maybe 50 trips with friends and family and wanted to pull my hair out each time. Planning should be fun. We are the happiest during planning—even more than while traveling—because it’s pure excitement and hope. At Levantr, we want to help and reward people who care about their travel experiences from start to finish, which first means freeing them from endless spreadsheets.

All of the judges really liked the fact that Levantr’s product has a social hook. Planning a trip is inherently a group activity. Inviting new members to the platform isn’t just a growth hack but a necessary product attribute, which we believe will lead to low user-acquisition costs over time. 

We also like that there were many obvious business models that could get spun out of the business. For example, Levantr could develop into an OTA, a media business, or a lead-generation business for touring activities, just to name a few.

In addition to the scalability of Levantr, we agreed that Jen had the appropriate growth background to execute on the vision and build a successful business.”

 – Ali Hamed, Coventure and Crossbeam VC

What is your long-term vision for Levantr?

Levantr, in its current form, is a productivity tool for travel coordination. As such, we get a behind-the-scenes look at our users’ travel plans—their dream flights, hotels, excursions, eateries, and so on—and key insights into how they’re making their travel decisions, allowing us to a powerful personalization engine for travelers.

We’re essentially creating a new kind of decentralized, demand-driven marketplace for travelers with personalized deals and inter-user inspiration. Looking forward, we believe Levantr will become the ultimate marketing channel and marketplace for all types of travel providers and complementary businesses, such as hotels, tour operators, travel agencies, influencers, ancillary services, the hospitality industry, and even OTAs. We’re thrilled to kick this journey off with our partners at Shanti Global Hospitality, which includes 30+ hotels and travel brands, and the upcoming pilot marketplace featuring international hotel partners Nira Caledonia, Shanti Maurice, and more! 

 At Outlander, we believe strong founders are the primary determinant of successful companies. 

With Levantr, I was super impressed with Jen’s background and how it has informed her thinking in building out the Levantr marketplace model. Throughout her pitch, she demonstrated a strong understanding—and many first-hand experiences—of travelers exasperated by trying to coordinate and organize group itineraries.

And although Levantr is a very early-stage company, Jen’s smart, early execution and intelligence around which pieces of her company to prioritize initially makes me believe she’s got what it takes to build something big. 

We’re super excited to welcome Jen to the Outlander family!

– Leura Craig, Outlander VC

Why do you want to work with Outlander VC? 

When we started looking for early-stage investors, Outlander VC came highly recommended again and again. As an early-stage company creating an entirely new business model, we knew we needed investors who understand how to support an early-stage founding team and add value to our growth. For us, that’s Outlander VC.

What drew you to OutPitch 2.0?

Funnily enough, I actually attended the first OutPitch! I remember thinking it would be such a great opportunity for Levantr, so I immediately messaged them about the next one on Twitter. A few months later, we applied as soon as it opened. 

To now win OutPitch 2.0 is surreal. We had just begun our fundraising journey, so winning this pitch competition strengthens our conviction that Levantr can help the industry. The whole experience and the Outlander VC team’s excitement have made us more energized and motivated to tackle the next hurdles and accelerate our growth!

________________________________________________________________________________________________

Thank you again to all five of our OutPitch 2.0 finalists, who made our judges’ decision incredibly difficult by representing the most innovative early-stage tech startups across the US.

Watch each finalists’ live pitch and Q&A here:

Until next time, keep hunting and stay outlandish!

OutPitch 2.0 replay

First impressions matter—especially when you’re making a cold introduction to a potential investor. And in order to make sure you put your best foot forward as a founder, you must broaden your scope from merely raising funds to building lasting relationships.

We surveyed our network of pre-seed investors to determine what elements of a cold outreach are most likely to work in a founder’s favor and what aspects of a cold intro compel them to immediately delete. Here’s what they shared with us:

The Do’s

The only thing that works in a cold outreach is heavy background research on the target so that you can carefully customize the inquiry. – Lister Delgado, IDEA Fund Partners

  1. PERSONALIZED PITCH – The most common feedback from investors revolved around personalization. Almost every surveyed investor wanted to know, “Why is your venture a good fit for my investment thesis and vice versa?” Ultimately, raising venture capital is about more than just the check. So starting with the cold introduction, respect investors’ time by doing your own due diligence and only pursuing mutually beneficial relationships based on their interests, too.
  2. PROOF POINT METRICS – Be sure to include top-line metrics that convey early traction, such as positive revenue, customer growth, consumption growth, engagement growth, growth efficiency, and user experience, etc. As with choosing a North Star Metric, do not focus on the vanity or laddering up metrics but on the metrics that highlight your company’s rate of growth.
  3. WHY YOU? – Briefly highlight your founding team’s background and caliber, but remember that investors are looking for ambition, not personal ego. Keep it concise by including the founding team’s LinkedIn profiles, plus any pertinent personal story that contextualizes your company’s vision and growth up to this point. 
  4. BRIEF COMPANY OVERVIEW – Obviously, make sure the central info is there, like your company’s name, a link to your product and/or website, your company stage, and your current location. But, keep it short and sweet (3-4 sentences max) and let your website/deck elaborate further.
  5. FUNDING ROUND + HISTORY – If your terms are set, feel free to include them as well as what allocation you have left. Give investors an idea about your total target raise, timeline, and how far along you already are. 
  6. VISION + CONTEXT – As always, the why is essential. What are you building, and how does it offer a value add to customers? Include who your first target customer is/will be and why. Break down your company’s market briefly, unless you’re reaching out to an investor who is already actively working in that specific industry. 
  7. CONCISE MESSAGE + DECK/DEMO – Include a clear, concise pitch deck that provides an attractive summary of the items listed above and/or a demo of your product. And remember Alex Camacho’s advice: the sweet spot for an introductory email is around 800 characters.

The Don’ts

Your goal from the email is a call or meeting, so don’t be over the top, don’t ramble, don’t give everything away, and avoid long, form emails and super rapid follow-ups. – Betsy Hoover, Higher Ground Labs

  1. EMPTY PROMISES – First and foremost, don’t jump into a cold intro with tons of exaggerated statistics or promises about what you can deliver. Scarcity tactics, gimmicks, and sales stunts are also an absolute NO. Investors will be quick to see through anything along those lines, and then they’ll be even quicker to pass on you.
  2. MASS EMAIL BLASTS – Investors will immediately know if you’ve just BCCed them on a mass email that’s in a boring template, and it’s a definite turn-off. Spend the time and energy it takes to learn about each investor and be sure you’re able to speak to exactly why they’d be a good fit to partner with your company. 
  3. NO DECK, LITTLE INFO – While our surveyed investors universally dislike long introduction emails, you’re also unlikely to get a response from one lacking the elements on our “Do” list. Investors’ time is precious, and they’re not going to give you a shot without at least some idea about what it is you’re seeking and why. So don’t expect a meeting if you haven’t sent over a thorough deck or substantial summary info. 
  4. CLASSIFIED INFO + NDA – Don’t ask an investor to sign an NDA on a cold email. Your goal for initial contact should be to gain their interest, and the summary information you’re sharing shouldn’t require an NDA.
  5. DISREGARD INSTRUCTIONS – If a VC’s website or LinkedIn directs founders to submit information in a specific way, do not circumvent that process. After some time has passed, you can follow up with a very brief email or message.
  6. SPELLING/GRAMMAR ERRORS – This should go without saying, but have someone glance over your email or use a program like Grammarly to make sure you’re expressing yourself as eloquently as possible. 
  7. RAPID FOLLOW-UPS – No one—and I repeat no one—wants to be pestered into responding to an email by being continuously peppered. Just don’t do it. 
  8. BROKER REACHING OUT ON FOUNDER BEHALF – Don’t have someone do this work for you. If you’re the leader of your company, you need to be sending this email and building this relationship.

These may seem like a lot of Do’s and Don’ts, but the bottom line is simple: be clear, concise, and courteous of an investor’s time. Remember that the primary goal of your cold introduction is to pique their interest enough for a call or meeting, so focus on being straightforward and factual without getting too in the weeds. Finally, if you want to grab their attention, do your research and personalize your pitch! 


Ready to test out your new-and-improved cold outreach? Send your best pitch to
info@outlander.vc!

For more expert advice on building and scaling your startup, check out our event library and Field Notes.

For July’s Outlandish Speaker Series, Alex Camacho taught early-stage recruitment 101.

Watch the replay for all of his best practices for building successful early-stage teams or hit the highlights from our Q&A below.

Alex is the CEO and Founder of AC Consulting Group, a recruiting firm specializing in scaling early-stage venture-backed startups. He works directly with founders and functional leaders to fill their highest priority roles with the highest-quality talent in tech. Through his hundreds of hires for many dozens of tech startups via AC Consulting, Alex has seen just about every recruiting scenario a startup might find itself going through. 

Though most of Alex’s clients are Seed and Series A, he’s successfully worked with clients ranging from late-stage growth companies down to building Pre-Seed companies from scratch. His hires range from just about anything you can imagine an early-stage company would need— including non-tech roles like Head of Recruiting, VP Sales, VP Marketing, and many more—with a primary focus in engineering and product recruitment. 

Overview

Challenges of early-stage startup recruitment:

I’ve spent a lot of time in the early-stage recruiting space and have had the pleasure of working with some fantastic VCs and founders. The way I look at it is the future Zuckerberg’s and Musk’s are in this tech space, and I’m a huge believer and investor in technology because, of course, it’s the future. But focusing almost exclusively on early-stage startups’ recruitment comes with a unique set of challenges. 

First, it is extremely difficult for an early-stage startup with minimal notoriety to get responses to job postings. Second, a growing number of professionals—especially in the technical realm—just don’t reply to recruiters. Instead, they want to hear directly from the startup’s founder, which leads us to the third challenge: recruitment is a full-time, specialized job that founders do not have time for. 

And that’s where I come in. Using a dummy founder email address, I’m able to execute recruitment marketing campaigns to source and filter through candidates on behalf of the founder. Then, founding teams meet with the top candidates and—more often than not—invites them to join their early-stage team. Since I began recruiting this way, I’ve iterated and perfected my early-stage recruitment funnel method.

Best practices for structuring an early-stage startup recruitment funnel:

  1. Create a broad, flexible profile of your ideal candidate with the goal of finding the highest number of viable leads. The keywords here are broad and flexible, meaning your profile is not rigidly set in specifics. For instance, I recommend being as language agnostic as possible. If the person doesn’t fit exactly what you’re looking for but seems really sharp, adaptable, and autonomous, then keep in mind that the ramp-up time to get them up to speed might be shorter than the time it takes to restart a search to find someone with the specific skillset already. 
  2. Build email marketing campaigns that are short and compelling. Begin with 2-3 sentences that convey traction; leverage growth metrics, impressive VCs or employees involved, etc. that will make them think, “This is a startup I cannot miss out on.” Follow with your layman’s pitch, which should answer 1) What is the huge problem your startup is solving? and 2) How is your startup the best positioned to solve that problem? Keep it short (~800 characters or less) and avoid vague cliches that could apply to any startup.
  3. Design your interview process to keep high-quality candidates engaged. Early-stage recruitment is a candidate-centric market, meaning the onus is on you to sell your startup to the high quality and in-demand candidate and not vice versa. Your ultimate goal is to convert somebody into a hire and feel good about what they’re bringing to the table.
  4. When closing the deal, remember that you are competing in a candidate-centric market to convert ideal candidates to employees. So make them an offer as soon as possible, and pay at a percentile that matches the percentile you want to recruit. High-quality candidates in the 99th percentile will be more expensive than the 50th percentile, and they’re going to have a lot more demand, so if you want to hire high-quality people, don’t pay the 50th percentile.

For more details on structuring your early-stage recruitment funnel, watch the replay of Alex’s live explanation of the funnel here [6m 49s].

Q&A

What is the one question you would ask above all others when hiring the first executive-level employee at a startup?

For candidates with a background in startups, I’d ask, “What is the best example of a time when you single-handedly changed the trajectory of a company that you work for?” and then push them for excruciating detail. They should be able to explain the impact top-down—a good executive person would understand their impact on everyone’s roles all the way down the line in low-level detail. 

For candidates without a background in startups, the first question may be less relevant. So instead, I’d ask them, “What was the most impactful thing you’ve done in your previous roles?” and then push them for the same level of detail as the first question.

In whatever way makes the most sense, dig into their previous experiences to learn what size/kind of impact they’ve made in their previous roles, how they did it, who helped them get there, and, ultimately, will they be able to recreate that impact? Will they be able to tackle major challenges, implement a plan, and then execute on it? Are they willing to roll up their sleeves? Do they need a team? You need to get a sense of how they functioned in previous roles and whether that function makes sense in the context of your company.

How much equity should we think about for early-stage hires, and do you think it’s necessary to include it in all hiring offers? 

In my opinion, you should give equity to everybody on your team. Even if it is just a few shares, it will make them feel bought into the startup’s success. As far as how much you give, that really depends on your valuation and the market value of the employee, i.e. their position and value-add to the company. 

Our most significant recruiting pain point is the competitive recruiting market. So how do we incentivize long-term retention?

People will retain themselves if your company does well, so treat your current employees well and hire good people around them. From a recruiting perspective, treating your team well means avoiding any stagnation of headcount and losing good team members unnecessarily. I always say, “Losing people based on compensation is very expensive.” If somebody wants $10K, $15K, or $20K more, and that makes you a little uncomfortable, trust me when I say that the people who work at your company want to see that potential for growth within the company. So paying current employees a little bit more to retain them will help you in the long run. 

So treat your current employees well, give refreshers, give raises, and grow your company! 

Our most significant recruiting pain point is finding executive leadership acumen with a startup operations mindset. So how do we find/connect to talent outside of Atlanta, such as recruiting from bigger markets like LA, SF, NY? 

I highly suggest building remote teams. The concentration of tech folks in the San Francisco market versus the next market down—such as New York, Seattle—and sub-markets like Austin, Denver, Portland, Boston, etc. is night and day. Plus, with remote learning becoming more and more accessible, the perfect fit could literally be anywhere. If you want to scale a technical startup, you need to look outside your local geo and figure out how to incentivize top-tier employees from top-tier markets.

I’m a little bit biased, but my advice would be to hire outside help to recruit from these markets. Beyond that, I’d suggest leverage your network—and especially your VCs networks—to find candidates from outside your geo that are worth the investment of recruiting and converting to hires.

What are the best practices for recruiting inside sales?

Find hustlers. Find somebody willing to grind and who is sharp and capable and has a chip on their shoulder. Somebody who is a little money motivated because, for inside sales, they’re going to need to be. In my opinion, try to hire someone right out of school who cares about growth and being the best at what they do. Hop on LinkedIn and shoot out some messages, then it should be easy to find folks who fit this personality.

What are the best practices for recruiting co-founders? 

It’s the same as recruiting anybody, but you need to spend a lot more time with them. Generally, the more senior the position, the more acceptable it is to have a more prolonged and intensive interview process. The standard interview process doesn’t apply to co-founder recruitment because you need to spend way more time with them and really get to know them. For example, my former co-founder spent like 20+ hours walking around the park and doing all kinds of stuff to get to know me better. This is the person who will be co-running your startup, aka your baby, with you, so you need to spend a lot of time getting to know them as a person before pulling the trigger. Ideally, you should probably consider potential co-founders that either you already know super well or someone you know and trust also knows and trusts them, too. 

For more expert advice on building and scaling your startup, check out our event library and Field Notes.

A startup’s early momentum relies not only on the founding team’s outlandish vision but also on how effectively that mission is articulated in its external business strategy. From the tone of your messaging to how you visually display your solution, every contact point you have with potential investors and customers creates the overarching narrative that influences how they perceive your brand. 

Building a great brand narrative starts with nailing down the top 2 to 3 values you want to convey and the belief that echoes these values: What belief is your mission built upon? Why do you care about it so much? How will your startup deliver on its promise? These are the impressions you want your audience to take away from your collective marketing efforts.

Like your startup, these branding attributes may eventually need to pivot. In fact, pivoting your business may necessitate a brand refresh to remain true to your mission. However, rebranding is not a decision to be made frequently or flippantly. A poorly timed rebrand will cause logistical challenges that end in losing brand recognition, breaking web assets, and confusing existing customers. But if your brand narrative no longer aligns with your mission, then rebranding becomes necessary for your marketing to remain effective.

For one of our portfolio founders—Akshita Iyer of Ome—the decision to rebrand her early-stage startup felt inevitable:

“As a consumer-facing company, it’s not just about the solution you’re building, but what your company’s brand identity tells potential consumers and the feeling evoked by simply saying its name. All of it has to be sticky.” 

In the aftermath of her mother’s kitchen fire in 2016, Akshita Iyer set out to create a solution to help other families avoid a similar tragedy. Her team developed a smart knob for gas and electric stoves that turns them into smart appliances within seconds. By syncing directly to your smartphone, the smart knobs give you total control of your stove from anywhere.

The first iteration of Iyer’s startup was called Inirv, which pulled from the medical term “innervate” and describes how nerves connect different parts of the body and allow them to communicate with one another. The name reflected the technical aspects of her startup’s solution, but as Akshita began pivoting to a consumer-facing market, she knew that something was off:

“As my vision for what the company could become evolved, I started to feel uncertain and apprehensive about the name because we were no longer just building a product, we needed to build a brand and an identity. I just never felt like Inirv fully encompassed our vision or mission.”

Realizing she was at a pivotal moment just before mass production of their inaugural product and rebranding would become a logistical nightmare, Akshita decided to pull the trigger on a new name and look. However, she quickly began to worry over finding the right name and aesthetic for her venture. So, back at the drawing board again, she reached out to our very own Leura Craig here at Outlander and asked whether she should seek out a marketing agency that could approach the project with a fresh perspective. 

Leura shared two crucial pieces of advice with Akshita:

  1. First, you’re a startup, and big-box agencies are far from affordable. 
  2. Second, don’t you want to have a hand in coming up with a name that means something to you?

Akshita took two weeks to make a list of dozens of words that came to mind when thinking about peace of mind, safety, cooking, or simplicity. Her team even dug up some names from the past to re-evaluate their potential. Unfortunately, like many early-stage startups, they repeatedly ran into trademarking roadblocks because major appliance brands had gobbled up so many of the terms they came up with. Additionally, Leura reminded them that they also needed to be able to acquire a strong domain. Eventually, Akshita went so far as to send out a mass text to her friends and family members asking them to send her any word they could think of that might be connected to the company in some way. 

In response to Akshita’s all-call for branding ideas, her sister-in-law sent the word “OM,” as in the sound that’s frequently used in meditative practices. Akshita thought it was interesting because of its connection with a sense of peace and serenity, which her venture’s products aimed to bring to consumers. Still, she worried it was already too heavily associated with other things, like yoga and meditation practices. But after reaching several other deadends, she looped back around to it and started to consider how it might be able to work. 

“From a meaning perspective, I realized that it aligned deeply with what we’re trying to do: at our core, we’re bringing peace of mind and tranquility to your home. I also knew that if someone heard the name, they would understand it, but I was worried that just seeing it, they might not know how to pronounce it. So I thought, well, why don’t we add an E to the end, simplify the pronunciation, and let it be a derivation from that word?”

And so Ome was born.

From there, Akshita turned her attention to the look of the brand, which had initially been envisioned to feel very “techie” in nature with its sharp font and bright blue gradient.

She realized that the visuals weren’t matching the feeling they wanted their company to convey, which was a sense of calmness. So her team shifted to soft, curved, and lowercase lettering and incorporated gradient colors going from blue to purple. They even managed to make the O in Ome a subtle nod to their first product: a circular, smart stove knob.

For Akshita, the brand instantly became warmer and more understandable. Consumers didn’t need to know all the technical details behind the product to benefit from it; they just needed to get a sense of what their experience would be like owning the product: simple and worry-free. So they continued to build out their messaging using the new name and a focus on value their product brings to consumers—ease, simplicity, and peace—and purposefully avoided aesthetics and messaging reliant on fear-mongering. 

“I started to think, what if we come out with a new product down the line that works with our system to make cooking more efficient — like a sensor that can detect the temperature of your meat? I didn’t want to box us into being exclusively about kitchen safety. Our vision is to create products that all funnel up to creating peace of mind and building better kitchens for busy families.”

In the end, it was Akshita who gained some peace of mind about her company’s future and its message to the public. Previously, she’d struggled to envision Inirv becoming a household staple name. But with Ome, the pieces finally started to fit together for her startup to take the next big step. Not to mention, it renewed her confidence in the mission she set out on several years ago.

Her advice for fellow startup founders considering a rebrand? Go with your gut:

“If in your gut you feel like you need a name change, do it. Our rebrand had a significant effect on my ability to lead; I strongly believe that as a founder, you need to feel that spark of inspiration every time you see your company’s name.”

You’ve probably heard the phrase “Branding is everything,” and it is without a doubt a pivotal part of the startup journey. But rebranding choices aren’t to be made frequently or flippantly. Akshita’s team chose the right moment, avoided major trademark and domain pitfalls, and ensured they stayed true to their overall mission and narrative. In short, they utilized their rebrand to speak to their potential customers with a clearer and more compelling message that will ultimately lead to greater success for their brand.

Out of 150+ applications and fierce competition from the six early-stage tech startup finalists from across the Southeast, here’s the pitch that won City Shoppe the title of OutPitch 2021 Champion:

As the virtual applause faded, we caught up with CEO and co-founder Ash Cintas and the OutPitch 2021 judges to dig deeper into how City Shoppe out pitched the competition and what this win means for Ash and her team.

Why were you inspired to build City Shoppe? 

As a former small business owner, I was frustrated with the lack of support and platforms for small business owners (SMBs) to manage and compete against the pay-to-play of eCommerce. My business was too grown to be on Etsy but too small to make a dent on Amazon. Why wasn’t there an option for small-to-medium-sized businesses to fit in? 

As a conscious consumer, the rabbit hole of search engines and social media made it impossible for me to find the brands or retailers I aligned with, and I didn’t want to or have the time to spend hours searching. I thought to myself: Why does local shopping have to be limited to my physical proximity in a digital world? Why can’t I shop local value-driven brands from around the country, all from one site?

City Shoppe has demonstrated impressive traction in solving acute pain points for small business owners. Their timing and trends have remained aligned in spite of challenges like the pandemic, focusing on loyalty to local businesses in every iteration of developing their robust solution. Plus, Ash is a strong founder with domain expertise! “ – Ariana Desiree Thacker, Guest Judge from Conscience VC

What keeps you and your team at City Shoppe going on hard days?

What keeps us going is the community and support we are building for small businesses that have notoriously been left out to bring their products worldwide. It brings excitement and reassurance that the City Shoppe team is creating a life-changing experience and company when a seller on City Shoppe gets their first sale from a customer halfway across the country, who usually would have never known about them and their products.

“Personally, I am always looking for more ways to shop locally and by impact, but I have struggled to find great makers and products. City Shoppe clearly helps solve the needs of so many small business owners by connecting consumers to the products they want more than ever.

As a founder, Ash has the right set of experiences and vision for building a company like City Shoppe. Plus, the founding team’s demonstrated ability to execute quickly and their solution’s early traction is something we always look for when investing in early-stage startups. We are super excited to welcome Ash to the Outlander family!” – Leura Craig, Judge from Outlander VC

Why do you want to work with Outlander VC? 

What drew me to Outlander and their OutPitch competition was their team’s vision. They could see our idea for a different world of e-commerce created by the collective of small businesses, which not only employ most of the US workforce but they’re also the hearts and souls of our communities. From the beginning, Outlander’s in-depth analysis of our market showed authentic engagement and belief. 

Being a Southern woman at heart, growing up in Virginia and North Carolina, and now building our HQ in Austin, I knew the Outlander’s intentionality and passion for funding underrepresented founders in the Southeast made them the perfect fit to work with. Winning OutPitch, I look forward to the Outlander team’s guidance, mentorship, and support to help push City Shoppe to the next level. 

“Many small businesses don’t have the resources or experience to effectively manage their digital commerce. City Shoppe is helping fill that gap via services and technology. The team has a deep understanding of the problem and relevant experience that qualifies them to solve this problem. They’ve executed quickly during uncertain times and early metrics indicate they’re creating value for the small businesses and consumers they serve.” – Jermaine Brown, Judge from Outlander VC

What is the long-term vision for City Shoppe?

City Shop’s long-term vision is to redefine what it means to buy and sell online (instead of our current siloed and fragmented platforms) by building a digital community of shared resources, engagement, and connection for businesses and consumers globally. 

Nine months ago, our team of seven came together to change the way the world shops local and to give small businesses a fighting chance to succeed in eCommerce. I want to spotlight and thank the City Shoppe team for their tireless work, passion, and belief in what we are building. The fun has just begun!

Thank you again to all six of our OutPitch 2021 finalists, who made our judges’ decision incredibly difficult by representing the most innovative early-stage tech startups across the Southeast. Watch all six finalists’ live pitch and Q&A here:

Thank you to our brilliant panel of VC judges, including Ariana Desiree Thacker from Conscience VC and Jermaine Brown and Leura Craig from Outlander VC, for your thoughtful questions for each finalist, as well as Paige Craig for a lively and insightful Q&A with our OutPitch 2021 audience. #TeamCockroach

And thank you to our audience of 200+ investors and founders for tuning in from around the globe to cheer on our innovative OutPitch 2021 finalists.

Until next time, keep hunting and stay outlandish!

As we lap the one-year anniversary of the global shutdown and shift to working from home, companies are evaluating the long-term pros and cons of employing a distributed workforce, and according to Chris Herd, “Remote work isn’t going anywhere.” As the founder of Firstbase, a startup helping companies manage remote employees, Herd reports that even during lockdowns and while juggling homeschooling kids, 80-90% of people have reported that they never want to work in an office full-time again, and 46% of people want to work from home at least part-time. And he predicts those numbers are likely to grow further once the benefits of remote work post-COVID are fully realized. Since remote work is here to stay, we must figure out how to make it work for all of us.

Isolation, Burnout, and Productivity

Though many prefer WFH to an office commute, the transition has had unforeseen impacts on how we work individually and as teams. The research Microsoft began at the beginning of the pandemic shows that most of their new remote workers reported a lack of physical cues, body language, and ability to gauge emotional responses in remote communication methods as significant hurdles to productive disagreement and decision-making. Likewise, a recent analysis by TINYpulse also found that employees onboarded remotely mid-pandemic were not absorbing their new workplaces’ culture and values, attributing it to those onboarded after COVID-19 being less connected with their teammates. According to a report released by employee experience company Limeade, the culmination of these factors leads to increased burnout levels: 72% reported experiencing burnout—up from 42% in a similar survey before the pandemic.

“We are all right now participants in a giant, natural, uncontrolled remote work experiment from which [we] must learn.”

— Microsoft

With 1 in 4 Americans set to continue WFH in 2021, there will be an even stronger call for the development of innovative tech in order to battle growing burnout and isolation rates. Here are Remoter’s top five cultural aspects that “challenge” an enjoyable remote day to day that they recommend company leaders work to address:

  1. Constant video calls—replace video with audio-only calls whenever possible. 
  2. Lack of asynchronous communication—privileging synchronous communication (like phone calls, video calls, and live chat) negatively impacts your remote team’s productivity and contributes to increased burnout levels.
  3. Team member disconnect—even your office introvert is missing some old-fashioned human interaction, so try establishing “virtual coffee breaks” and work-free virtual happy hours as a team practice.
  4. All work and no play is causing burnout—create a self-care and watercooler chat for team members to take a break mid-workday and share their remote work tips.
  5. Respect people’s non-work time—work/life balance is tricky when your home is also your office, so set clear guidelines about avoiding after-hours requests for items that don’t need immediate attention.

Teams communicating exclusively through digital mediums must adapt to incorporate meaningful interactions between team members and recreate the ease and clarity of in-person idea-sharing in our new virtual workplaces. Here are a few tools to get the ball rolling with your remote team.

Remote Communication Hacks

How do we adapt our remote work processes to recreate the ease and clarity of in-person idea sharing in our virtual workspaces? We’ve included some of our favorite tools for collaborating virtually that help to minimize the top challenges for enjoyable remote work.

Loom is a video messaging tool that helps you get your message across through instantly shareable videos.

With Loom, you can record your camera, microphone, and desktop simultaneously. Your video is then immediately available to share through Loom’s patented technology like the video to the right.

Loom’s technology is excellent for all your asynchronous communication needs, like nailing a virtual pitch (looking at you, founders!), sharing project updates with your team, and troubleshooting technical issues. Not every update needs to be a video conference, and, frankly, operating that way can be a colossal waste of time and energy. One of our remote workforce’s top requests is for fewer video meetings, so embrace the asynchronicity and send a Loom instead!

Meet your new meeting-scheduler, agenda-setter, and note-taker: Notiv.

Through collaborative pre-meeting agendas and calendar syncing, Notiv ensures all attendees are prepped and ready for a meeting before it begins. When Notiv joins your video or phone meeting, the application automatically records the meeting’s content and highlights important decisions, action items, and insights. After hanging up, Notiv creates a searchable transcript from the audio recording, which can be shared and reviewed quickly to get the full context behind all your team’s decisions.

Notiv’s technology not only makes pre-meeting planning and collaboration simple, it also frees your team up to be fully present mid-meeting by alleviating the need to take detailed notes. Plus, with Notiv’s searchable transcript and assignable action-items, your team will always be on the same page.

Want to see an example of Notiv’s transcription? Check out the recordings and Notiv transcriptions of our last two Outlandish Speaker Series with Lo Toney and Hamet Watt.

Teemyco is bringing all the perks of working IRL to your own virtual office.

Complete with brainstorming rooms, focus areas, meeting rooms, and, of course, a kitchen for coffee breaks and office banter, each virtual office is fully customizable to accommodate your company’s, team’s, and individual needs.

Teemyco’s virtual office replicates co-worker interactions and the team presence of working in the same building, like popping into your favorite coworker’s office to chat without the back-and-forth scheduling and meeting links. Your team appears as icons that can move from room to room based on their workstyle mood. Shift your icon to a quiet zone when you need to concentrate without people trying to ping you, then move over to the kitchen when you’re in need of some fresh office banter.

Help your team maintain what is left of their work/life balance by scheduling your late-night Slacks with Message Them Later.

This free Slack app allows you to schedule messages into the future both out of courtesy for working hours and as a way to schedule reminders for your team meeting in advance. The developers created this app for “bosses who like to constantly ask for stuff, but want to minimize complaints about work/life balance,” but we also love it for scheduling reminders from yourself to yourself to take a break or submit that credit card statement on time!

After adding the app to your Slack workspace, simply type /schedule followed by the message and the date and time you want the message to be sent. For example, type /schedule Hello @channel! Reminder that our monthly virtual happy hour starts in 15 minutes! 4:45 pm and press enter. You can also use natural language like /schedule Do you wanna make a call? in 5 minutes or simply send /schedule and a window will open where you can compose your message, choose the date, time, and destination within Slack.

Remote Team-building Hacks

How do we cultivate company culture over tools like Slack and Zoom? Long-term remote worker productivity is directly related to camaraderie and positive company culture, so we’ve included some tools that help foster company culture via automated daily interactions, plus our suggestion for a fun, engaging virtual happy hour.

Donut is a bot that strengthens your team’s relationships, culture, trust, and collaboration.

Whether you opt for virtual coffee roulette between coworkers or a virtual watercooler channel to spark team-wide discussions, Donut will automate the team-building activities for you.

With goals like “Banish Social Isolation” and “Take the Watercooler Virtual,” Donut helps combat burnout by encouraging socializing across time zones and departments with prompts that inspire thoughtful conversations—and even the occasional friendly debate. Although remote teams might not be together in an office, serendipitous social interactions are still meaningful and help build happier, more productive teams. Add @donut to your Slack workspace and watch the connections blossom over virtual coffees and lunches!

DailyBot is a bot that automates daily check-ins and teammate recognition.

DailBot keeps remote teams aligned and facilitates deep work by reducing the need for meetings via automated daily standups, team check-ins, and periodic surveys (read: fewer video calls!). To help build camaraderie in your virtual team, DailyBot allows teammates to send and receive kudos, earn rewards for their outstanding work, and track overall team motivation. 

After adding DailyBot to your Slack, Microsoft Teams, or Google Hangouts, team members will be automatically prompted to submit updates covering their recent achievements, plans for the workday, and where they may be getting stuck. It will also ask how they are feeling and if they need any assistance. Through kudos leaderboards with optional rewards or fun games, DailyBot automates the celebration of wins and creates a culture of recognition and continuous improvement for a more productive and connected remote team.

BirthdayBot is precisely what it sounds like: a delightful bot to help your team celebrate birthdays and anniversaries!

By adding BirthdayBot to your Slack Workspace, you can automate the celebration of every team member’s birthday or work anniversary without lifting a finger. Since we can’t all gather around the break room and sing to you over cupcakes, this little bot is a thoughtful and easy way to make your team feel appreciated and connected to one another. 

Last but certainly not least, meet your new favorite happy hour host: Lounge.

With video meetings dominating work hours, the last thing your team needs or wants is another video meeting in the name of team-building. By adding Lounge to your Slack workspace, you’ve handled the next virtual happy hour’s RSVPs and event reminders, as well as leveling up the event with in-Slack games like Codenames, Werewolf, Pictionary, WTF—What  The Facts?!, and Alien Invasion.

One of remote workers’ top requests is to stop making everything a video call—this includes fun events! Lounge lets you connect from your phone or desktop in a virtual space with built-in audio, quirky avatars, and more. Plus, you don’t even have to play to join in on the fun! Hop around game rooms to chat with your team, spectate, or join the ongoing game.

Onward: Prioritizing Company Culture

As we lap the one-year anniversary of COVID-19 quarantine and the massive, global shift to remote work, Outlander VC’s team dynamic has become the new normal: an entirely virtual team working from homes around the world. 

We encourage company leaders to invest in making this new normal as seamless and positive an experience as possible for their teams by prioritizing services that foster meaningful connection and simplify collaboration. The productivity of both in-person and remote work is influenced by the same key factor: positive company culture. Workplaces that prioritize strong company culture can have high employee productivity no matter where their desks may be.

For February’s Outlandish Speaker Series, we spoke with Lo Toney of Plexo Capital.

Lo Toney is the Founding Managing Partner of Plexo Capital, which he incubated and spun out from GV (Google Ventures), based on a strategy to increase access to early-stage deal flow. Plexo Capital invests in emerging seed-stage VCs and invests directly into companies sourced from the portfolios of VCs where Plexo Capital has an investment. 

Prior to founding Plexo Capital, Lo was a Partner on the investing team at GV where he focused on marketplaces, mobile, and consumer products. Before GV, Lo was a Partner with Comcast Ventures, leading the Catalyst Fund and working with the main fund focusing on mobile messaging marketplaces. He also worked with Zynga as the GM of Zynga Poker with full P+L responsibility for Zynga’s largest franchise at that time. During his leadership, web bookings increased by over 150% with margin expansion. Lo has also held executive roles with Nike + eBay as well as startups funded by top-tier investors.

Lo received his M.B.A. from the Haas School of Business (University of California at Berkeley), where he completed the Management of Technology program: a joint curriculum program with the College of Engineering. Lo received his B.S. from Hampton University in Virginia.

Lo spoke with Outlander’s Paige Craig about investing in emerging managers, diversity in venture capital, and the future of work. Listen to the full conversation or hit the highlights of our Q&A:

There’s been criticism by folks that the recent spotlight on diversity in corporate America and other institutions is all for show. In our world, what do we do to not let it be just for show?

This national conversation about race wouldn’t have really gotten to the point it’s at today without the unfortunate events of last summer. Without question, I think everyone can agree that this wave of protests felt different. But I also think there is a feeling—and I’ve heard it and I feel it as well—that it may be kind of waning now, that it is just a moment. We don’t want that to happen. We want to see it turn into a movement.

So we’re staying focused on these issues, especially in highlighting the great things that happen when we can get capital into the hands of these Black GPs who data shows often have more diverse portfolios than their peers. More capital into the hands of diverse GPs is more capital into their more diverse portfolios, and once their portfolio companies get access to that capital to execute their strategies, those diverse founders also go down a wealth creation path which ripples out into their communities. 

Data also shows that these diverse-led companies also end up hiring a more diverse early employee base. And when those diverse employees have access to capital, the opportunities change for them because they’ve got a financial backstop they didn’t have before. They can go and start a company or invest in one of their peers. And then capital goes back to the GPs, and if the GPs have enough liquidity events, they go down the wealth creation path and capital goes back to the LPs. This model leverages a great strategy to drive alpha and produce returns with the by-product—which I’m really passionate about—of diversifying the ecosystem is working, and we should all triple down on this.

And this is very similar to what happens in a geographic ecosystem, right? Just look at what’s happening in Atlanta: money paid to employees of bigger businesses is used to start companies investing in early-stage startups, thus creating a whole ecosystem for startup funding. Atlanta is really interesting because we can actually see that vertical ecosystem built around people of color, Black people in particular. So, I look at places like Atlanta as a kind of proof of what can happen when there’s inclusion at the earliest stages of the development of an ecosystem.

“Atlanta is really interesting because we can actually see that vertical ecosystem built around people of color, Black people in particular. So, I look at places like Atlanta as a kind of proof of what can happen when there’s inclusion at the earliest stages of the development of an ecosystem.”

— Lo Toney, Founding Managing Partner, Plexo Capital

With the recent attention on funding for Black founders, are we actually seeing an increase in funding for Black-led startups?

Based on all the individual anecdotes that I’ve seen, it is clear that more capital has gone into Black-led companies within the past 12 months, but not as much as we would like. I’m anxiously awaiting the actual data to come out because I think what we’ve seen is probably an increase, especially in later-stage companies like Calendly in Atlanta or Squire in New York. The most visible examples have been at the later-stage companies, where we had never really seen any dollars go into Black-led companies at the later stages before.

Part of the problem is also the lack of Black venture capitalists. Then within the Black VCs, there are even fewer Black limited partners, and within the Black LPs, there are only really two types: the majority being professionals that work for the endowments and foundations of the world and the minority of Black LPs are people like me who are controlling their own pool of capital. And we don’t tend to see as much activity by the pension funds in early-stage venture capital due to their obligations and liabilities to their constituents.

One of the recurring obstacles I hear about from diverse emerging managers is the fee structures—especially for smaller funds—and the GP commit. What’s your advice for how they pay themselves and deal with the GP commit?

First and foremost, this is an issue that actually keeps a lot of potentially great GPs out of the market. One of our GPs actually told me about pitching a prospective LP—a retired venture capitalist—who listened to the GPs challenges and said, “Well, maybe you’re not rich enough to be a VC.” And I was shocked. First of all, there’s no data that I’ve seen that says the richer you are the better of a venture capitalist you’re going to be, right? But, to your question, there is a financial reality to being a successful venture capitalist as well.

We’ve estimated that it takes about $1-2M to get things rolling. And how do we get to that number? Well, it’s a combination of things. For one, foregoing their salary for what we estimate will take about 24 months from the time that a data room is open with an LPA until the final close happens. They’ve got to finance their lifestyle so they can focus fully on raising a fund, which is really difficult especially for an early manager. If you’re an emerging fund manager, you might have 50 LPs to 100 LPs, and that alone takes a lot of hustle over a long period of time even pre-pandemic. There are travel, pre-marketing, and hiring expenses, not to mention one of the bigger expenses, if it’s not able to be deferred, of legal aid for fund formation. All of which a GP is paying out of pocket. Then, once that first close happens, there is the ability to recoup fund formation.

Usually, for a smaller fund, I’d say you probably no more than $250K or so. You’re likely not going to recoup any of that lost salary or travel expenses, but the legal expenses are non-negotiable. And to your question, Paige, your salary is not going to be what it was—if you’re lucky, it’ll be half or maybe a third until you can stack a couple of funds to have stacked management fees. And, then, you’ve still got to turn around and pledge 1-2% as the GP commit, which is a significant financial hurdle for a lot of people to enter the space.

I’ve seen people handle this a little more creatively than how I answered above. I know I was lucky in that I was able to basically be an entrepreneur in residence while I was working on my fund at GV. And if you can find an opportunity to work inside of a fund, I highly recommend doing it to get a little bit of salary and a little bit of infrastructure as you build. And to touch on diversity again, that’s a great way that firms can help diverse emerging managers, right? My other recommendation is to see if you can defer your legal fees. If you can go to one of these larger shops, they might be willing to defer the legal fees, which is a big help to not have to pay those until after there’s a close.

“One of our GPs actually told me about pitching a prospective LP—a retired venture capitalist—who listened to the GPs challenges and said, “Well, maybe you’re not rich enough to be a VC.” And I was shocked. First of all, there’s no data that I’ve seen that says the richer you are the better of a venture capitalist you’re going to be, right? But, to your question, there is a financial reality to being a successful venture capitalist as well.”

— Lo Toney, Founding Managing Partner, Plexo Capital

Do great investors make great fund managers?

At the end of the day, our objective is to make sure our Plexo Capital GPs can make that transition from being a great investor to a great fund manager. And there is a difference. It’s one thing to be able to pick and support portfolio companies, but a whole other ball-game having investors in your own fund and managing that process with other people’s money. For instance, it requires having lawyers craft the LPA, negotiating that LPA to meet objectives with the investors, creating a cadence of communication that makes sense for your investors, reporting that gives your investors the information that they need, the insight into what it is and isn’t working with our strategy, putting together a go-to-market strategy for a fundraising process, and more. All of those things don’t really have anything to do with being a great investor. Those are skills of a great fund manager, which is what we’re really trying to help our GPs transition into.

Say you’re an emerging fund manager who’s allocated most of Fund I. Things are still coming to fruition but you want to raise Fund II at a higher AUM to keep up the momentum. Do you double down on the thesis of Fund I? Or reframe to share learnings from Fund I and how you’re adjusting for Fund II?

It really just depends. My first thought is that this goes back to something called strategy drift, which is when a company doesn’t change with technology or with competition and continues to do business the same as it always has been doing it. And the one thing that LPs don’t want to see is strategy drift. For instance, when you look at the data about what actually produces the majority of manager churn inside of a portfolio, it’s not usually tied to any fund performance metrics but more often a combination of strategy drift, general partnership issues, and poor communication—all elements that really are more about whether or not you’re a good fund manager, not a great investor.

So, my feedback for this emerging fund manager is to go in with a thesis and a strategy, then execute against it. In that strategy, there must be lessons learned in Fund I that are going to support the elements of the strategy of moving forward into a successor fund as well as any required modifications. The key is the ability to be able to provide that insight to the prospective investor as to why these decisions are being made, so really focus on being consistent in your strategy while also recognizing and adapting the lessons learned in Fund I.

Also, keep in mind that a lot of times when a fund manager is interacting with an LP, the LP is going to want to build a relationship over time because we’re preparing for multi-decade relationships. And it may be the case that the LP looking at the current fund is not going to invest until the next fund because they want to see a full cycle, right? Your ability to demonstrate the lessons learned in Fund I that made you stick to your strategy and even make necessary tweaks to that strategy is critical to building trust with your LPs.

In light of the global pandemic, what industries are you most interested in watching right now?

When I think about the things that were gaining traction pre-pandemic, there was a lot of focus on delivery services that enabled consumers to reclaim their time. Then from an operational perspective, we were thinking about the fundamental shifts and logistical measures that needed to happen to get those things to consumers quickly and with minimal effort on their part. 

For example, we’ve invested in this virtual kitchen company, which looks at all the data around people’s preferences for types of food, where those people live, and then creates a hub-and-spoke model with ghost kitchen restaurants that look like they’re brick and mortar in terms of their online presence. But they’re not! They’re solely geared towards UberEats-style delivery. Pre-pandemic, we saw these ghost kitchens climbing higher and higher on the algorithm because of all the data that they’re using to understand preference and location. Then the pandemic hits, and all of a sudden there’s a steep rise and increase in demand for that type of service. 

For consumers, there’s been an acceleration in these delivery services, as well as anything to do with the screen. Driven by the insatiable demand for content from Netflix, Amazon Prime, and Disney+ and the uptick in playing video games together and remotely, the demand for an infrastructure required to be able to deliver those services has also increased.

On the enterprise side, think about all of the naysayers that were laggards when it came to accepting remote work and a distributed workforce. There was a psychological barrier as well as a financial barrier because even if people agreed that it was going to be productive, they didn’t necessarily have the infrastructure in place to be able to support remote work or a distributed workforce. But then the pandemic hits, and now the naysayers have been forced to deploy billions of dollars into building that infrastructure. It would have taken years to get the investment that we’ve seen into all the infrastructure required to have a secure system for remote access work, but we’ve seen this massive acceleration when the pandemic first started.

We’ve seen massive amounts of money going into these different services for both consumers’ and for enterprises’ new normals, which I think are likely going to persist long-term. That’s where a lot of new opportunities are going to happen. The downside, of course, is that these great new innovations are juxtaposed against the pain and suffering of so many people across the globe. So, for investors, it’s really important to think about the things that we can invest in that can help narrow socioeconomic gaps as a by-product of what they do as opposed to widening those gaps.

For us, Talli has always been love at first Demo Day. 💙

In the fall of 2020, Outlander VC’ Founding Partner Leura Craig happened upon Lauren Longo pitching at Launchpad2X. Immediately, Leura was intrigued by the badass female founder determined to help new parents with innovative, intuitive tech. With Lauren’s background in user experience and software product management—coupled with her husband John’s software and hardware development background—they created the first Talli device as a way to stay afloat during the overwhelming first months with a newborn.

As Lauren and John spoke with friends about how they were keeping up with new-parent life via a simple button device they’d built, they realized they’d built something other parents needed too. Putting their technical skills to work, they developed their concept into a beta version of the Talli device—all built inside plastic storage containers! They sent the beta device out to 30 families across the US, along with a web application they’d built to record and analyze the device’s event data. After receiving overwhelmingly positive feedback from their beta testing, they decided to go all-in getting Talli ready for market, bringing on long-time colleague Patrick Caldwell as Talli’s CTO to work with Lauren as CEO. 

From the beginning, the Talli team has received frequent requests from other segments of the caregiving market who wanted Talli to help them, too: parents of older children with special needs, people struggling with diagnosis and management of chronic diseases such as epilepsy, and adult children managing the care of aging loved ones. Talli has laid the groundwork for their platform to easily expand into these additional segments, building the entire Talli platform for easy reconfiguration. 

Next week, Lauren and Patrick will present at Outlander VC’s inaugural Demo Day, bringing the meet-cute story of Outlander and Talli full-circle. To mark the occasion, we’ve asked both Lauren Longo and Leura Craig to reflect on Talli’s journey since that pitch in the fall of 2020 and how they foresee Talli changing even more lives in the next 20 years.

Why does the world need Talli?

Lauren Longo, CEO, Talli: Millennial parents have grown up as master multi-taskers with technology streamlining their professional and personal lives. With a growing number of couples working toward a seemingly-elusive work-life balance while also raising children, more and more parents are turning to tech for new ways to solve age-old parenting dilemmas: sharing the load of feedings, diapers, sleep, and day-to-day care, while also monitoring overall health and development; finding success with breastfeeding (a common hurdle new moms face); establishing sleep schedules that are healthy for baby and supportive of parents’ mental and physical health; and more.

Traditional pen and paper tracking can more-or-less get the job done but are a little clunky and obviously have zero automation for getting the data into a useful summary to show trends and patterns. Baby tracking apps have emerged in recent years as the next step; however, logging events in an app is a multi-step process and requires you to have your phone with you in the first place—neither of which is ideal in the 24/7 whirlwind of infant care. Plus, this method requires all of your child’s caregivers to be relatively tech-savvy, which can be difficult for nannies, grandparents, and other caregivers to access and update, preventing consistent tracking of care when Mom and Dad are away.  

Talli’s simple, one-touch device distills the multi-step logging of these apps into the press of a button. It’s quick and easy for parents, freeing up time and mental space in their daily routine, and it’s intuitive enough for grandparents and nannies, enabling consistent tracking of care across caregivers. And we’ve even added an Alexa skill for hands-free logging as well! From the Talli device or Alexa skill, baby’s events are logged in our app, where all data appear in real-time from anywhere.

What does the future of care look like with Talli? 

Lauren: In the short-term, we are planning to unlock full customization features this summer, which will allow parents to extend the use of their Talli beyond the infant phase. Once Talli is fully-customizable, the sky’s the limit for what our customers can track and for other markets we can serve.

With that being said, we envision Talli providing simple tracking across the care tech market: infant care, senior care, chronic conditions, and animal care in B2C and B2B channels. We also envision our customers publishing their own Talli configurations that helped them and that others can download and use, such as configurations for smoking cessation, plant care, daily chores, workout routines, etc.

We know that caregivers across industries are facing increasing demands for data entry and tracking, in addition to increased patient loads. It’s approaching an untenable situation, reflected in high turnover rates and staffing shortages. We believe that simplifying the logging of repeated care activities to the push of a button will expedite the data-entry process for overworked staff and allow them to improve the consistency of data being tracked. In this way, Talli can help staff focus on the quality of care and improve the health outcomes of the people they serve.

Why did you and your co-founders decide to pursue Talli?

Lauren: First and foremost, we’re parents, so we know from personal experience how difficult and overwhelming that first year is with a new baby. We know how important and daunting it is to try and keep up with everything from shaping a symbiotic sleep schedule to getting the hang of feeding (especially breastfeeding) for both baby’s development and a parent’s peace of mind that you’ve got this under control.

We’ve spent our careers honing technical skills for finding the simplest ways technology can solve a real-world problem and then implementing those solutions. But, until Talli, we were applying these skills to things like budgeting systems and time card management. These are real business problems, for sure, but Talli is our opportunity to improve the day-to-day life and well-being of families throughout all of the wonderful and challenging stages of caregiving. 

“We all truly believe Talli is something the world needs, and we believe there’s nobody who would do it better than us. ”

— Lauren Longo, CEO, Talli

What formative experiences do you believe primed you for a life of entrepreneurship?

Lauren: My dad has been an entrepreneur for the last 30 years in various cleaning-related businesses. Until my sister and I forced him to stop, he was famous for taking a sip of his organic and environmentally friendly multi-purpose cleaner on sales calls! He’s had his share of both success and failure as an entrepreneur, so he has been a wonderful source of advice and support to me in this journey. 

My mom spent her entire career teaching students with hearing impairments and special needs, and she always went above and beyond to support her students’ families outside of school. I was lucky enough to be directly involved in her work for much of my childhood, which really instilled in me a drive to help others wherever I can.

What has been the hardest thing you’ve faced as a founder? How did you tackle it?

Lauren: In short: 2020. From a business perspective, the pandemic disrupted our production and we were forced to delay our Talli Baby launch. Plus, our team has now worked remotely from homes full of kids running amok for much of this year as well. I can attest that being a full-time working mom with both of my kids at home has certainly leveled-up my ability to multitask and increased my capacity for stress!

At the same time, my kids have always kept me focused on the “why” of Talli, and they’ve been very involved in this journey in their own ways. We hope to instill in them lessons around perseverance, work ethic, and never giving in to fear by modeling those behaviors through this venture.

As an investor, what drew you to Lauren and Talli?

Leura Craig: When I first saw Lauren pitch at Launchpad2X, I was immediately intrigued by the potential of such a huge and relatable problem—one which Lauren had faced herself—that Talli was seeking to solve with intuitively simple software and hardware. As an investor, I really value founders with category-expertise who develop their solutions out of their own experiences. When you’re solving a problem you’ve faced, the motivation and drive behind your venture is extremely personal, and that’s why you want to solve it.

When I reached out to learn more about Talli, she told me about a night when she broke down sobbing because her doctor wanted her to track all of these data points and metrics so they could understand how her first child was growing and evolving. And this is a common thing that pediatricians ask for because a newborn’s eating and sleeping routine is critical to their development and growth, right? But like all new parents, she was feeling overwhelmed and couldn’t figure out a way to keep track of all that information, so she decided to build a better way.

I mean, she literally built a better way. After learning more about what Lauren and her co-founders were developing with Talli, I was not only impressed with Lauren as a brilliant, organized, and driven founder, but also that they had already managed to create and test their hardware prototype. Hardware is a notoriously difficult category for tech startups. Many ventures run into issues figuring out 1) how to build a prototype, 2) how to test it, 3) when do you get users to test it, and 4) and when do you evolve it to the next generation. But Lauren and her co-founders, through thoughtful iterations and early user testing, developed a very sticky product that people absolutely love.

What is compelling about Talli’s hardware + software solution?

Leura: Well, to start, one of Lauren’s superpowers is her eye for branding and UI/UX, which is so important in a solution aimed at ease-of-use. To have hardware that’s intuitive and elegantly designed paired with incredibly intelligent software is a game-changer in the category of baby care. But what was also compelling to me as an investor is that they’re not stopping with baby care. We’ve already seen how quickly and organically Talli’s baby care platform has grown, so we are anticipating a similarly enthusiastic response when they branch out into other categories as well.

Talli’s event logging solution can easily be applied to senior care, pet care, fitness routines, medication and symptom management, and more. But in the bigger picture, it can also be applied to B2B manufacturing or any other category of business that could benefit from smart recommendations based on tracking events. In my mind, there are endless use-cases because they’ve intentionally designed it to be content-agnostic. Talli can help people be more mindful and productive, while also enabling them to reflect on the trends of their lives based on their logged-events. That’s why Talli is such a powerful solution: it can be applied to anything.

Why should others invest in Talli?

First and foremost, I believe that other investors should invest in Talli because they’ve proven to be an exceptional early-stage company a la Outlander’s Founder Framework: the founding team has already proven they have the vision, intelligence, character, and execution to build a multi-billion dollar company. Lauren and her team are not only extremely dedicated, but they have also demonstrated they have the outside-of-the-box creativity, problem-solving, and grit necessary to navigate the challenges scaling will inevitably bring. 

In the last few years, consumer hardware has been neglected by venture capital. Because of this industry trend, I worry that investors will be hesitant to embrace the potential power hardware can have in solving consumer problems, especially when combined with great software. So, to all my fellow investors who love consumer products: get excited to meet Lauren and her team! This is one of those types of companies where if they get it right, Talli will change the way we think about event tracking tech solutions for good.

“This is one of those types of companies where if they get it right, Talli will change the way we think about event tracking tech and solutions for good.”

— Leura Craig, Founding Partner, Outlander VC

TALLI — hardware + software for one-touch, mobile, hands-free logging health care

Our mission at Talli® is to reduce the mental burden of caregiving through easier logging of care and health data. Our flexible IoT platform provides hardware and software options for one-touch, mobile, and hands-free logging across infant care, senior care, and home health markets. Talli is flexible enough to track any type of event and then translate that data into actionable information and the insights you need most.

Based in Atlanta, GA, co-founders Lauren Longo and Patrick Caldwell are disrupting the tracking and sharing of health and care data through an IoT logging and health data platform with configurable hardware and software solutions.

To learn more from cofounders Lauren Longo and Patrick Caldwell about Talli, register for Outlander VC’s inaugural Demo Day on March 2, 2021 at 4 pm EST.

© Outlander VC. 2022.