Sam Jacobs

I just wrapped up a panel with the Marketing Leadership affinity group within the How Women Invest community with my hero Auntie Nancy Hayes, aka the Yoda of board membership, angel investing, and general badassery. We talked about different ways to serve on boards, a role in which experienced Marketers seem to be often underrepresented. Why? If I had to guess, I'd say: 1 - Most heads of marketing are women 2 - marketing is undervalued, especially under sales/revenue experience 3—Compound the first two with the messages you tell yourself about your own worthiness, and suddenly, you're a great marketer for everyone else but yourself. ___________ For those who are interested in getting closer or into the board room, there are so many ways to start/get experience: 1—Board Observer (one of my current board roles)—you represent the investor but have no votes. It is unpaid, but/and hugely essential to act as a bridge of visibility and communication between the fund you've invested with and the company in which the fund has invested. My role brings value to both sides with much less bias than the other VC board seats. 2—Corporate board director—There is much governance but not much influence on the product, as the company usually has big enough teams for that. There is a lot of hiring/firing CEOs (read: drama), which can still be fun, especially for those fresh-popcorn-in-my-bag swag kinda folks (both grossly generalizing and way understating this role's fiduciary importance, but you get the idea). 3—Independent board director—this is another of my favorite places to sit. It is much like the Board observer role but with voting rights and equity (although not always, as these terms are negotiated and influenced by the shareholding board seats). You are NOT representing a VC fund (typically), but you might have subject matter expertise in the product or are a generalist boss gal like myself and bring a sense of neutrality and balance to the board. 4—Advisor. Advisors are similar to IBD in terms of influence and type of advice but are not part of the board or its meetings. This role is usually paid in some combination of equity and cash. It's another of my faves. (Are you seeing the trend here?) We have not even touched non-profit boards (where I got my start and am currently sitting on my sixth), but we will save it for next time as it's a whole 'nother Oprah. If you want to learn more, How Women Lead is hosting its 5th annual #getonboard week, starting October 21. Hybrid virtual and in-person. Check it out: https://lnkd.in/diizwv8j #womeninleadership #boardofdirectors #howwomenlead #governance #boarddiversity #corporategovernance #boardservice #businessleadership #leadership Julie Candelon Susan Greenwood Schroeder Mikayla Ludwig

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Advisory boards have been pivotal throughout my career, and this new report from the Boardstream team is a must-read. It’s packed with actionable insights on how to build and leverage an advisory board that truly drives impact and growth. Well done, Evan Kraut and Marina Ilishaev! 👉 https://lnkd.in/dPTAS4-Y #AdvisoryBoards #CAB #Leadership #Boardstream #WhitePaper

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Great time on the Embracing Erosion podcast w/Devon O'Rourke! We talked about: 🚀 How to scale a company from concept to 9-figure exit 🔄 How to break away from the traditional consulting model and apply product approaches ⏩ Why it’s important to iterate quickly and often with messaging 💸📈What signals are important to pay attention to when investing in startups and much more!

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The secret—if it ever was one—is out on private equity fondness for vertical software. While PE-backed acquisitions were down 50%+ from a peak in 2021, vertical buyouts have continued to grow, and the fervor seems to be gaining steam. In today’s essay, we will pose an answer to one question: is PE a viable path to exit for a venture-backed startup?

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Many SaaS solutions resonate most with directors/VPs/department heads. For the past 5+ years the approach for selling to these folks was to get them very excited about your solution and price in such a way that they could get a deal done with minimal sign off. In enterprise this could run as high as 500k. Now, there is scrutiny on 25k deals. Smart sellers realize this and are running a totally different play. A little different flavor of the traditional top down model. These folks are still doing well. Folks running the old playbook? In struggleville. P.S. - when times are hard it’s actually easier to do big deals…if you know how to sell transformations.

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Rolling into another day of the Primary Summit. Hit me up if we should connect onsite. Kudos to the Primary Ventures team so far, as yesterday’s Pre-Seed Summit was on point. Mar Hershenson, Benjamin Sun, Chris Douvos, Zach Weinberg, and Graham Pingree all dropping helpful nuggets for fund managers. Some paraphrased highlights: - Chris Douvos (AHOY Capital) - Most fund decks are terrible. Start with your people (not your strategy) and know you have about 6 slides of his attention. - Zach Weinberg (Curie.Bio ) - beleives SF’s AI talent is a significant advantage over NY, wouldn’t build AI in NY. Also questions if VC exits can keep up with VC expansion (generally hilarious and smart Twitter follow) - Mar Hershenson (Pear VC) - VC is so much more competitive now. It’s not enough to be an ex-founder with a great network and domain expertise. Have a better “why you are different” or do something else! - Benjamin Sun (Primary Venture Partners)- still sees arbitrage in going long NY venture (vs. SF). Do the work to keep various influential networking nodes aware of what you’re doing and how you think.

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🧨Co-Syndicating & Scouts → the best source of Deal Flow for (the most active) Syndicate Leads 🧨 I spoke to a prospective Deal Sheet customer this week who was asking Zachary and I about sourcing and accessing deals. Part of my response was similar to any VC i.e. networking and sharing deals with other VC’s, having built a large portfolio of founders who introduce their founder friends etc. But in this (odd & different) SPV ecosystem, co-syndicating & working with scouts (or at least the incentive w/scouts) are 2 unique sourcing channels. 1) Co-Syndicating The alignment & shared incentive makes co-syndicating the best deal flow channel for me, and many other top syndicate leads. So, why is co-syndicating deals unique to syndicates? Strong alignment of incentives here. Unlike most institutional funds, syndicates do not have target ownership as we are more flexible and simply focused on investing in the best deals, across stages. For that reason, syndicates tend to share deals within one another to team up frequently. Whether it’s taking down larger allocations or carry-share incentives or paying it forward knowing your co-syndicate partner might bring you into the next deal, it’s been proven to be a great way for syndicates to collaborate. 2) Scouts While working with scouts is nothing new to traditional VC’s, the incentive for scouts working with syndicate leads can often be more attractive. Syndicates can typically be more generous with carry sharing for scouts given they are not giving up carry out of their fund, rather on the specific deal. It makes it cleaner + easier. Generally speaking, the more active syndicates are able to invest in more companies than a traditional VC. So scouts that truly have great deal flow can get a lot of carry shared on a lot of deals by working with syndicates. And as a syndicate lead, I’ll do that all day long to continue to access the best founders :) -- Powered by Sydecar, Last Money In Media is the most actionable venture capital newsletter. Written by Zachary Ginsburg and Alex Pattis who have deployed >$200M across 750+ SPVs.

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🌱 For founders taking on venture debt, covenants are the fine print you cannot afford to ignore. 📃 They set the boundaries for how you can operate and manage your company’s finances. If you don’t play by these rules, the consequences can be pretty dire. It’s all about negotiating terms that align with your startup’s financial health. Be sure to read the original post by Kruze Consulting to get the full breakdown. Link in the 1st comment. 👇 #StartupFinance

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Halle Kaplan-Allen and I will be chatting with Ali Hamed tomorrow about sourcing LPs. You can RSVP here: https://lnkd.in/edYZhKrA Ali wrote this excellent tactical piece on networking that is well worth a read for anyone networking their way to capital: https://lnkd.in/eZ_2f_4x This event is presented by Sydecar, a frictionless deal execution platform for venture capitalists. By pioneering a standardized approach to private investing, they enable capital allocators to identify and back entrepreneurs who are changing the world. Their platform reliably handles back-office operations, automating banking, compliance, contracts, tax, and reporting so that customers can focus on making deals and building relationships.

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When stuck in a scenario where revenue is growing at a moderate pace, but not fast enough and burn is putting the pressure on getting to the ARR target of $1M+ faster, Founders need to find a way to grow revenue quickly. One thing Founders get advice on is “increase the deal size and you only need X deals to get there.” The problem is, it’s not just about hitting a revenue milestone, it’s telling the story of your ability to acquire and grow your customer base for the next 10+ years. 

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The new episode of The Science of Scaling Podcast dropped today. In this episode, I speak with Ang McManamon the VP of Sales at Crunchbase. We dissect managing sales through a pivot, specifically how she managed the team as the market transitioned from one of the most bullish markets in tech in 2021 to one of the biggest down markets in tech in 2022. Example discussion points include: How to manage a board that is demanding an unrealistic revenue target? (1) Educate them on the current bottoms-up GTM model by showing them where the team has been performing on the key drivers of revenue outcomes over the past 2 quarters (i.e. the average productivity per rep (PPR), MQLs generated per month, average sales cycle and close rate on sales opportunities, etc.). We implement this framework with our portfolio companies Stage 2 Capital before issues like this even surface in order to establish the narrative from the beginning. (2) Illustrate where these metrics need to be to achieve the revenue outcomes they are demanding. Often this analysis yields the conclusion that the team would need to 2x PPR, MQL generating, and and close rates essentially overnight. Hopefully, they start to see how unrealistic the plan is and that the plan is going to lead to unnecessary burn and departures of top performers (3) Using the bottoms-up model, devise an aggressive but realistic plan that assumes say a 10%-20% Q/Q improvement in each of the performance drivers and the revenue outcomes that this performance would yield. (4) The board may ignore this line of thinking but at least we have educated them on the revenue mechanics and can use that framework to report back results at the next meeting. How to quantitatively assess whether a revenue miss is due to a macro condition, like the economy, or sales execution, like hiring and training the salespeople? An area few boards and leadership teams look at to conduct this diagnosis is the quarter-over-quarter performance of individual AEs, especially the consistent top performers on the team. If the company misses the target and you look under the hood and find that the historic consistent performers are still performing as usual and the miss was driven from AEs hired in the last year, we have a sales leadership execution issue. However, if we look under the hood and see that even the top performers' PPR decreased, perhaps at about the same time and about the same amount, then we have likely have a diagnosis outside of sales execution (i.e. economy, competition, product, etc.) Anyway, Ang is awesome and was completely open about this journey that so many leaders experienced over the past two years. Check out the episode here! https://lnkd.in/e2QiuPEH

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High costs and low margins are tough. They can really hold a business back. But there’s a way forward 🚀 By streamlining your processes, you can cut down on unnecessary expenses. This means looking closely at how you operate and finding ways to be more efficient. Also, it’s important to diversify your revenue streams. This isn't just about having more products or services, it's about creating stability. When one revenue stream falters, others can help keep us afloat. By expanding our sources of income, we reduce risks and enhance our financial health. ⭐Focusing on these steps will help boost our profits and build a sustainable future. 

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Founders, you're losing deals by not having a clear discovery call plan. I've seen this a lot where founders looking to scale up their early sales efforts are going into it thinking the product will get them through the sale In most cases, this isn't the truth You need to have some sort of framework to make the selling motion more repeatable Instead of demo'ing the product, try learning more about them and their challenges first. Your goal should be to know enough to build a customized demo for them. This will help in building solid relationships, build value throughout the process and likely speed up deals on the back end of it. If you don't know where to start, hit me up and I'm happy to lay out some early sales structure for founders! Go crush it out there 🤙

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I recently sat down with a group of Forum Ventures founders about to go out to fundraise and the topic of SAFE rounds came up. The context focused on the pros/cons of raising a priced vs a SAFE round and the conversation notably shifted toward the dilution implications of a SAFE round. Founders are keenly aware of the top line dilution of any funding round - ie selling 20% of their startup for $3M at a $15M cap - but very few fully grasp the implications of doing a SAFE round vs a priced round. The universal standard for institutional VC investors is a post money SAFE. This document essentially outlines ownership that an investor will have in a startup just prior to the execution of a priced round. Most importantly though, it is structured so that an investor in that SAFE will not be diluted by subsequent SAFE's that are issued. This is where founder education around the implications of this structure are not fully appreciated. In a situation where a founder continues to stack subsequent SAFEs, they don't actually convert until the first priced round and the net dilution they are taking is actually more than they realize. Here is a practical example - take a situation where a founder has already sold 15% of their business on a post money SAFE in a pre-seed round, and is now choosing to sell another 20% in a seed round. If the founder opts to raise this money on SAFEs, the dilution of that additional 20% will come entirely from common equity holders- meaning they will now own 65%. If SAFE holders were also diluted by that round, as they would be in a priced round, the founder would own 68%. This dynamic becomes more dramatic the more capital a founder raises on SAFEs. Note - this is a high level example and does not include an option pool carve out or other round nuances. Almost universally, when a founder raises their first priced round, there is some degree of sticker shock at the outright dilution on their cap table, particularly when options pools are factored in. This pain is even more acute when a founder has raised a fair amount of capital on SAFEs along the way. There are certainly benefits to raising SAFE round, mainly cash in hand 6-8 weeks faster and not having to decide on board seats too early, but I encourage all of our founders to run through cap table modeling and correctly account for the implications of SAFE rounds before they make fundraising decisions.

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Are you the hero in your business–or is your customer? In my conversation with Josh Cadillac on the Know Your Shit podcast, we talked about this mindset shift that can transform your business. Too often we focus on being the best, but we should be focused on being the most understanding about our customers. It’s about helping them make sense of their world, not just selling them a product/service. The key? 🔑 Listen to the episode to find out: Apple: https://hubs.ly/Q02VWk6Z0 Spotify: https://hubs.ly/Q02VWdB50 What strategies do you use to make your customers the heroes in their journey? #KnowYourShit #TheRevenueAccelerationFramework #CustomerSuccess #BusinessGrowth

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Here we go; Hampton's 2024 state of SaaS report is live. We surveyed our SaaS founders and got real answers on the state saas. The first thing I found surprising was How funding impacts time-to-$1M ARR (hint: not what you think) link to report: https://lnkd.in/gJmarrNa Give it a read and let me know what you think.

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The state of venture capital is wild right now. We are witnessing a surge of innovation across the spectrum: - Funds merging - VC doing PE - PE doing VC - Secondary funds - Buyout funds - Spin-out funds - Debt funds - Continuation funds - Infrastructure funds - GP turnover - Hard Tech surging - Family Office uptick

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